Trading mindset Archives - Data Driven Options Trading

A 112 Cautionary Tale

On August 5, 2024, the volatility index, VIX, spiked to 65, the fastest spike in Implied Volatility ever recorded. Anyone with significant holdings in naked options, including the 112, likely took significant losses.

The August 5, 2024 VIX Explosion Impact

In August 5, 2024 pre-market trading, the volatility index, VIX, spiked to 65, although the market was only down a moderate amount. The market had the fastest spike in Implied Volatility ever recorded, and anyone with significant holdings in naked options, and especially the 112, likely took significant, if not catastrophic losses.

Stock traders shrugged, but option traders, especially short in futures options, saw premiums explode to extreme levels. Short traders saw margin requirements explode and marked positions move to 10, 20, or even 30 times the initial amount collected in losses they couldn’t escape in illiquid markets.

The 112 trade, which is written about on this site in several places, was the poster child for big losses. Often traders use futures options that are leveraged to the max using SPAN margin. The trade promises to have a buffer of a 1-1 debit spread to provide a barrier from big losses in downturns. The 2 other short strikes are set to be so far out of the money that they should almost never get in the money for big losses. But this time it didn’t work- a fairly small downturn created huge losses and extreme increases in margin requirements.

Many seasoned traders I know saw their accounts reduced by 30-50% overnight with their brokers liquidating positions to satisfy margin requirements. In short, the debit side of this trade didn’t provide the promised protection during this event. Many traders, including me, saw big losses even though the debit spread didn’t even go in the money and the short puts were still well out of the money. It was the implied volatility that did the positions in, not the actual underlying market indexes.

Personal Impact

My experiences were mixed during this episode, but in all cases very eye-opening. I’ve done a lot of modelling of option pricing based on historical moves, the speed of moves, and other factors, and felt like I had a pretty good understanding of how volatility changes, even in big market moves. I survived the Covid crash, for goodness sake.

In most of my accounts, I had sufficient cash or cash equivalents to prevent a major problem with my account. However, I had one account that had two contracts of 112 positions that were using 90% of the account’s buying power before the big August 5 event (a bad idea in so many ways), and that account suffered a huge loss and was liquidated by my broker. I suffered a 250% loss, going from +$11,000 to -$17,000 overnight, which isn’t a small loss for anyone. My broker sold all of my short positions at the very bottom, in the early morning hours before the market even opened, locking in the losses, and then left the long spread positions to decrease in value as the market recovered, not allowing me to trade anything, due to having negative buying power in the account. It was a very helpless feeling to watch and see that much money evaporate. And then I got the email asking me to add money to get the account out of the hole. I asked why they had waited so long to close the positions, and why they didn’t wait any longer, but it isn’t the broker’s fault for this. It’s my problem and I have to own it. I simply got complacent and didn’t follow any of my own rules for capital allocation. I was greedy and I got burned- bad.

I wasn’t the only one, and in the aftermath, I read several option trader’s notes (that actually sell their trading advice) that lost years of profit during this event.

For all my other accounts that survived, the swings in value in accounts that had short options trading with margin was troubling and surprising. The fact that the values recovered as fast as they declined doesn’t change the fact that this could have been much worse and there are many lessons to learn.

For most stock investors, or even traders that sell option spreads or covered options, this event was no big deal. It was a problem for mainly for traders who sold naked options on margin, and especially for those that sold naked futures options on SPAN margin.

So, what actually happened, and why were so many option traders caught unprepared? Let’s dig into what happened, and then discuss how to avoid this kind of negative impact in the future.

The Perfect Storm of Fear

Markets were cruising to new highs in mid-July when it seemed that the market realized that maybe it was the time of year to finally step back and the market came down a bit. It was no big deal until August when the July jobs report came out on Friday August 2, showing very weak jobs data and an unexpected increase in unemployment. The market fell 1.8% during the day and there was a sense that the nation’s economy might be in trouble. Then over the weekend, foreign markets reacted, primarily in Japan, where the yen surged in value compared to the dollar, and many “safe” currency trades quickly unraveled. The Japenese stock market plunged over 12% in early trading, and the rest of the world followed along as other markets opened for Monday trading. With US Futures trading open, prices of all the indexes started down. Everyone trading wanted to get out, but there was no one available to bail them out. Futures options were the worst, with enormous bid-ask spreads with no one willing to make the market flow in orderly fashion. It was still the middle of the night.

Option traders awoke to alerts and margin calls from brokers. With an hour to go before the markets opened, buyers stepped in and started grabbing the bargain prices that were available, and selling short options for the astronomical prices that contracts were marked at, as brokers liquidated the unfortunate accounts of those who hadn’t cleared their negative balances. For those with cash, it was the opportunity of a lifetime. For those in trouble, some lost life savings over night. The best and worst of times.

When the market opened, it was down 3% from Friday’s close, but up from the worst levels of the night. It recovered about a percent in the morning but closed near where it opened. However, there was a sense that the worst had come and gone. Option prices quickly came back into somewhat normal ranges, and margin requirements relaxed. As the week progressed the market slowly eased up, day by day. By the end of the week, the market was essentially unchanged from the end of the previous week. Did anything really happen, or was it a dream? For almost everyone invested in the market, this situation was a non-event, a slight downturn, a bit of noise. But for Futures options traders that had naked positions, this was a never-to-forget nightmare.

By mid-August, it appeared that all the worries were for nothing. The US market moved back to near the record high levels set in July. Happy days were here again. But this isn’t normal.

Unprecedented Changes in Implied Volatility

In the past, increases in Implied Volatility have taken much bigger declines in the market for this big of a change. For example, during Covid, the market was down over 30% and the VIX volatility index hit 80 at the bottom after several weeks of large daily declines. The whole world’s economy came to a grinding halt and the market slid with it. At the time it was one of the most terrifying situations the world had seen.

In contrast, at the market’s lowest point on the morning of Monday, August 5, the S&P 500 futures were trading about 10% below the peak they hit in mid-July, and VIX sky-rocketed to 65. It was at less than 30 the Friday before. This rapid expansion in Implied Volatility over such a small timeframe and relatively small index price drop was unprecedented. Option prices multiplied in value and SPAN margin requirements for futures options increased exponentially. Brokers reached out in the middle of the night asking customers to add capital to their accounts, but from where, and how? Since the markets were closed, only minimal amounts of trading was going on and markets froze up with orders becoming unfillable. Trapped traders couldn’t get out, assuming they were even awake and aware of what was going on.

Likewise, the decrease in the VIX volatility index over the next few weeks was also remarkable. By August 16, the VIX index was below 15. Historically, large increases in volatility take months or even years to return to low levels, so this spike from levels of around 12 in early July to over 60 a month later, then back to 15 in less than two weeks is different than anything ever seen before.

For those not familiar, the VIX index is calculated by the CBOE to measure the volatility implied by options on the SPX index with expirations around 30 days away. The VIX index is not tradeable directly, but there are tradeable options, as well as futures that can be bought and sold. VIX is often considered the market’s “fear gauge,” but technically it is an evaluation of how richly options are priced. Since options are priced based on known values, with the only unknown value being volatility, this measure of “implied” volatility impacts all option prices. The numerical value of Implied Volatility of any option is a measure of how much the market expects the underlying security or index to move over the next year, but pro-rated down to the amount for the time left until option expiration.

Margin impacts

Margin works in a lot of ways with options. See the article on margin to learn more. But margin as true leverage is most apparent when selling naked options. For naked short options on stock, ETFs, or Indexes, most margin requirements are based roughly on having 20% of the notional value of the underlying in the account to cover a big move. So, one option contract on a stock trading at $100 would have a notional value of $10,000 and a seller of a naked option would be required to have $2000 for every contract, or would use $2000 of buying power or capital for each contract. If the stock moved 5%, the margin would likely require another 5% of the notional value, which could be as much or more than the premium collected.

If a trader is selling naked options on futures, a different margin calculation comes into play, SPAN margin. SPAN margin is a complex formula, but basically looks at the futures options positions and calculates a worst-case one day move, based on the IV of each option and other factors. This is typically a much lower requirement than what is required for options on stocks and ETFs, so a trader can have a lot more leverage. However, this works both ways. When the market moves, additional margin can be required based on the amount of the move, plus the amount that the “worst case” increased to. On August 5, when VIX spiked to over 60, the worst case scenarios as calculated by the SPAN margin calculation exploded by huge amounts, in addition to losses in holdings that were highly leveraged. As VIX virtually tripled, buying power requirements for futures options also went up by triple or more, when accounting for losses on top of the increased SPAN margin requirements.

Many traders in turn faced margin calls from brokers, asking them to get buying power from negative values to positive. For some the only way to do this was to buy back badly losing positions at big losses at terrible prices with terrible spreads. As much as anything, margin requirements drove liquidation as much as price movement.

The lesson on margin with options from this event is to always have cash or cash equivalent positions that can be easily liquidated to have cash to cover all margin requirements. Even a trader with the worst naked option exposure positions would be alright if their account was 80-90% cash. For me, I had accounts that I had to sell short term bond ETFs to cover buying power requirements on August 5. Every account but one was fine.

Within a few hours of the worst of August 5, VIX dropped significantly, and SPAN margin requirements reduced as well. The question was a matter of whether each trader had enough capital to weather the storm.

Marked loss impacts

When implied volatility spikes, Vega raises the price of options. On a percentage basis, the impact is greater for strikes further out of the money. For the 112 trade, the “1-1” portion of the trade that includes a 50 point wide debit spread has both strikes increase in price, fairly close to the same amount, while the two far out of the money strikes also rise substantially, but with nothing to cancel out their rise. The overall impact is that the total premium can grow much more than even the percentage increase in Implied Volatility. This is especially true if the positions were opened during a period of very low IV.

So, for a trader that opened a 112 trade when IV was down around 12-13 VIX, the explosion to a VIX of over 60 made the position’s premium value explode to 10-20 times what was collected, something that most traders would never have expected.

Position size considerations and notional value

With the 112 trade on /ES futures, a trader can use as little as $5000 buying power to control $500,000 of notional value. Even at very low Delta values for the 2 short strikes, it doesn’t take a very big move down to lose way more than the initial buying power. As we’ve just discussed, a big move causes two immediate problems for the trader, a marked loss as premium explodes, and an explosion of buying power requirements.

What is the solution? Keep trades like these a small portion of an account. The vast majority of the time, these trades just decay, leaving the seller with great profits, but when that rare occasion occurs, there needs to be plenty of capital in an account to cover losses and have the ability to manage the position.

Impact of the number of net naked options

I’ve tended to trade mostly covered positions and spreads, where this kind of scenario can’t happen because risk is defined, and a position can’t lose more than the buying power it requires. But it is easy to be persuaded by the siren call of those that tell traders to put on their big boy pants and sell naked options. Somehow, this is considered by some to be the mark of a mature option trader.

Often, traders are told that the buying power required is a good indicator of the risk of a trade. I’ve seen dozens of studies that make this claim. But typically, if you look at the fine print, these studies will say something like naked trades don’t lose more than their buying power 99.5% of the time, or some other high percentage. The problem is that the percentage is not 100%, and that little percent will surface on rare occasions, usually when least expected, immediately after a period of very calm markets.

The key isn’t to completely avoid naked trades, it is to manage the number of naked contracts being traded. During the August 5 event, 112 traders were much more impacted than 111 traders. The difference was two naked puts instead of one. Does that mean traders can load up on 111 and be fine? No, it just means that comparing two trades that both use naked options needs to account for the number of contracts that are naked and the difference in notional value and tail risk. Maybe the 112 trade has a slightly better return on capital typically than the 111. Is the additional risk worth it?

And it isn’t just the naked portion of multi-leg trades that need to be considered. Individual naked trades, as well as strangles or straddles sold naked can be even more susceptible to tail risk. There is a line of reasoning that diversifying will greatly reduce these risks, but in periods of uncertainty and big moves, prices fall across the board and implied volatility spikes everywhere.

Keeping the number of naked positions under control in an account may be the way to prevent a blow-up the next time the market melts down.

Defined risk vs. Naked Risk

If we compare risk of different types of option trading strategies, we can see that there is no risk-free way to trade options, and each risk level has a different set of risk parameters. Probably the closest comparison to selling naked options is to sell credit spreads.

Often, traders confuse the defined risk of credit spreads with being low-risk. In a credit spread, there is the very real risk of losing 100% of the buying power that was required or “defined” by the trade. However, during the August 5 event, the move didn’t impact most traders with out of the money put spreads, because both the long and short strikes of the trade went up significantly in value and if still out of the money, the net premium only went up a portion of the buying power as the moves mostly cancelled each other. Only when prices take an entire spread into the money are worst case scenarios in play. During the Covid crash where the market went down over 30%, this was the case for most spread traders. But on August 5, probably not.

Naked trades on the other hand have no hedge of a long option to provide any protection when the going gets tough. Naked traders are susceptible to both premium increase and buying power requirement increases at the same time when implied volatility spikes, even if the underlying price doesn’t move that far. This is the lesson for naked traders from August 5.

When the tide goes out, you find out who is swimming naked.

Warren Buffet has many famous quotes, and this is one of them. On August 5, 2024, if you were swimming naked with futures options in particular, or even naked options on margin in general, you were probably exposed. I’m not sure that this is exactly what Mr. Buffet meant by this saying, but in this case, a literal interpretation is very fitting.

One time event, or regular occurrence?

What happened on August 5, 2024 was a very unique set of circumstances that came together to create an unprecedented spike of implied volatility. Never before has VIX shot above 60 so quickly, and never before has VIX receded so quickly. So, is this rare event a once-in-a-lifetime occurrence, or will we see similar events on a regular basis?

I’m afraid that we are going to see this type of event many more times. We’ve seen global financial squeezes happen in the past, and this wasn’t even that crazy of a situation. The final straw that broke the proverbial camel’s back with this event was a liquidity crisis in Japan over a weekend. We’ve had other big banking fiascos around the world before and this one may not even be in the top 10 ugliest. What is different is the sheer amount of option positions that are in place now compared to only a few years ago. Today, it is normal for option volume to exceed the number of actual shares traded on major exchanges.

Why does the amount of option volume matter? While shareholders of stocks can simply hold through most downturns, option traders are often leveraged in fairly short duration positions that carry significant risk. When markets change, more traders need to purchase protection or need to get out of losing trades to stop their losses. If this happens when markets are closed, there isn’t much liquidity, and few sellers, so option prices go up, driving up implied volatility. With lots of people wanting to buy to get out or buy to protect, the lack of sellers can cause a panic. This is what we saw on the morning of August 5. Nothing has fundamentally changed since then, and option traders are continuing to grow in numbers.

My fear is that it will take less and less significant events to drive implied volatility and option prices to extreme levels going forward. So, if you weren’t impacted by VIX spike of August 5, consider this a warning shot across the bow. For some of us, they sunk our battleship. Don’t let it happen again.

5 Bullish Call Trades

Beginning option traders like to buy calls to start their option trading, and over time often learn the advantage of selling options and probability. But there’s a reason that long trades involving calls exist- the market goes up more than it goes down. We need strategies that use call trades to benefit from market moves up without experiencing huge amounts of time decay, or huge swings in positions. These 5 strategies provide some choices to get in on a bull market with calls.

(Without losing a lot of Theta decay)

Option buyers typically have low probability of profit because of the need to overcome Theta decay, the measure of how much option premium loses value every day. But often selling calls in a bull market is a loser as markets don’t offer much premium and go up more than expected. And the market is bullish 70-80% of the time. Are there call trades that take advantage and balance risk and opportunity better than others?

Here are five call trades that I like:

Sell a Covered Call (yes, it is actually bullish)
Buy a Long-term Deep in the Money Call (the stock replacement trade)
Buy in the money longer duration call and sell short duration out of the money call (Poor Man’s Covered Call)
Ride the up trend with an Out of the Money Call Debit Spread– double up and reset
Buy Call Back Ratio for Credit and Zero Extrinsic Back Ratio (ZEBRA) trades

Each of these trades is built for a different type of trade mentality, so it is a personal choice based on risk, time frame, and how active a trader wants to be in the market. However, with the exception of the covered call, all leverage capital and risk a total loss of premium paid but with big potential gains.

When is a good time to do these kinds of trade? Selling options is best when IV is high. Buying options is best when Implied Volatility (IV) is low and option premium is cheap. When IV is high, big moves are anticipated, but even if the market goes up, IV can contract quickly and significantly counter the gains from an up move. One overall measure to watch is the VIX volatility index. VIX has a long-term average level of 18, and when it gets in the low teens, between 12-14, it doesn’t have much lower it can go. Individual stocks can be checked for their IV level by looking at IV rank or IV percentile. When VIX is low and a stock has an IV percentile or rank below 10, I’d consider the stock IV as low. This scenario happens frequently, especially in bull markets, which occur much more of the time than bear markets. On the flip side as the market goes up and IV goes down, selling options get less lucrative and more risky.

Let’s take the five strategies one at a time. There are also detailed write-ups of each on separate pages, so this is an introduction to these trades and to contrast the risks and benefits of each before digging in deep.

Covered Call Trades

Of the five trades listed above, the Covered Call is the most conservative and the only trade that is based on a net sale of options. The trade is a combination of owning 100 shares of stock and selling a call against the shares. Because the amount of capital at risk is essentially the value of the shares of stock, which are owned in the account, this trade has no leverage from options- instead it reduces leverage and risk by adding a hedge against the shares owned.

Let’s say a trader sells a call with a Delta of 30 against their shares. The net Delta of the Covered Call position becomes 70. This means the two part position acts like 70 shares instead of 100, making the position less volatile. Since the only option involved is one that was sold, time decay always works for the call seller.

Many traders love Covered Calls because it allows them to collect premium as a source of income on shares they already own, without taking on any additional risk. For many conservative option traders, this is the one and only option trade ever needed. Depending on the underlying and tactics used, it is possible to make 5-15% income on stocks in a portfolio. Because the trade involves selling options, the probability of profit is greater than 50%, the highest probability of the five trades listed.

Covered calls improve the probability of profit over owning stock alone in exchange for giving up unlimited upside.

So, what’s not to like? It depends on your perspective, but the Covered Call limits upside gains, but does only a little to reduce downside risk. If a Covered Call owner has stock that goes up a huge amount, the call will limit how much profit can be made. The trade will be a profit, but without the call, the profit could be more. By selling a call, the Covered Call trader is collecting premium in exchange for the possibility of missing out on a big up move. On the downside, collecting premium might be a small consolation if the stock drops dramatically.

For a conservative trader, the Covered Call is a way to reduce risk compared to simply owning stock outright. For an aggressive trader, the Covered Call uses a lot of capital to get a return potentially the same as the market, with no real downside protection. I’ve come full circle as a trader myself, going from a big fan, to dis-illusioned by the lack of upside, to recognizing the benefit of a less-volatile, positive probability trade.

Stock Replacement Call Trades

The next strategy is one that is often referred to as stock replacement. With this strategy, we can buy options that have the same upside as shares of stock but at a fraction of the cost. In theory any time someone buys a call, there is the same upside as stock, but some set-ups give a trader more of the upside benefit than others.

When I think of using options in place of stock, I’m looking for two things, relatively high probability and low Theta decay. When buying a option with no hedge, the natural way to lower time decay is to buy a call well out in time where it will decay slowly. To get it to move with the underlying stock, having an in-the-money option can get most of the move up (or down).

So for this strategy, I look for options 6-12 months out with a Delta value of 75-80. These options will likely cost 10-20% of the cost of the shares as they have significant intrinsic and extrinsic value. With over 6 months until expiration, time decay is slow, but still present.

buying a long-term call in the money has almost the same profit potential as buying stock, but for a fraction of the cost. — In this example, a call is purchased with 84 days until expiration with a Delta of 0.78. Notice that even after several weeks, the profit curve is very close to that of owning stock around the money. Purchasing even longer duration options than this would provide less daily decay with even better downside protection.

Because I’m buying an option with a Delta of 75-80, I have the equivalent of 75-80 shares of stock from a price movement stand-point. If the price goes up, over time the Delta will increase and the option will behave closer and closer to the movement of 100 shares of stock.

The risk to the downside is limited to the amount paid for the options, so a big market drop could wipe out the position, but even a big drop would still likely hold some value, but mostly the extrinsic time value. However, the really good news is that losses in the options on a downturn are less than the losses that would come from 100 shares of stock.

My goal in this trade is not to hold until expiration, but to either exit or roll to a longer duration before we get into the last quarter before expiration. If the stock price has gone up, I can roll to a new time at a higher strike price and collect the amount the stock has appreciated less the time decay that was lost.

This trade needs a small move up to break even, so the theoretical probability of profit is a little less than 50%. But, by getting out way before expiration, the odds get ever closer to 50/50, and in a bull market the unlimited upside with limited downside is a pretty compelling proposition.

One watchout with this trade (and the others as well) is thinking that since we use just one fifth or one tenth of the capital of buying stock that we can now buy five or ten times as many options and really cash in. We have to respect the downside risk. A big move down will wipe out this position. So we don’t want to put all our eggs in this basket.

But when the market is frothy and looking like it is going nowhere but up, this is a good way to participate in the upside while protecting the downside, assuming that there’s plenty of capital left to deploy if the market suddenly goes against the position.

Poor Man’s Covered Call Trades

Covered calls have a number of trading advantages- they reduce volatility, provide some income, somewhat cushion a position from a fall. But, to have a covered call, you have to own stock first to sell a call against it. However, we just discussed the idea of using long calls as a substitute for stock, so if we sell a call against our stock equivalent we can have a low cost equivalent of a covered call, in other words a Poor Man’s Covered Call.

One difference is that our long calls have decay, and we want to counter that decay by selling calls with the same or more decay in our favor. A great way is to create a diagonal spread, selling calls that are closer to expiration while buying calls that are further away.

By selling a call with faster decay against our long call with slower decay, we can actually get a trade that has a greater than 50% probability of profit. The trade-off is that we limit the upside. The trade has defined risk and defined maximum profit.

My typical setup is to buy a 75 Delta call about 12 weeks out and sell a 25 Delta call about 6 weeks out, or half the time. If we look at a chart of each of the options profit potential along with how they compare to just owning stock, we get a bit of a complex chart:

The two legs of the diagonal spread that make up a Poor man's covered call. — In this chart we have two options with their own profit profiles at expiration. But, since they don’t expire at the same time, it is more important to see how they will perform at a certain point in time, like half-way to expiration for the shorter duration short call. After 21 days, the short call profit profile hugs the expiration profit profile much closer than the longer duration long call.

The key thing when looking at diagonal spread positions is that we really can’t think that much about expiration, especially for the long duration portion of the trade because it expires later. So, we really have to pay attention to how the projected values will behave at different points in time prior to expiration.

Another thing to notice is that the short call we sold has a strike price much closer to the current price than the long duration call. This means that there is more potential downside than upside, but that’s true with a regular covered call as well, actually even more so. At least our downside on this trade is limited.

When we put it all together in a chart, we can see how the trade profits not only when the market is up, but when the market is flat as well. Profitability with no underlying price change is due to the faster decay of the shorter duration short calls.

The poor man's covered call is profitable in a wide range of price movement. — Notice the 21 days in trade profit line is profitable even in a slight down move.

Looking at the overall Delta of this trade, it opens with a net Delta of 50, or the equivalent movement of 50 shares of stock. So this position is half as volatile as owning 100 shares of stock for a cost equivalent to about 7.5% of owning 100 shares.

From a profit standpoint, our capital required was $750 and the maximum profit is $250. This shows how much upside we’ve given up by selling the call, compared to unlimited upside with the call alone. However, if we look at a “sweet spot” on the profit chart above, we can see that if price goes up from 100 to 102 in 21 days, the profit is around $150, a 20% return on capital for a 2% move. In comparison, a 2% price move on the earlier long call option only would yield about a 7% return on capital, and owning stock outright would net the owner, well, obviously 2%. one way or the other, I can roll out at the same time I’m repositioning the short leg.

Is there any magic to 84 and 42 days? Not really, it’s just a time frame that I find fairly manageable without a lot of stress, but with plenty of premium to collect on the short side of the trade. Longer durations have less stress, and shorter durations are more volatile with more potential profit. It’s a choice that depends on your trading preferences and risk tolerance.

There’s a lot of ways to manage the Poor Man’s Covered Call, and I’ve written about them in an extended post.

Buying an Out of the Money Call Spread

Buying an out of the money call spread seems counter to every theoretical calculation a person can do. The probability of expiring in the money is low by definition and time decay is the enemy big time. But, over the years I noticed that when I sold call spreads that were supposed to be profitable, either alone or as part of an Iron Condor, those spreads seemed to lose money often, and often lost a lot. One thing I’ve learned in trading is that if a strategy you use continually loses, try doing the opposite. So, here we are. I’ve done a lot of back-testing and trading my own positions to come up with a low probability strategy that actually wins over time.

As I tested different variations of this strategy, it became clear that the key was to keep the amount of capital required low with lots of upside potential, but high enough that the position has a chance for success. Also, this is a trade that works best when the trade is closed for a win and not held to expiration. It also does best with low implied volatility in a bull market.

Buying a spread helps compared to buying a single out of the money call, because the sold call has similar Theta decay to the long call and counters the biggest reason for quick losses from buying calls.

With a little time and early management, this trade has a history of an actual positive average profit, even though the probability of profit from a single trade is well below 50%. Big wins can outpace a larger number of small losses. Read the detailed post about this strategy to find out the specifics to success with this trade that goes against virtually every concept I tend to advocate for.

The Call Back Ratio

In front ratio spreads, usually the goal is to sell more options than what is bought to have lots of decay protected a hedge of a long option. Front ratios are so much more common, that most people just call them ratio spreads and don’t even consider an opposite version, a back ratio.

A back ration spread involves buying more options than selling to take advantage of a big market move. With a call back ration, we may for example buy two calls and sell one call. If the market goes up, the two long calls will make more money than the short call will lose. The disadvantage is that Theta (time decay) can be a big problem. So, I have two variations of this trade that I use that somewhat counter this problem, but not completely.

A Delta neutral back ratio call spread is created by selling a call and buying two calls with exactly half the Delta of the call that was sold. The net Delta is zero, and the trade should net a credit- a trader is paid to enter the position. If both call strikes are out of the money, like when selling a 30 Delta call and buying two 15 Delta calls, it is very possible that the position will expire with everything out of the money and worthless, so the trader keeps the premium. If the market goes way up, the long calls will start to overcome the value of the short call with unlimited profit potential. Sounds great, doesn’t it? The downside is that the trade could end up with the short call in the money and the long calls out of the money worthless, so the trader is stuck with a loss quite a bit bigger than the credit received to start with.

A Delta-neutral call backspread makes money at expiration in a flat to down market or a big move up, but loses in a small move up.

An almost opposite variation flips the position of the long calls to make the trade a net debit and create the equivalent of 100 shares with zero extrinsic (time value). I picked up this concept on TastyLive.com. The Zero Extrinsic Back RAtio trade, or ZEBRA, buys two 75 Delta calls and sells one 50 Delta call for a net Delta of 100, or the equivalent of 100 shares of stock. The extrinsic value of these positions tend to cancel each other out, with twice as much time value in the short call as each of the long calls. So we get the movement of 100 shares of stock for a fraction of the cost and no extrinsic value for the position. In many ways this is a lot like the stock replacement discussed earlier.

The zero extrinsic value is a little deceptive in that the extrinsic value doesn’t decay equally. The extrinsic value of the two long calls decay faster than the extrinsic value of the short calls at the money. So, in the short term, Theta is negative, and we still need the market to move up to make money.

I discuss the ins and outs of both of these back ratio strategies in the extended post on this topic.

Conclusion

Buy an Out of the Money Call Spread

Over the years I noticed that when I sold a call spread that was supposed to be profitable, those spreads seemed to lose money often, and often lost a lot. One thing I’ve learned in trading is that if a strategy you use continually loses, try doing the opposite.

Buying an out of the money spread seems counter to every theoretical calculation a person can do. The probability of expiring in the money is low by definition and time decay is our enemy big time. But, over the years I noticed that when I sold call spreads that were supposed to be profitable, either alone or as part of an Iron Condor, those spreads seemed to lose money often, and often lost a lot. One thing I’ve learned in trading is that if a strategy you use continually loses, try doing the opposite. So, here we are. I’ve done a lot of back-testing and trading my own positions to come up with a low probability strategy that actually wins over time.

Just to be clear, this trade can be named a lot of different things. Some may choose to call it a bullish or bull call spread because it benefits from prices going up. Others may call it a debit call spread because a trader pays a debit to get into it, versus a credit spread where the trader collects a credit. So, it’s a debit spread, a bull spread, and it means we are buying one call and selling a less expensive call.

In high Implied Volatility environments, options are expensive, and it is hard to justify buying them. A big move is needed to make up for the large amount of premium paid, and time decay eats away at the position.

In low Implied Volatility environments, the cost of options is low, and strikes with fairly low deltas are often inside the Expected Move. This is much more true for calls than puts, due to skew. So, for not much cost, we can get into a position that often out performs its probabilities. And with active management we can greatly improve the long-term profit and loss.

Why buy a call spread and not just buy a single call option, you might wonder? Two reasons, cost and time decay. Buy selling a lower probability call, I can significantly reduce how much I pay for the position, but see an even bigger decrease in Theta, the Greek variable measure for daily time decay.

A key relationship to know is that the Delta values of the two options in the spread give a relative calculation of the value of the spread. The average of the Delta values taken as a percentage represent roughly the percentage of the spread width that the premium is worth. A call spread of a 30 Delta call and a 20 Delta call will have a premium value of about 25% of the width of the spread. So, if the strikes are $2 apart, the premium will be approximately 50 cents. The percentage is usually a little closer to the Delta of the higher Delta strike due to skew, but as a rough estimate, the calculation works well. Why would we care? Because if we double our Delta values, we double the value of our premium in a spread. That will be a key theme for this particular trade.

Call Spread Set Up

Here is the set up of my preferred strikes for an out of the money call spread. I try to open this trade with somewhere around 6 weeks until expiration so that time decay isn’t too bad and I have plenty of time to manage the position. Like most option trades, I choose my strikes based on Delta values. For this trade I look for a call to buy that has a Delta value in the 20s, and a call to sell with a Delta in the teens. I want the difference in Deltas to be somewhere between 10 and 15.

Let’s look at an example of a stock or ETF currently trading at $100 per share. I find that the 103 and 105 strikes meet my criteria with 42 days until expiration. The Delta values are 29 and 16, a difference of 13. The premium is 54 cents, or 27% of the $2 width between the strike prices. We are closer to 29 than to 16 as a percentage value. Our short strike has 2/3 of the Theta decay as the long, despite being less than half the premium to start, a contrasting relationship to our advantage. The net Delta of 15 also represents that we have the equivalent of 15 shares of stock, but instead of paying $1500 for them, we only pay $54.

Looking at the profit chart, most analysis of this trade by others would focus on the expiration values, and note that at expiration we need the price to rise to around 103.54 to just break even. That’s true if the trade is held to expiration. But look at the colored curve lines that represent the value at different stock prices in a week or in three weeks. Those lines don’t need much of an increase in price to be profitable, and hold decent value in a small downturn as well. These curves are the secret to succeeding consistently with this trade.

The curved lines also bear out that Delta tells us how much we make or lose based on a dollar change in the underlying stock. We should make or lose about $15 for a dollar move in the stock price, and we can see from the 35 DTE curve that this is about what we’ll get.

Finally, notice that the colored curved lines of profit and loss don’t drop very far below the starting point of zero profit at $100 stock price. This is because there is only a small amount of Theta or time decay at the beginning of the trade compared to the days that come as expiration nears. Our goal will be to avoid the times when time decay kicks in.

We also would like to act based on the part of the curve that is better before expiration than at expiration. If we hold until our position is in the money, Theta switches and moves our profit toward the maximum at expiration. But the probabilities are that we won’t see these positions go into the money and Theta will be taking money from us in ever increasing amounts every day.

Managing the Out of the Money Call Spread

Like most option trades, I like to evaluate the trade with three possible management tactics, hold, fold, or roll. Holding to expiration lowers the probability of success, but might make sense if the market jumps up shortly after entering the trade. Folding or getting out early isn’t a bad strategy to lock in gains or limit losses with this trade by using limit orders. Rolling out regularly is best if the goal is to stay in the trade for the long haul. Let’s take these one at a time in more detail.

Holding a Call Spread to Expiration

Call Spreads are an interesting contradiction in the way Theta decay works. Theta either works for the trade or against the trade, and it can switch depending on whether the trade is in the money or out of the money. Theta is driving the value of the trade toward either zero or maximum value. When we own a Call Spread, Theta works against positions out of the money, but works for positions in the money. Since this particular version of the trade starts with strikes well out of the money, we need the underlying price to go up in a substantial way to make money.

The best time environment to trade this strategy is when IV is low and markets are rising. So, a nice move up can often happen. When it does and the position is in the money, the call premium will be less than maximum profit because the two call options have different levels of extrinsic (time) value left. We can hold the position until expiration to get the last bits of decay and get maximum profit. The risk is that the price can also reverse back out of the money and make the call spread decay toward zero value. For this reason, this is a trade that I don’t like to hold to expiration, I like to get out with a big profit, either with a profitable limit order, or rolling to a longer duration while taking profit.

If the market goes down instead of up, I think it makes even less sense to hold, because the probabilities will have gone down for profit, and the remaining premium will decay even faster. A turnaround to get into the money is needed and there probably isn’t enough time. So, I’d again fold or roll.

Folding with Limits

Many traders like to use limit orders to cash out wins, or limit losses. For traders that are inclined to use limits, this call spread trade set-up has some natural places to get out. Since the upside is higher than the downside, but the probabilities are that the trade loses more often than wins, we need to make sure that wins are much bigger than the losses. One easy natural limit is to take a win when the position doubles in value, or fold for a loss when the position is cut in half. Doing this means we need win better than one out of three trades to make a profit over time on the trades that close on a limit. Let’s look at each scenario, plus the scenario of hitting neither limit.

This trade starts with a long call that has somewhere around a 25% probability of expiring in the money. But it also has about a 50% chance of a touch- the price reaches the strike price sometime before expiration. Depending on exactly which strikes we started with in our call spread, our initial premium is likely 20-25% of the width of the spread, as we discussed earlier, based on the Delta of our two strikes. That means we need the width of the spread to move up to 40-50% of the width of the spread to double in value. Getting our long strike to go in the money, even briefly, should do the trick. Are you with me on the logic and statistics here? Based on all these assumptions, we have somewhere around a 50% chance to double our money on this trade at some point before expiration. But we don’t have a 50% chance to expire in the money. So, if and when it happens, the logical thing to do would be to take the money and run.

Wait, isn’t there some old trading rule that you are supposed to let your winners run and stop your losses? If we close for doubling our money, we give up the chance to get triple or hit max profit. Yes, but with options, time is limited. Markets go up and down, and nobody knows what will happen next. When we get a big win, it makes sense to take profit before it evaporates, and then don’t look back. Usually by the time we hit double our initial premium, a lot of time has passed and there isn’t that much time left in the option, and the probability of making more is still no better than 50/50. We started with a low probability trade, and have a shot to double our money 50% of the time, let’s take that.

A couple of additional factors to consider. Theta decay increases as the trade goes on, so if we can get out early before Theta has a big impact, the big decay at the end can be avoided. Second, one assumption going into the trade in a low Implied Volatility environment is that we are in a bull market, which actually helps our chances of a win.

What about limiting the loss? If we enter a stop limit at half the premium collected, are we giving up too early? Looking at our initial Deltas and how that relates to the width of the spread, our call spread will lose half its value if our Deltas drop in half. Whether that happens due to a downturn or due to time passing, the probabilities of a winning trade or especially doubling the initial value of the trade decline significantly, and the probability of the trade expiring worthless if left alone will have increased significantly. So, the idea is to cut our losses and save some of our capital for another day. Additionally, Theta decay is only going to increase and quickly doom the trade to zero if we don’t exit.

If we enter this stop loss limit order, how often will it execute? Somewhere close to 50% of the time, maybe a little more. But we can’t have a profit limit order executing 50% of the time, and a stop loss limit order executing over 50% of the time. That would be over 100% of the time, and we haven’t even talked about a third possibility. The issue is that if we use a stop limit, some of the occurrences that we are stopped out on are situations where we would have doubled our money if we hadn’t been stopped out. So we actually reduce our odds of doubling to less than 50% with a stop loss, but not a whole lot, because to go from a 50% loss to a 100% gain would take a 4x gain from that low point, a low probability, but not zero.

Let’s look at the math. If our long call Delta falls to the 12-15 range, our chance of that strike being touched would then be 25-30%. But if that situation happened in 50% of our total occurrences, we would be giving up 12-15% of our occurrences that are destined to win, so now our doubles are 35-38% of all occurances.

There’s a third possibility with our fold strategy. We could have neither limit order execute and the trade expire somewhere between losing half and doubling. This is a fairly low probability with the two limit orders in place, because as expiration nears, the trade gets more likely to move toward max loss or max gain. To expire between the long call needs to expire in the money and the short call out of the money. And the position would have to have crept into that position and been very stable especially in the last few days to not trigger either limit order. The probability of this happening are difficult to calculate, but will be well under 10%, maybe less than 5%.

If the trade gets close to expiration and hasn’t triggered a limit, it might be a good time to consider closing early to reduce drama and hopefully collect a profit on the trade. But again, that will change the overall probabilities slightly.

With the bull market on our side, let’s assume we can double our initial premium 40% of the time, stop loss limit out 55% of the time for a 50% loss, and hold on somewhere between to expiration 5% of the time. If these probabilities held up over time, we’d average a 13% gain on this trade.

For these probabilities to play out in actual results, a trader would need to trade the same amount in dollars or in number of contracts each trade. So, set aside the winning amounts to use for making up for losing trades. It’s likely that there would be many winning trades in a row, and many losing trades in a row. Having a variable amount of cash to both compensate for losses and bank winnings would be critical.

Alternatively, letting the size of the trade double or be cut in half based on the result of each previous trade wouldn’t work. Since there are more losses than winners, the account would get cut in half more often than it doubled, and eventually be cut to essentially no value.

Thinking about this way of managing the trade over time and the implications of huge wins and huge losses, this management tactic seems pretty extreme. It provides very extreme volatility, even if a trader consistently trades the same amount of capital trade after trade. As such, this would only make sense as a very small portion of a portfolio.

Continually rolling a credit spread

If you’ve read very many other trading strategies I’ve written about, you’ll know I generally like the concept of rolling my option trades. Rolling is the concept of closing an existing trade and opening a similar trade at a later expiration and/or different strike prices. In most platforms, this can be done in a single simultaneous transaction, so that the net result is clear- is the trade collecting a credit, or paying a debit to re-position?

With a debit call spread (a spread that we are buying), we can still collect a credit to roll from one position to another. This is because we can sell a call spread that has increased in value to buy a cheaper spread that is further out of the money. If we roll to new positions over and over, and the total of our credits are more than the total of our debits, this is a winning management tactic. Both back-testing and my experience show that this tactic works for this trade most of the time, particularly in bull markets.

I like to set up a trade like we’ve used as an example earlier in this post with 42 days to expiration, and then roll after a week. After a week, time decay is relatively small, and a price move up in the underlying of a percent or two makes more than a price move down of a percent or two loses on the trade. The longer the position sits, the more time decay moves the profit curve down, requiring a bigger up move to be profitable. If the market chops up and down, the trade can eke out a profit over time. The reason is that there is much more upside than downside because of the strikes that were chosen to start the trade. But, because the underlying market is bullish, the wins should be more frequent than losers, which really makes this strategy work over time.

Let’s take an example. We buy the call spread in our example for $54 with 42 DTE. After a week the stock is up 2% and our position is worth $80, a $26 gain. We roll this trade by selling our now 35 DTE call spread for $80, and buying a new 42 DTE call spread for $54 again, but now at $2 higher strikes than the week before to have essentially the same Deltas as the position we started with a week earlier. We collect a credit of $26.

A week later, the stock goes down 1% and our call spread is worth $34, a loss of $20. We roll out to 42 DTE again, and this time pay $20 to buy more expensive strikes at $1 lower prices. Now, we have a total of $6 collected from our two rolls.

The next week, the stock jumps 3.5% and our call spread is now worth $110. We roll our position out again to 42 DTE and buy higher strikes for $54, a net credit of $56. Now, we have $62 collected.

The next week, stock drops back 4.5% to our starting price of 100 and our call spread is only worth $3. Ouch- a $51 loss! But, we roll back to 42 DTE and our original strikes paying $54, paying a $51 debit.

After 4 weeks with a stock going up and down and ending in the same place, we have collected $11 total on a $54 use of capital. That’s a 20% return on capital on a stock that didn’t move.

But, we haven’t accounted for broker commissions. At 50 cents a contract, that’s $2 each week, or $8 for 4 weeks, most of our profit. So, we might want to look for stock that has a little higher price where the commission is less of a percentage of the likely profit.

We also expect the market to trend up in a bull market, so that winning weeks outnumber losing weeks.

The advantage of rolling and staying well away from expiration is that we avoid the rapid decay near expiration and we achieve much of the same result as the previous “folding” limit management tactic with constant trade size, but in a more disciplined drum-beat approach. We aren’t tempted to bump up our trade size or cut it way down, because we are just rolling the same number of contracts out week after week, adding or subtracting cash as we go.

From a practical standpoint, each week we have to evaluate what the right strikes to choose are. I try to maintain the same width, but then look for Delta values that meet my criteria. The higher the strike prices, the further out of the money the strikes are, and the lower the cost and the lower the Deltas. I can maneuver around a little to make my new position cheaper than the one I’m closing and collect a credit.

Also, if we have a big move in less than a week, I may choose to roll up my strikes in the same expiration to bank my profit and limit the downside in case of a reversal. In our example, if the stock price went up $4 in a couple of days, I’d roll up my strikes $4 and collect $65 to get my Deltas back to the starting range.

Why this Delta range works

Delta is a very handy measure for options. And for this call spread trade, its many uses really illustrate how this trade works. For call spread, we can take the combination of the Delta value of the two call options to get a net Delta value. In this example, with Deltas of 29 and -16, the net Delta is 13. (Call Deltas are positive. Owning a call is positive Delta, being short is negative Delta.)

If we look at Delta’s definition as a relation of change in price of the stock to change in price of the call spread, we can see that if the stock goes up $1 in price, our call spread premium goes up 13 cents, or $13 for the full contract. As a representation of equivalent stock, 13 Delta means we have the equivalent of 13 shares of stock.

Now, we could have this same price movement and share equivalent with any number of call strike price combinations. We could have bought a 50 Delta and sold a 37 Delta, or bought a 93 Delta and sold an 80 Delta and had the same behavior. 13 Delta is 13 Delta. So, what is the difference?

Remember, Delta is also a measure of probability and value of a spread. Both of these are tied to the individual Deltas more than the net Delta. Probability informs us of what is likely to happen to each option if held to expiration, or how likely it is that the stock price will touch the strike price before expiration. These probabilities inform our management of the option, as we’ve discussed earlier in this write-up. If we chose different strikes, we’d probably want to consider management tactics differently to optimize the trade.

But the real key is the relationship of Delta as a measurement of the value of the spread. Earlier, we mentioned that the average Delta of the two options in a spread roughly approximates the premium when calculated as a percentage of the width of the spread. Sounds complicated, but not really. In our example, our strikes are 103 and 105- the width of the spread is 2. The average of our Deltas is 23.5, so we should expect premium to be around 47 cents (23.5% of $2)- it’s actually 54 cents, but close enough for a rough estimate.

The value of our call spread can vary anywhere from 0 to $2 by expiration, so there is a lot further to go up than to go down. Picking lower delta strikes limits our downside, but gives us lots of upside. That plays out over time with this trade, as long as we don’t plan on holding on too long.

If we chose strikes deep in the money, we’d be virtually guaranteed to expire in the money, but our profit potential would be very limited, while our potential loss would be high. I think there are better ways to use deep in the money calls like a stock substitution strategy using calls, or a poor man’s covered call.

At the beginning of this writing, I mentioned how initially I used to sell call spreads, but realized I was consistently losing money. I looked at a lot of different ways to trade the opposite, to buy call spreads instead of selling. One tool I use for analysis is back-testing. As commercials like to say, “past results is no guarantee of future earnings,” but with big samples back-tests can provide a clue as to what works more often than not. I back-tested a wide variety of call spread values at different Deltas, different expirations, different management strategies, and different market environments before settling on this variation. I’ve traded it a lot myself with good results.

The example I’ve used in this writing is a little closer to the money than I’d ideally prefer. A little further out of the money would get the premium more around 20% of the width, which would cost less to start. The net Delta is fine, but if there were more choices, I might make is slightly less. Wider spreads are good for selling spreads, narrower is better for buying spreads, due to Theta differences.

Can we get too far out of the money, or too narrow? Yes, at some point the premium we pay and the potential profits get too small compared to the commissions and fees required. So, small spreads on cheap stocks may not make enough to pay for trading costs. And for those that might get options trades for free or close to free, there is still the cost of bad fills if an option is not extremely liquid.

This isn’t to say that other variations won’t work. There are pros and cons to every element of this trade. The differences in returns and risk can be adjusted many different ways. I’ve tried to illustrate the trade-offs so each trader can make their own informed choice.

Assignment Risk

One factor we haven’t discussed yet for buying call spreads that can’t be ignored is the risk of having a short call exercised while still holding the long call. As with other strategies that have an element of selling calls, there are some call assignments that can be avoided and some that can’t.

There are three situations that greatly increase the chance of a short call being exercised by the buyer. They are having a call in the money, having a call near expiration, and being short a call when a stock goes ex-dividend. The good news is that the way I execute this trade, these factors should rarely come into play.

First off, the short call is much less likely to end up in the money than the long call. If we start by selling a call with less than 20 Delta, it has less than a 40% chance of having the stock even touch its strike price.

My plan is never to hold until expiration, so that part of the assignment risk is mostly avoided. For those who hold in the money spreads near expiration to try and get max profit, this is a double dare to the buyer of the trader’s short call to exercise early. So, someone who holds a winning trade until expiration shouldn’t be surprised to wake up short 100 shares of stock instead of being short a call option.

Dividend risk is probably the hardest call exercise to avoid, but the key is to have a short call with more extrinsic or time value than the anticipated dividend, and have strikes further out of the money than the dividend. If a trader can do that, there is no reason for a call owner to execute from the other side of the trade. The easiest way to keep a high extrinsic value lines up with the other tactics- get out of positions close to the money and keep expiration away by closing or rolling anything with short duration.

As I’ve explained in other write-ups, having a short option assigned/exercised isn’t that big of a deal to undo, especially when it is part of a spread. A trader may wake up and find a large amount of short stock and a large amount of cash that wasn’t in the account the day before, but that’s what happens when shares that you don’t have get called away. In this case, the intrinsic/in-the-money portion of the long call will always be worth more than the intrinsic value of the short call, so the long call can be sold and the short shares that were assigned can be bought back, all in one transaction, for a tidy overall profit.

Final Thoughts

Buying a call spread like the trade discussed here should not be the core of a portfolio- the trade is simply too volatile for anything other than a way to supplement returns in appropriate market conditions. But, as used as a part of broader portfolio of trades, it can be a way to take advantage of a bullish market with low Implied Volatility. Buying calls out of the money doesn’t have to include a lot of decay. Using a spread reduces the time decay and makes what would seem like a losing trade show profits over the long haul.

Underlying Security vs Risk Permission

What level of option risk goes best with what type of underlying security? Depending on the option strategy, your choice of underlying security type can have a big impact on your outcomes.

What level of option risk goes best with what type of underlying security? Most people reading this might wonder what in the world is the point of this topic and why should I care? Depending on the option strategy, your choice of underlying security type can have a big impact on your outcomes. This might get a little deep, but hang with me and I think it will be worth your time.

4 risk levels, 4 underlying types

Brokers typical allow customers to trade options at four different levels of risk. I’ve written about how the risk compares between these levels. As a reminder the four levels are:

Level 0: Covered options- cash secured puts and covered calls
Level 1: Buy options
Level 2: Option spread trades- buy an option, sell an option
Level 3: Naked option selling

There are also four general types of underlying securities for trading options. With each comes different advantages and disadvantages. As a reminder the four types are:

Individual Stocks of Companies
Exchange Traded Funds (ETFs)
Index Options
Futures

For example, there are three different classes of underlying securities for trading options on the S&P 500 index: ETF options like SPY, Index options like $SPX, and Futures options like /ES.

So the question and point of this post is to examine which risk permission levels work best with which types of underlyings. It’s not an obvious question or an obvious answer. Most traders would say it doesn’t really matter- more risk is more risk, and less risk is less risk. But some underlyings are better built for certain strategies more than others. It doesn’t mean you can’t trade a strategy for a certain underlying, it is more of a question of what is optimal for the type of risk and potential return you are seeking in a trade.

The Matrix

I made a sixteen square matrix to evaluate each combination. I rated each pairing based on how well the option risk matched with the characteristics of the underlying. My conclusions are simply my opinions, and I welcome discussion and other opinions backed by data. So here is my matrix and what follows is the data and logic behind it.

underlying security vs option risk levels — Some types of option strategies and risk are better suited for certain underlying securities than others. With each combination is a brief explanation. Green choices are best.

Let’s review the boxes one row at a time, by risk level.

Covered Options

Covered or secured option strategies include covered calls, cash secured puts, covered strangles, and the wheel strategy. These strategies use the full value of underlying shares either in cash or shares to protect against loss from selling short options. The options being sold are much less volatile than the value of shares, so covered options are the only option choice that is a clear reduction in risk compared to owning shares outright. All versions of this option trading strategy limit upside growth while allowing the potential of losses to zero, but most of the time these strategies outperform owning stock outright. So how does this type of transaction impact different underlyings?

Individual stocks can be very volatile. Positive or negative news about earnings or products or lawsuits or mergers or management changes can make stocks move way outside their expected moves. These outsized moves happen more often than normal statistical distributions would predict. Even so, individual stocks tend to have options with much higher implied volatility than the overall market. For stock investors that want to dampen day to day moves of their portfolio balances, selling secured or covered options is a great way to participate in individual stocks with less drama. Because of the crazy volatility of individual stocks and the high implied volatility of options on individual stocks, covered options are a great match for individual stocks.

I would argue that for both the covered strategy and the stock underlying type, this is the strongest match in this row and column. There is no better underlying for covered options than individual stock, and there is no better option risk level for individual stock. I know a lot of people will disagree, but as we look at the other combinations, I hope you’ll at least understand my point of view.

Covered options on exchange traded funds are fine trades. It’s probably the safest possible option strategy there is if we want to call any kind of trading “safe.” We combine a bunch of volatile stocks together into a product that dampens volatility down substantially. Then we sell options against that new product that will rarely see moves outside the moves that are expected. The options may not pay a lot, but they won’t lose often either. A very boring way to make steady gains (and I’m thinking of boring as a good word here).

An argument could be made that covered options on ETFs is perfect for both, because it’s a double volatility reduction, and for risk-averse traders that’s a great combination. I get that, but for me, I think it’s a little too much volatility reduction, and sacrifices too much option premium for safety. Be less volatile with stocks by selling covered options, or be less volatile with riskier option strategies by using ETFs, not both. But I’m generally a risk taker, so maybe I under-appreciate the double volatility reduction of covered option strategies with ETFs.

Covered options on indexes is the easiest combination to rate on the matrix, because it is the one combination that can’t be done. We can’t own an index outright, so we can’t sell a covered call. If we sell a put and get assigned we don’t get the index, we just pay up the cash we lost. So, there isn’t a real way to sell covered index options on the underlying index. This is the only red square in the matrix because it can’t be done.

Covered options on futures can be done, but it doesn’t really make sense. Futures and futures options are all governed by span margin, so really there isn’t an official way to sell covered options on futures, because there is margin being used on every leg of the trade. No piece is fully “covered.”

I almost made the covered futures options block red, but you can kind of do it if you set aside the cash that the full notional value of the future is worth when you sell a call against a future, or sell a put on a futures contract. The problem is that your buying power won’t show that you’ve locked up the full notional value, so you have to track it yourself. It just isn’t what futures are about.

Let’s do a quick example to illustrate. Let’s say we have a futures product that trades for $1000 with a multiplier of 50. So the notional value of a contract is $50,000. If we buy a futures contract, the broker will use SPAN margin and only take away at most $10,000 of our buying power, even though we are on the hook for the full $50,000. If we sell a call on the same future, we’ll likely gain buying power, as we just reduced the volatility of the position. Maybe SPAN margin says we now only need $5,000 buying power, while we remain at risk for $50,000. So, our broker and SPAN margin don’t make us “cover” our options. You can keep $50,000 in your account to cover the trade yourself, but nothing forces you to, other than wanting to eliminate any risk of blowing up your account in a downturn. It’s fine to do this, but it technically isn’t a covered option, so it’s a yellow square on my matrix.

Buying options

When most people first learn about options, buying an option is the trade they can easily understand. You pay a premium to have the option to either buy or sell something. Margin is not a factor, because the risk is defined. The risk of the option is the cost, it can end up worthless, a total loss, but no more than what was paid to own the option. If the option ends up in the money, it may be profitable, maybe very profitable. Leverage comes from the possibility of virtually unlimited profit for a relatively low cost.

Buying puts or calls is like going to the security market casino. It’s a low probability bet that might pay off big, but often will lose what you gambled. But let’s not get all “judgy” against the strategy- lots of directional traders buy options to get the most out of a move they think will come. When implied volatility is low and the market is rolling up nice gains, it can be a very lucrative trade that exceeds its predicted probability. But which underlying security types are best fit to take advantage?

Individual stocks can make big moves up or down, and owning an option in the right direction when a big move happens can be great! But the market knows that individual stocks are prone to big moves so options are expensive to buy. A little move won’t cut it. A trader has to be very right on timing and direction.

But, if buying calls or puts is your thing, the biggest rewards are with individual stocks. So, I’ll give it a green square.

Buying options on ETFs is cheaper than stocks, but the likely moves won’t be as big. However, if the goal is to ride a trend that is going up faster than what implied volatility predicts or a slide going down, ETF long options are a good choice.

In a bull market, selling calls is usually a loser, which means that buying calls can be a winner. Buying calls on an ETF in a bull market will hit a lot of winners usually without a lot of capital required, so probably the best use of the strategy in this row.

Buying put and call index options is a very similar situation as options on ETFs. It’s really a matter of preference, depending on several factors. Some brokers restrict access to index options, so it might not even be a choice for some accounts. Most index options are bigger notional value, often 10 times as big as the equivalent ETF, so it might make more sense for a bigger account to use index options, while smaller accounts stick to ETFs. There are a lot more ETFs available than index options, so niche indexes either don’t have an index option or have such poor liquidity that the only choice is an ETF. Commissions per contract are often higher on index options, but per notional amount are lower. So, it depends on a lot of things. I’ve discussed the differences in much more detail in my write-up of different ways to trade the S&P 500. All the same trade-offs are true for the Nasdaq 100 and Russell 2000. So, for some traders buying options, the index option might be best so I’m coloring the combination green, but for most traders smaller, more liquid ETFs are going to be a better choice.

For futures options, the issues are similar as comparing index options to ETF options, except that buying futures options outright negates much of the advantages of futures options, but keeps the negatives. Futures options are a favorite of experienced and sophisticated traders because they can be traded with lower SPAN margin requirements, giving a trader more leverage, and also letting opposing positions reduce buying power. But, if a trader is only buying options, buying future options doesn’t gain much in buying power, but will cost a lot more in commissions and slippage from lesser liquidity than ETFs or index options. In my opinion the only time it makes sense to buy a futures option is to counter a bunch of short futures options or other futures position. I talked about this in my discussion of buying the 1 DTE straddle with futures options.

In the end, unless you have a really good reason to buy options on futures, it generally is a better trade to buy a similar ETF or index option product. So that’s why I colored this combination yellow.

Trading Option Spreads

Let’s define an option spread as buying and selling an equal number of puts or calls. There are a lot of ways to trade spreads, and many of my favorite strategies fall in this broad risk category. Option spreads have defined risk, but as strategies get more complex, understanding exactly how much risk a trade has defined can get a little tricky. It isn’t as obvious as the risk with buying an option, but the risk is known.

We can think of spreads in two main categories, debit and credit spreads. Debit spreads are trades where a trader pays to enter the trade, and credit spreads pay the trader to enter the trade. Credit spreads are often the highest leverage version of selling options, with the highest potential return on capital for many positions. With that potential high return on capital comes the risk of a total loss, often many times the amount that was collected to open the trade. How do these factors impact different underlyings?

With individual stocks having more likelihood of an outsized move, there is a bigger chance of a total loss on a credit spread, although that is somewhat balanced by higher premium from higher implied volatility. Debit spreads tend to limit max gain in exchange for improved probabilities compared to buying options outright. So, debit spreads on a individual stock miss out on big gains without a outsized increase in probability of profit.

Many traders favor spreads for individual stocks over naked options because of the defined risk limiting losses to a defined amount. My view is that both strategies have to contend with outsized moves and it’s a matter of picking which poison does the least damage. But because so many like spreads as a risk reduction for individual stock options and it is a viable strategy, I’ll rate this combination a yellow.

I’m going to lump ETF options and index options together for spreads. Just like with the earlier discussion on buying options, the difference between ETFs and indexes is a matter of preference and an individual’s account situations. Strategically, I like both for buying and selling spreads. Because ETFs and indexes are made up of many stocks, they have much fewer out-sized moves than individual stocks. This makes the leverage of spread trading work well, both in credit and debit type spreads.

In particular, selling put spreads on ETFs and indexes can be a high probability trade. I’ve written about this my page on selling put spreads. I’ve also written about the best delta for put spreads, and the best deltas for rolling put spreads. And in each case, I tend to stick to some version of a put spread on the S&P 500. I’ll add a call spread to turn the trade into an Iron Condor, which I’ve discussed in my post on rolling Iron Condors.

As for buying spreads, I’ll occasionally buy a call spread when the market is particularly bullish and Implied Volatility is low. Buying options in any style is usually a low probability trade, but there are ways to improve odds, and using a spread to have decay on the short leg off-setting the decay being lost on the long leg can be a big help. We can get more exotic with diagonal trades selling a nearer term option while buying a longer term option and actually having positive Theta for our trouble. In all these trades I like ETFs and indexes because the results tend to be more consistent.

Many of the ratio type trades that I do utilize two sets of spreads, like the popular broken wing butterfly trade. Again, I like ETFs and indexes because outsized moves are less likely than individual stocks.

You may be sensing a theme. Less outsized moves make using the highly leveraged option spread on ETFs and indexes my favorite choice for spread trades. It’s green squares for both, and my favorite use of ETFs and indexes, as well as my favorite way to trade spreads.

In theory, futures option trades with spreads should also be as favorable as ETFs and indexes. They work about the same and have the same type of probabilities. But there are two things that I don’t like about trading spreads on futures. One is a personal nit-picky concern, and one is a concern that virtually any trader would have.

Let’s start with the most legitimate concern. Futures options are less liquid than ETF and index options. They have wider bid-ask spreads, and they are harder to fill close to the mid price between the bid and ask. In many trades, the tick size, or the amount you can adjust your limit price by is substantially bigger than for the same trade on an index option on the same thing. For example, on $SPX index, we can adjust our limit orders by 5 cents up or down, but with /ES futures, we have to adjust our order in increments of 25 cents. To make it worse, often the volumes are much lower and even giving up 25 cents won’t get an order filled. So, it can cost a lot to get filled, and we haven’t even talked about commissions, which are generally also higher, both per contract, and even more so as percentage of the notional value of the position. Maybe someday these costs will get lower and it won’t bother me as much, but I just don’t like it for spreads with futures options.

But what about SPAN margin you might ask? Doesn’t that extra margin make it palatable to pay a little more so you can get that super-duper leverage for traders that like more risk and more reward? Well, this is my nit-picky problem with spreads on futures. SPAN margin isn’t that much extra buying power for spreads with futures options compared to indexes, ETFs, and individual stocks. Because spreads have defined risk, the two sides of the trade already have formed a hedge and SPAN margin doesn’t give much more buying power than the reduction from calculating the max loss of the total spread being wiped out. To be fair, futures traders get some additional buying power, but it isn’t enough for me to justify the higher costs of trading spreads with futures options.

I know there are traders out there that like futures with spreads that little extra buying power that comes from SPAN margin, but for me it makes more sense to go with an index option or ETF option where my risk is defined and doesn’t change. So, I’m giving this spot on the matrix a yellow. Proceed with caution.

Selling Naked Options

Selling naked options is supposed to be the riskiest of the whole bunch of risky option trades. In one way it is in that maximum losses are essentially undefined, but even with margin, the leverage of Theta or Delta as a percentage of buying power is often less than what happens with spreads. So, as long as we avoid outsized moves (which we can’t, by the way) there’s a strong argument that selling naked options is not nearly as risky as it would seem at first glance.

Let’s be clear about what selling a naked option is about. With covered options, we can sell a call or a put and there is either cash or shares covering the short option positions. For naked trades, the broker lets us sell on margin. Often we are only required to have something like 20% of the notional value set aside for covering the option sale. That’s great for our account as long as the price doesn’t move against us more than that 20%. Actually, the broker will increase buying power requirements as price moves against a position, so the requirements are always in flux. But with plenty of extra cash as a buffer and markets not going crazy, it’s manageable.

So, we are selling options on margin. What underlying type does this work best with? Let’s check out our four choices.

Individual stocks are the most likely underlying to have an outsized move, so they are the most likely to get a naked option trade into trouble. It doesn’t take much, a change at CEO, a merger or acquisition, surprising earnings announcements, good or bad product news- any of these can trigger a move way beyond the expected move. With individual stocks, the probability of an outsized move both up or down tends to be greater that what Delta would predict, or it often just isn’t that great compared to the other products with diversified components.

That’s my reason for avoiding naked options on individual stocks. I know lots of people trade naked options on stocks all the time, diversifying their holdings to reduce overall risk. But for me, why not use an underlying that is already diversified? I know individual stocks have higher Implied Volatility to pay a seller to take on that added tail risk, but for me it just isn’t enough. I’ve seen too many situations where a trader has gotten a very nasty surprise and lost way more than they thought they could. It can happen with any naked trade, but it’s more likely with individual stock options. So, for me this is a yellow box- proceed with extreme caution.

Now, let’s not try to make the argument that naked options on the other types of underlyings are super safe. They aren’t, and you can lose big. Ask anyone who had naked puts on the S&P 500 (any version) when Covid hit in 2020. It was bad. But those kinds of moves happen much less often than negative moves in individual stocks. People that trade naked options take a lot of risk, and so the question for the remaining three underlying types isn’t which one is least risky, but which gives you the biggest bang for the buck? If you are selling naked options, you better know what the risk is, but how do you maximize return when you have a trade go your way?

Like the last two levels of risk, ETFs and index options have essentially the same pros and cons for naked options. While there is significant tail risk, it isn’t as high as individual stocks. So, naked options sales on ETFs and indexes tend to perform better than the expected move would predict. This makes these underlyings a better choice for underlyings on naked options. As a result, I’m giving these matrix squares a green rating.

Finally, we have selling naked futures options. On one hand this is a highly leveraged trade with ultimate tail risk due to SPAN margining. On the other hand, this combination gives a trader the potential for significant high returns on high probability trades that otherwise might not make sense.

I look at naked futures options as the ultimate “go big or go home” trade. If a trader wants to trade futures options, selling naked gives the ultimate amount of exposure for the least buying power. SPAN margin allows a trader to use a fairly small amount of capital to open a naked trade. And if a trader balances the Delta of both sides of a trade, buying power requirements become even less, as the total risk is considered in required capital.

SPAN margin also lets a trader have different sides of the trade be at different expirations and have the net exposure of each side be considered in the SPAN margin calculation. The point is that for the most agressive, risk-tolerant option trader, there is no higher leverage way to sell options than selling naked options on futures. For that reason, I really like futures for naked options.

Selling futures options naked still have the issue of poor liquidity and higher commissions, but the flexibility of SPAN margin finally makes it worth the cost for risk-tolerant traders. It is worth noting that the liquidity and commissions are significantly more of an issue for traders that trade “micro” versions of futures options, like /MES, compared to /ES. Whether it is a futures product on an stock index, a commodity, or a currency, the micro versions just have a lot less open interest and liquidity. So, if account size limits trades to micro futures, a trader has to watch which expirations and strikes can be entered and exited without huge price slippage, particularly when exiting early.

Despite the cost issues with futures options, selling naked futures is my favorite use of futures options, and my favorite way to sell options naked. I give it a green box on the matrix. I don’t rate it this way to suggest it is a safe trade, but that it is the ultimate use of options leverage.

Bonus sections

There are a few option strategies that don’t fit neatly into the four categories of risk that I think deserve a special mention because I talk about them in other parts of the site.

Bonus #1 Ratio Style Trades

Ratio style trades are a more complicated type of strategy where there is an unbalanced number of contracts sold vs bought- a lot of times a 2:1 ratio in some variation. If there are more contracts sold than bought, the trade becomes a level 3 naked trade, like the 1:1:1 or 1:1:2 put ratio trade that I discussed in other pages. But often, I use a level 2 defined risk version of the trade by adding long options to equal out the short options, usually creating a wide credit spread along with a narrow debit spread, like a broken wing butterfly (1:2:1), broken wing put condor (1:1:1:1), or 1:1:2:2 put ratio.

These trades are technically either a group of spreads (level 2), or a spread with a naked short option (level 3), but is there a difference in what underlyings are best for these kinds of trades because of the ratios and odd ways of managing these types of trades? The short answer is not really.

For level 2 defined risk ratio trades like butterflies, condors, and 1:1:2:2 trades, I like ETF and index options for their liquidity and reduced volatility. This is the same logic as with spread trades in general.

For level 3 naked versions of ratio trades where there are more short options than long, my preferred underlying is futures options due to the reduced buying power of SPAN margin. These trades tend to be fairly highly probability of profit, but with significant tail risk from black swan type events. SPAN margin considers this risk and allows a trader to use a fairly small amount of capital to enter this kind of trade. Anyone trading this way must consider the significant tail risk into their management strategy.

A trader can use ETF or index options for these naked ratio trades, but they consume a lot of capital with standard option margining. Traders with portfolio margin accounts might find this more acceptable. For understanding of different types of margin in options, see my post on the topic.

Bonus #2: 0 DTE trades

0 DTE trades have special considerations because of their short time frame. Let’s throw in 1 DTE and any options trade that has just a few days until expiration. All these trades focus on either last minute moves or the extreme decay that comes in the final days or hours of an option contract.

Individual stock options don’t have daily expirations, so expiration day trades are usually limited to Fridays or end of month at most. That essentially eliminates them as a candidate, but it gets worse.

With options near expiration, assignment at expiration or near expiration is a big concern. Individual stock options and ETFs in the money can be unexpectedly assigned into shares in the days before the options expire. And if options are held to the end of the expiration day, assignment can happen even if the market closes with options out of the money. A late after the market news event could trigger option holders to exercise their options on individual and ETF options, so you never know.

So, that leaves index and futures options. Index options are settled to cash at the market close. Futures options expire into futures contracts at the market close. A trader doesn’t have to worry about after market events impacting an expired position. The only exception to this is monthly index options that settle on the open of the market, but stop trading at the market close of the previous day. These contracts have AM expiration, where almost all other options expire in the PM, at the market close. The ticker symbols for index options expiring and settling at the market close generally end with a “W” for weekly, which originally was for the weekly expirations that happened every week, but now happen every day. The monthly options, which are the very original index options, don’t have a “W” at the end of their ticker indication.

Settling to cash vs settling to futures contracts or shares is a big difference. Most expiration day traders don’t want to deal with the underlying securities ending up in their account and the significant notional value that comes with them. Because of that, index options are far better choices for trades approaching expiration.

Traders with small accounts can choose between micro index options, like $XSP, micro futures options like /MES, or ETFs like SPY. They have different pros and cons. Micro index options have fairly poor liquidity with wide bid/ask spreads and big tick sizes for poor fills, but settle to cash at expiration. Micro futures options have worse liquidity and bid/ask spreads, plus high commissions, and settle to futures contracts, all negatives, but are usually half the notional size of the other two low capital choices. ETF options tend to have good liquidity, but settle to shares at expiration, or after expiration. None of these are ideal, but if a trader wants a small option stake on expiration day, these are the choices to consider.

Conclusion

So, there you have it. A fairly exhaustive analysis of the various combinations of trade types vs underlying security types. Some of the factors I consider most important in this analysis, may be less important to other traders, and some accounts at certain brokers may not even give a trader a choice to have some of these types of underlyings available. Others may not have some risk permissions available.

In any case, my hope is that whatever level of risk or underlyings a trader has available, it is clear what combinations make might more sense from a viewpoint of risk, potential reward, capital usage, and trading costs.

Trading Options with a Full Time Job?

Most people have full time jobs. Can someone manage an options portfolio and work full-time without watching the market all day? I say yes.

Most people have full time jobs that don’t involve the financial markets. Can someone manage an options portfolio and work full-time without watching the market all day? I say yes, and they may do even better than a full time trader. The reasons may surprise you.

For several years I was a full time options trader, watching positions in a bunch of accounts, adjusting every day as the markets moved. Many of my positions were short duration, which meant that I needed to stay on top of them. Much of my strategy involved rolling to avoid getting to expiration or to keep my strikes out of the money. There were lots of good reasons to spend the day reviewing every position in every account to determine if any adjustments were needed. And I enjoyed it. It was fun managing accounts that were growing and generating the income I needed.

But in 2022, I had a series of events that drained my accounts that provided my spending money. (Separately, I’ve written about my lessons learned in 2022.) I’m not yet to the age where I can take money out of my retirement accounts without penalty, and I didn’t want to get into Substantially Equal Payment Plans (SEPP) to commit to withdrawls- that’s a big topic for another day in itself. The bear market coincided with some unexpected expenses, so I liquidated most of the liquid accounts I had available at bad times. My accounts that had been providing nice streams of income lost a lot of value when I needed them most. So as the year came to a close, it was clear I needed to get a “real” job again.

Changing to a full time “real” job

In January of 2023 I started working full-time, a typical 9-to-5 job. But I still had a number of accounts to manage, a combination of retirement accounts and leftovers from my cash/margin accounts that I hadn’t completely used up. (I didn’t go broke, I just wasn’t flush enough to live off my accounts that I could draw from.) I had to have a different approach to account management- the days of full-time trading were over.

I still wanted much of my portfolio to be option-based. I’ve seen how options give me leverage and the ability to manage in any type of environment. But I knew that my approach to managing daily had to dramatically change. I couldn’t watch the market and do my job, so I needed to completely change my trading routine.

First, I decided to stop all 1 DTE and 0 DTE trades. Honestly, these had not been that profitable and were the most time-consuming positions I had been trading. It was almost like I had been trading them to keep my day completely filled with activity. If you read about my 1 DTE Straddle management approach, you’ll see that I try to take profit and adjust positions throughout the day, which is very time-consuming. 0 DTE trades are just as time-consuming for most strategies. I know some traders open a position and set up stop and profit limit orders and go about their day, but even that seemed like more than I wanted to do. So, no more expiring option trades.

Next, I moved all my shorter duration trades out in time. I was doing some 7 DTE put spreads, rolling almost every day. These were problematic in the 2022 bear market anyway, so it wasn’t a hard decision to get rid of them. I also decided to mostly stop doing 21-day broken butterfly trades. This was a harder decision, as I’ve had good success with defending these even in tough times, but I knew that I just didn’t want that responsibility to keep an eye on them.

So, I was left with positions mostly 4-7 weeks from expiration- put spreads, iron condors, covered calls, covered strangles, some 1-1-2 ratios, and some long duration futures strangles. All these trades are far enough out in time that a move during the day won’t be a huge loss or need an immediate adjustment.

Initially I thought I’d try to spend a half hour each morning when the market opened before I started my job. For a few weeks I did this, but I found that my work often required me to be available for an early call during that time, or there were urgent items that couldn’t be delayed, and that time wasn’t available. I’d miss a day, then it was two or three in a row, and I realized I needed to be able to have an approach that could go several days at a time without requiring action. But, I also noticed that missing several days wasn’t hurting my market results, especially in a choppy market.

Since almost all my trades are based on profiting from premium decay, time is my friend. I need time to pass and the market to remain somewhat stable. Getting away from the daily noise of the market up for some reason one day and down the next for another reason helped remind me that selling options is about being patient. It also reminded me that market movements are mostly noise that is statically insignificant. If I don’t react to every move, the market tends to chop up and down and not really move that much or that fast over time, which is exactly what a seller of options needs.

My new routine

With time, I’ve settled into a trading routine of doing a thorough review of all my positions about once a week. For positions in the 4-7 week to expiration window, I like to roll and adjust Delta about once a week, essentially kicking the can down the road, trying to pick up a percent or two of return on capital each time. Timing isn’t critical, but I want to keep my spreads in the sweet spot where they decay the most, with short strike’s Deltas in the high teens to low twenties. I’ve written about this in many posts that address best Deltas for put spreads.or for rolling put spreads. I’m leaving a bit of money on the table, missing the very best timing, but I’m making up for that by not over trading, which I clearly was in 2022.

Some of my longer duration trades, that are 2-4 months out, can go weeks or even a month or more without an adjustment roll. My weekly checks just make sure that they are not getting close to being tested or getting to a duration that I want to extend. My philosophy with those positions is an “if it ain’t broke, don’t fix it” approach. So, not much to do with these.

So, it takes me about an hour a week to make adjustments during market hours. I find a break in my day, or a day when I can get trades in early before my work day starts. I’ve been surprised at how manageable it all is. I’ve realized that when the day comes that I don’t need a job anymore, I will be able to manage my trades with a lot less time than I was using the last several years. I don’t plan to ever trade all day long again.

Results

The great news is that I’m very happy with my results. My most aggressive accounts have been pulling in about 10% returns each month so far in 2023, and all my accounts are handily beating the market. So, I’m very happy with my new approach. I know that the market isn’t always this calm, but I also know from 2022’s bear market that longer duration trades in high volatility have much better outcomes than short duration trades, so I’m confident that this approach would have done well in that environment, better than I did trading every day with short duration trades.

0 DTE Option Trading

Many people are buying and selling options with zero days to expiration (0 DTE in option lingo). But is this a good idea? Are there strategies that actually work? Or is this just gambling? Well, like many things in options, it depends. There are strategies that have been successful with years of history, and we’ll dig in to discuss them.

In 2022, the option exchanges rolled out options on a few indexes that expire every day of the trading week. This has caused a frenzy of option trading by individuals who are trading a variety of expiration day strategies every day. Many people are buying and selling options with zero days to expiration (0 DTE in option lingo). But is this a good idea? Are there strategies that actually work? Or is this just gambling? Well, like many things in options, it depends. There are strategies that have been successful with years of history, and we’ll dig in to discuss them.

Over the past several years, the frequency of option expirations has increased dramatically, particularly for the major indexes, the S&P 500, the Nasdaq 100, and the Russell 2000. Initially, there were only monthly expirations that expired on the third Friday of the month. Options expiring every Friday were added several years ago, and Monday and Wednesday were added a few years back, and finally in 2022, Tuesday and Thursday expirations were added. Trading volume has grown exponentially, and trading on options expiring within the next few days are now the majority of option trades. Clearly, expiration day trading is very popular.

I’ve been exploring trading strategies for expiration day for several years, going back to when we started having expirations available for Monday, Wednesday, and Friday. I’ve discovered that 0 DTE is not for everyone, can have many elements of gambling for many, but has a few strategies that have a positive expectancy of profit.

Things to know about 0 DTE

First off, 0 DTE requires a different mindset than longer duration trading. Profits and losses explode in minutes, making the importance of having a plan critical. Options in general require strategies and planning, but 0 DTE is significantly more volatile. So, for traders that can’t handle huge swings in value over very short periods, 0 DTE may not be a good place to go.

For traders that do trade 0 DTE, I highly recommend keeping a log of all trades to be able to evaluate whether the strategy being used is actually working. Some trades have fairly high win rates, but have big losses when they lose- a log will help a trader determine if the wins outweigh the losses over the long run. Also, keeping note of what went well and what went wrong will help a trader learn from success and failure. I can tell you that most traders that fail do so by not sticking to their own rules for managing risk.

One key consideration is the Pattern Day Trade Rule that applies to accounts with less than $25,000. Federal regulations prevent small accounts from opening and closing the same position the same day more than three times in any 7 day period. Doing so will place severe limits on the traders account. If you have an account with $25,000 or less, or even just slightly more, you need to be very aware of this rule and how it works before even thinking about 0 DTE trading or any short duration in and out trading strategies.

There are a number of ways to trade 0 DTE. Some traders try to get in and out, while others hold a trade to expiration at the close of the day. Some are net buyers of options, what I will call debit trades, while other are net sellers, or credit traders. I say “net” because many strategies involve trading spreads, buying one option and selling another, generally the more expensive being hedged, protected, or partially financed by the cheaper option.

When options are expiring at the end of the trading day, all the characteristics of options are sped up. From a data driven standpoint, there are three key Greeks to consider. The two most obvious are Theta and Gamma which essentially battle it out for the day. But Vega also plays a key role, as big moves spike up Implied Volatility and option’s premium, and calmness can sap premium almost as fast. With hours or even minutes until the options expire, the Greeks’ calculations stop meaning as much as the concepts behind them.

Options sellers are banking on Theta eating away the premium as the day progresses. If the option ends out of the money at the end of the day, it is worthless. On the other hand, Delta will end the day at either 100 or zero and is likely to swing huge amounts during the day, which is the measure of Gamma, the change of Delta. So option buyers are looking for options to get in the money and run way up in value.

Since we are talking about expiration, it is important to understand the implications, which vary depending on what underlying the option is based on. Remember, there are four types of underlying securities, and at expiration the differences really stand out when an option expires in the money. For stock and ETF options, in the money options are settled with shares, which may not be the best outcome for day trading. In addition, while expiration option trading ends at the closing bell, expired stock and ETF options can be exercised until midnight, so even options that end trading out of the money still might be exercised if market conditions change after hours from news or earnings impact. Index options are much more straightforward. Index options are cash settled based on the price of the index at the closing bell. Because of this, index options, like SPX, are generally the preferred trading vehicle for traders holding options through the closing bell. Futures options settle with futures contracts unless the futures contract is also expiring the same day. However, futures options are assigned based on the price at the closing bell, not any after hours moves, so a trader knows at the bell whether there will be an assignment or not. So switching between underlying types for 0 DTE trades in not a trivial decision.

As mentioned before, because 0 DTE trades can rapidly change in value, having a mechanical trading plan becomes critical for consistent success. Most traders that trade short/selling strategies use stop losses to keep losses from getting out of hand, and long/buying strategies use some type of trailing stops or rolls to protect winning positions and keep upside unlimited. There are a few trades where holding to expiration (no matter what happens) could be considered, but I think 0 DTE are best managed by active trading based on market action.

So let’s get to it. Let’s discuss some typical strategies, both from the long and short side, considering what it takes to be successful.

Selling options with 0 DTE

Most 0 DTE option sellers I know actually sell spreads to define risk. Selling naked options on expiration day simply requires too much capital and carries too much risk for the average trader. The width of the spread can vary based on the strategy or capital available to the trader, but wider spreads tend to decay faster than narrower spreads. These trades are expected to win a high probability of the time, but to avoid severe losses, stop losses are also critical parts of the strategy.

While there are many variations of these strategies- different times to enter and exit, trading one side or both sides (puts and/or calls), entering or exiting all at once or legging in based on the market, the core of the strategy is the same. Sellers want to sell at a relatively high premium and buy it back for less or even let it expire worthless. I’m going to focus in on two common strategies that I have had success with and 0 DTE trading friends have done successfully- a wide Iron Condor and an Iron Fly. For discussion, let’s assume that we are selling spreads directly on the S&P 500 Index, ticker symbol SPX.

0 DTE Iron Condor

Iron Condors on expiration day seem to perform best way out of the money, selling options with 10 Delta or less and buying 30 to 100 points further out of the money. Greek calculations for 0 DTE can be flaky and vary widely, so many traders are more comfortable choosing strikes based on the premium available. For example, a trader may sell the lowest put strike that sells for over $1.00 or maybe over $1.50, and buy the put that sells for under $0.75 or $0.50. For perspective, you can estimate the expected move at any time in the day by adding the premium of the at the money put and at the money call. Generally, these strikes are between 1.5 and 2 times the expected move for the put being sold and another half expected move further for the put being bought as a hedge. So, it’s highly likely that the strikes will expire worthless.

Similarly, we do the same thing on the call side, selling a call and buying a higher strike call for less. If we choose similar Delta values, the premium for each call will be less, but the difference in premium may actually be more if we have the same width wings. It is a matter of preference as to whether to try to collect as much on the call side as the put side.

The risk vs reward for this set-up is the net premium difference between what was sold and what was bought and the difference between strikes. For example, if we sell a put for $1.50 and buy a put at a strike price 40 points lower for $0.70, we are risking 40 to make 0.80. Then, if our calls were sold for $1.20 and bought for $0.40, we have another 0.80 on another 35 wide spread. So in total we have 1.60, but still only 40 risk because the options can’t expire in the money on both sides. Actually, because the options are for a multiplier of 100, we risk $4000 to make $160. So, if all goes well, we make a 4% return on the capital needed in one day. Some traders sell slightly closer strikes to try to collect more premium, and others sell for less to improve probabilities.

While probabilities are fairly high that the strikes will end up out of the money, we never know for sure, so we have to protect our capital. Most traders I know use a 2x stop loss on each side. They limit their loss to twice the premium they collected on each side. So, if a put was sold for $1.50, losses are limited to $3.00 by entering a stop loss on the short put at $4.50. While a stop can be entered for the price of the spread, it isn’t recommended because during the day prices can vary in weird ways and stops can trigger on spreads when the price hasn’t really moved much. I’ve read numerous posts of traders who were frustrated by a stop that was executed when there position was in no danger because of a rogue quote. If possible, it’s best to have the stop trigger based on the bid price of the option if your broker allows it- for the same reason- to avoid bad quotes triggering a stop.

It can be frustrating when a stop triggers just as the underlying price hits the high or low of the day and reverses. A trader looks at this and thinks, “Gee, if I wouldn’t have triggered the stop, my option would have expired worthless. I took a 2x loss when I could have had a gain.” Unfortunately, a trader never knows when the price will reverse and when it will keep going. The goal is to stop our loss at 2x and not let it get to 10x or 20x. We can recover from small losses, losing all the capital of a spread trade can be devastating.

The Iron Condor is a 4 legged trade, so if one leg is stopped out, we still have three legs. On the side where the stop occurred, the long position will have gained value, although not as much as the short strike lost. We can hold the long strike in the event that price keeps moving, making the long strike more valuable. However, since the strike is likely still well out of the money, it is likely to expire worthless and probably is best to be closed out soon after the short strike stop occurs.

When we are stopped out on one side, it is even more likely that the opposite side will expire worthless. However, there is a small possibility that price action could reverse and move far enough to stop out the other side as well. For that reason, some traders will close out one side if the net premium has decayed 80 or 90% of the way while there is still a lot of time left in the day. The choice is take risk off the table, or hold out for that highly probable last 0.25%. Again, it’s personal preference.

So, let’s look at the various potential outcomes of our $1.60 Iron Condor:
1. most likely (~70%) both sides expire worthless $1.60 profit
2. sometimes (~25%) one side is stopped out and the other expires worthless ($3.00 loss on short stop, $0.20 gain on long, $0.80 profit on other side) $2.00 loss
3. rarely (~5%) both sides stopped out, assume no net gains from long strikes so $6.00 loss ($3.00 each side)
Adding all the probabilities together, we get an average return of 0.33 profit, or $33 on our $4000 capital. That’s just under 1% per day.

Can some traders do better? Yes, there are lots of variations that some traders believe give them a better advantage. But lots of traders do worse. Why? Because managing trades while sticking to a plan isn’t easy for most traders.

How can the trade be varied? Some traders enter the trade at different times in the day. They may enter at market open and again a few hours into the day. They may open on just one side based on technical indicators predicting movement in a certain direction. They may add based on one side based on market movement. They may have plans to add new positions when an old one is stopped out. Which variations work and which ones don’t? The probabilities are essentially the same but can be tweaked by collecting a little more or less in each trade.

Some may wonder why we wouldn’t just look at stopping out the whole Iron Condor when it loses twice the premium collected instead of managing each side separately. While it could be done that way, the challenge is that each of the legs of the trade are very dynamic in their values and the relationship between them changes dramatically during the course of the day. If the trade is opened early in the day, it is likely that by the final hour of the day only one position will have any meaningful value. Also, managing puts and calls separately allows traders to add and take away positions on either side independent of how they treat the other side.

On an ideal day for this trade where the market doesn’t move much after the Iron Condor position is opened, all the legs will decay proportionately and have little value left by the afternoon period a few hours before expiration. This is because expectations of the remaining move for the day will decrease and the price distance that was 1.5 times the expected move will become 3 to 4 times the remaining expected move. Since the probabilities are exponentially smaller of being tested, the premiums simply evaporate. One doesn’t have to wait to the very end to see the result.

Other days Iron Condor traders may see the price creep around moving toward one of their short strikes. Big moves early in the day can quickly lead to executing a stop, but the nerve-wracking position is the one is close to stopping out all day as the price moves ever closer to a strike price but not close enough to trigger a stop. For some traders this is stressful, for others fascinating. To avoid stress, many traders set their stops and go on about their day knowing that the market will decide whether the trade wins or loses.

Iron Fly 0 DTE trades

A completely different approach to capturing decay on expiration day is selling an Iron Butterfly or Iron Fly as it is more commonly called. The Iron Fly is created by selling an at the money call and an at the money put and buying protective wings outside the expected move of the day. The trade simulates a straddle, but defines the risk as the width of the wings to keep buying power reasonable. Most traders try to open these trades soon after the market opens and get out fairly soon, taking advantage of early morning premium decay as the market settles in.

As discussed earlier, the at the money put and call premium imply an expected move for the remainder of the life of the option. How big the expectation is varies from day to day. For example, on days when the Federal Reserve announces interest rate policy, the expected move is much higher than other days. Other anticipated news events can also trigger uncertainty about pricing changes to expect later in the day, driving premium higher. Other days, little news is expected and low premiums reflect that. So setting up this trade requires a review of prices to pick wing strikes that are appropriate.

Generally, most traders look for Iron Fly wings that are 1.5 to 2 times the implied or expected move. For example, if the total premium of the at the money put and call is $30, one might choose to buy puts and calls $50 away from the money. These should be fairly cheap compared to the at the money strikes. The idea is that there isn’t much decay left, these long options are simply protection from a sudden outsized move. An alternative is to use a set price for one or both of the longs, like $1 for the long call and buying the equidistant long put, which may cost slightly more due to pricing skew.

The most common management strategy I’ve seen for this trade is to set a win target and an offsetting stop loss, and let the odds play out. Iron Fly sellers pick either a percentage target or a dollar target for profit and typically set the stop loss at twice the win target. For example, one trader may target a profit of 5% of the premium, while another may target $1.50 profit every day. There’s logic for either approach, big values may hold value until the news event that is expected to move price, while low values may decay slowly. The key is that the bigger the target, the longer a trader is in the trade.

Why not go for it all and let the position expire? First of all, one short strike will definitely be in the money at expiration while the other short strike will be worthless. The day to day variation in results would be huge, perhaps making 50% return one day and losing 140% the next day. In addition, most studies I’ve seen on this approach suggest that this is a net losing trade over time.

The idea of getting in and getting out is that there are periods of time during the day, primarily at the open, when the level of uncertainty drops significantly in a matter of minutes or a few hours. Even with price movement, expected moves drop faster and the premium of the Iron Fly decays for a win.

In practice, the Iron Fly can tolerate a move of a few strikes up or down initially without stopping out. Early in the day the market often moves around searching for a price to stabilize on. The Iron Fly seller expects that movement to be small enough most days that a stop isn’t triggered and the settling price is close enough to the price where the trade started that the profit target can be achieved.

Setting a stop order or profit limit order is trickier with an Iron Fly than with the Iron Condor. The issue is that with the Iron Fly, a price move of the underlying generally impacts three of the four legs. One short goes into the money and the long on that side starts increasing in value, while the other short starts decreasing in value. The long on the untested side goes from low value to nearly worthless and isn’t a factor. A set and forget stop strategy would be to set a stop for the whole four legs, but triggers and fills can be inconsistent. Another approach is to watch the direction of price and set a stop for the three legs that are most impacted. Another is to set a mental stop and manually close if the price goes beyond your mental stop.

For example, let’s say we open an Iron Fly for $30 credit and target $1.50 profit. We can enter a limit buy to close order to buy the whole position back for $28.50. We could alternatively place a stop loss order at $33. Some brokers allow a bracket order that combines the two orders into one for a situation like this. If we want to watch and mentally manage the order, we may choose to only close the three legs that have meaningful value.

Time in the trade can vary from minutes to hours. Some days the price sticks right where the Iron Fly was sold and the price decays in 5-10 minutes. Other days, the price may grind away varying premium between the profit and stop targets for hours. Many traders set a time limit- if the trade doesn’t hit a stop or profit target in 2 hours, close it and move on.

Time to enter is a bit of a personal preference as well. Some traders try to enter within seconds of the market open when there is the absolute most premium available. Others wait five to fifteen minutes for the initial big move to stop. Some do just one of these trades a day, while others open several at different points in the day. Some avoid Federal Reserve days while others embrace them. There are advantages and disadvantages to each way of entering, but often it comes down to comfort of the trader with a chosen approach, the probabilities are similar.

Over time, the math is fairly simple with this trade. We need to win more than twice as often as we lose. The studies I’ve seen show this as a net winner. The other key is stay mechanical and respect identified stop values. Most people who fail at this trade do so by getting sloppy with their stops and hoping for prices to reverse while the loss multiplies. Discipline can’t be overstated.

Long Strategies for 0 DTE

Buying an option on expiration day requires a strategy that can overcome the rapid time decay of the option purchased. Since there are huge volumes being bought each day, there must be some validity to this approach.

Buy 0 DTE Straddle

One simple approach is to buy a straddle and hope for an outsized move. This is essentially the strategy discussed in the post on the 1 DTE Straddle I’ve written about separately, just done on expiration day. The difference is that at 1 DTE, there is overnight movement that may impact pricing, while once the 0 DTE trading day has started, we only have the day’s price movement to consider.

This strategy is essentially the opposite of the Iron Fly strategy and counts on movement of price to exceed time decay. Since risk is limited to the premium paid, there isn’t much value in selling wings, which would limit the upside of any move.

When would one open a 0 DTE straddle? Perhaps right at the open, looking to capture a big early morning move. Or just before a big announcement, like the Federal Reserve interest rate announcement or press conference. Or maybe at a point in the day where there is time left but the straddle is just very cheap and a small move will make it profitable.

The biggest challenge is deciding when to get out both for winning and losing positions. The position won’t expire worthless, so should there be a stop loss? When a position wins, when is the profit enough to justify the strategy over time? Since the trade has theoretical unlimited profit, shouldn’t we preserve that potential? Tough choices, so thinking through a plan ahead of time for the situation is critical.

My go-to plan is usually to roll in the money puts toward the current strike price when I can collect a significant percentage of the roll distance. Early in the day, I might roll my strikes $10 when I can collect $7. Later in the day I may do it if I can collect $8. The idea is to take some of my winnings off the table while allowing for additional movement to make more. I protect myself from a reversal wiping out my profit. I find this approach reduces the volatility of my win and loss amounts.

Jump on the Trend with a Long Option

Many traders like to use Technical Analysis to predict future movements of the market. They detect when a trend in one direction is starting and determine how long they expect it to last. A great way to take advantage is to buy a call when the market is trending up and sell it at the top before it has time to decay, or buy a put on a downtrend and sell it at the bottom.

Generally, the idea is to get in opportunistically and get out. Time is ticking against the option buyer on expiration day, so the buyer has to be right on direction and right on timing. If the trend is small or slow moving, premium will decay faster than the underlying price can increase it.

A typical strategy on an uptrend is to buy a call a few strikes out of the money. For SPX, this might cost $10 premium or $1000 for the contract. The Delta value might be 30, so that a $10 price move would net $300.

If the strike ends up in the money and is above 50 Delta, a roll to a higher strike should net at least half the distance of the roll. For example, one might roll up $10 for a $5 credit. Or wait to get further in the money where a roll up could net a higher percentage. Or just close the trade when technical analysis says that the move is approaching the top of the range.

The same basic strategy would work with puts on a downtrend. In either case, the market needs to move decidedly in the buyers favor for there to be a profit.

Time of day impacts premium pricing as well. Early in the day there is obviously more premium than late in the day. Buys earlier in the day can follow long all-day trends and make up for the high premium to get in. Late day buys can pay off quickly with a fairly small move in the direction of the trade. A trader has to be aware of the time left and manage accordingly.

The Binary Event

Often, the option premium and price movement of a day is greatly influenced by a single scheduled event. A piece of news, like an economic report, or a Federal Reserve rate announcement is often anticipated by the market with high option premium before the event and much lower premium after. These events are referred to as “binary,” in other words true or false, 1 or 0, good or bad. The impact of these events really have three outcomes for option traders- the market goes up, the market goes down, or the market basically doesn’t move. A trader doesn’t really know what the market will do, so how can we play one of these events.

A starting point might be to look at how much premium is elevated. Sometimes the market is expecting a big impact and sometimes a small one, and it often pays to be contrarian in regards to expected impact. How do we know if the premium is high or low? It takes only a few weeks of watching premium prices to grasp whether premium is higher or lower than normal, and if the high premium for a binary event is extra high, or actually a bargain. If premium is lower than normal, it might be a good time to buy options, either a straddle, or an out of the money call or put in the direction that the market is most susceptible to a big move. If premium is extra high, selling an Iron Fly or Iron Condor might make more sense.

Binary events tend to behave in crazy ways. When the initial news comes out the market may rocket in one direction for a few minutes and then reverse back to where it started or even switch from a big move in one direction to another. Most market observers explain this by noting that the very first reaction is from robot traders that look for certain numbers or words in a statement and interpret them as bullish or bearish, triggering large buys or sells. Then a combination of cooler heads prevail, as the market digests the information and puts things in context. After a while, the market decides whether to take the event as a positive, negative or neutral for the near-term future.

I know many traders avoid binary events because of the unpredictability of market behavior. There simply isn’t a built in probability advantage to any specific trade, and big losses are a distinct possibility. For traders that do like these trades, a plan for managing the trade is critical, when to get in, and a plan to hold, fold, or roll depending on the behavior of the market.

Conclusion

0 DTE trades are extremely popular now that they are available every trading day. However, that doesn’t mean that they are an easy way to make money. In many ways, they are the closest option trade to gambling that there is available. Gaining an edge requires developing and following a plan that accounts for both the potential movement of the market and decay of options. For traders that regularly trade 0 DTE options, it is critical to track all trades to make sure that the strategies used actually average a positive return over time.

I’m actually not a big fan of 0 DTE. For me it is too much drama with too little edge. The rest of this site is dedicated to other strategies that I prefer. But for traders that have the wits and discipline to trade 0 DTE, all I can say is “best wishes!”

2022 Learnings

In 2022 I had a rough year in many ways, but also had many successes, and need to take away some lessons from it.

Moving into a new year, it is always good to review trading in the past year to see what can be learned. 2022 is no exception. I had a rough year in many ways, but also had many successes, and need to take away some lessons from it.

Overview

2022 was a bear market year. Coming into the year, I was trading some very aggressive, short-duration bullish options positions, despite lots of warnings of troubles on the horizon. This resulted in a big loss in January and February, until I adjusted to a more neutral approach. However, I got away from many core philosophies and still didn’t recover as well as I could have.

What didn’t work and why

My biggest losses came from three main strategic mistakes, one that was new to me, and two that I should have know better. The new one was selling short duration without an appropriate exit strategy. The old should have known better losers were trading options on individual stocks and selling calls too close to the money.

Short duration trades

In 2021 I rode the bull market with a trade that was perfect for an almost straight up market, the 7 DTE rolling put spread. I’ve written about it, and you can read about how great it worked. However, when the S&P 500 went down over 400 points in a month at the beginning of 2022, there was no defense with the strategy of rolling. Because I had so much success with selling 7 DTE put spreads, I was reluctant to admit that the strategy wouldn’t work. I wasn’t prepared for a move down that didn’t bounce back. We had plenty of warning that the Federal Reserve was going to stop pumping money into the economy and instead raise interest rates and reduce the money supply. But, I left myself exposed with lots of short duration put spreads as the year began.

I tried to fight the down moves with rolls and a variety of other tricks I’ve used over the years, but there really was no defense for short puts close to expiration in a plummeting market. As I’ve come to learn, in down markets puts can be underpriced for the risk, and short duration puts can actually be a good buy. The book “The Second Leg Down: Strategies for Profiting after a Market Sell-Off” by Hari Krishman details a number of studies to back this up.

I’ve heard from a number of people that they had success with short duration options even in 2022 by going a little further away from the current price and either holding or using stop losses to keep losses from getting too big. But, I didn’t do that. Later in the year I tried to get back into selling some short duration options and got burned again. My style of rolling is just not a good fit for short duration options.

So, as expiration approaches, there is a lot of time decay that is very tempting to take advantage of. The flip side is that to get that decay, options must be sold quite close to the current price making them susceptible to a sharp move. Short term move of several times the expected move are not uncommon, especially in a bear market. For me, the returns are not worth the risk. My temperament is just not set up for this kind of trade.

More time gives more forgiveness. Looking to reduce risk from short duration options, I’ve focused studying ways to get the most out of longer duration options. I’ve done additional research on optimal Delta for selling put spreads at different time durations to maximize Theta. I’ve also gotten back to waiting for down days to sell bullish put strategies.

The only short duration trade I’m currently doing is an opposite trade to most of my other strategies. I’m buying 1 DTE straddles, as I’ve written about in a previous post. So far, so good with that.

Selling Calls too Close to the Money

Even in a bear market, selling calls can be painful. In a bear market there are often large counter-trend rallies where calls with strike prices close to the money quickly end up in the money. Implied volatility on index options is almost always significant skewed to the downside, making calls cheaper than puts. Selling the lesser call premium tends to not be adequate for the risk of a big rally. When I combine selling calls close to the money and with fairly short duration, I set myself up to be whip-sawed back and forth, reacting to each move in ways that locks in losses each way.

Ideally, I want to have positions outside of the market moves, far enough away in time and price distance that day to day price changes have little impact on me and I can just wait for time decay to work my option prices down over time. Puts tend to have more strategies that can be profitable when selling than calls. If you don’t believe this, just try back testing short option strategies and see if you can find one where calls beat puts- I haven’t found one.

Selling Options on Individual Stocks

I’ve written a number of times about how indexes are much less likely to have extreme outsized moves than individual stocks. 2022 is a great reminder of that. Many formerly valuable stocks lost well over half their value during the year, and a number of them lost over 90% of their value. I was exposed to some of this mayhem when I sold puts well out of the money on a few that seemed like they couldn’t miss, but then did.

I completely botched a trade on a company that I really like. Generac makes back-up generators as well as systems that store and manage electricity generated from solar panels. With the electrical grid getting less reliable, people are in need of their products. So, to mix it up a bit, I sold at $20 wide put spread in the low 200s early in the year after the stock had fallen significantly and seemed to be on an upward trajectory. Despite all their success in the market, the stock slowly declined, and I found myself rolling my position down and out a few times. Then, I made the fateful decision to sell my long put of the spread and switch from a put spread with $20 risk, to a naked put with a strike price of $200, cash secured. I figured that the stock was surely at the bottom of its range, and I wouldn’t mind owning it if it dropped a little more. Then Generac announced that they were going to miss earnings substantially because of a lack of installers available to deliver and install their equipment at residences. Overnight the stock dropped 30% after previously losing over 20%. Before I knew it, I was stuck obligated to buy a $100 stock for $200. I tried to roll out, but there were no takers to make a trade. I was assigned the shares, losing $10,000 per contract on a trade that originally had a max loss of $2,000 per contract. Multiple bad ideas- individual stock risk, getting cute when tested, not accepting a loss and moving on.

I also sold puts on ARKK, the Ark Innovation ETF. It’s not an individual stock, but it is a volatile managed fund of a relatively small number of innovative companies. Again, I thought that we had seen the worst of the market drop, especially for this fund, and I sold cash secured puts in the middle of the year. Since then, the stock has fallen by half- I had about a 10% cushion to start, but that is long gone and now I have shares.

There are some others that weren’t that bad, but the conclusion is the same. Options on major indexes are much less likely to be hit by outsized moves, particularly if there is a decent amount of time until expiration and the strikes are well out of the money. That is one of my core mantras and I strayed at my own peril.

What went well

Fortunately, not everything went as badly as the trades described above. I re-discovered some strategies that I had stopped using that worked well, and started using some new strategies that I was either skeptical of or unaware of prior to putting them into practice.

Selling Long Duration Puts

I’ve sold puts well out of the money well out in time many times in the past, but the allure of big Theta from short duration started getting the best of me. Why sell at 6 weeks or 12 weeks when we can make bigger returns selling at one week? Well, lots of reasons. Short duration takes lots of effort and is much more stressful. It doesn’t take a big move to blow past strikes that have value less than a week until expiration, while positions outside of the expected move a month or more out in time are much less impacted.

With positions 4 to 6 weeks out or even more, we get more consistent results and can reduce volatility of the portfolio. When a big move happens, we can wait a few days to see if the move reverses before making any adjustments. Often it does and there is no reason to intervene.

I’ve found that I can still sell spreads with Delta values in the teens that are in their maximum percentage of decay weeks or even months before expiration. While the percentage return isn’t as high as short duration, it is more consistent and higher probability of being positive. It isn’t exciting, but that’s okay.

Put Ratio Trades

The most popular page on my site every month is my explanation of how I trade broken wing butterflies. For a while I got away from trading this, chasing some other “shiny object.” I re-started trading the strategy and got back to winning. I have been a little more opportunistic with this strategy, opening on down days to get my strikes lower with higher IV, but the trade is high probability with rapid decay. The way I trade it seems to be just far enough out in time to buffer it from the volatile weeks that have come along regularly in 2022.

I’ve also had good success with the other put ratio cousins of this trade, the broken wing condor (or 1-1-1-1), and the 1-1-2-2 trade. The common thread to each of these is that there are two competing spreads in each case. I start with a debit put spread, typically where I buy a 25 Delta put and sell a 20 Delta call which acts as protection for a higher priced and wider credit put spread at lower delta values. The wider and lower Delta valued credit spreads decay faster than the narrow debit spread, and often switch from a negative value overall position when sold to a positive value position that I can sell to close prior to expiration. This happens when the wide credit spread decays to the point that it has less value than the narrower debit spread. So, I often collect cash when I open and collect cash when I close these.

Finally, I’m seeing success in the naked versions of these trades as well. Instead of having two spreads, I sometimes skip using the low long leg of the credit spread and go with selling a naked put. This leaves me with a debit spread protecting a naked put or two below it. So I end up with 1-1-1 or 1-1-2 versions of the above trades- true ratio spreads. These have undefined risk to the downside unless cash secured, and I trade them on margin. That ties in nicely with some of my other take-aways.

Using Futures Options to Pump Up Returns

After avoiding futures for many years, I’ve really become fond of them. I avoided them because I didn’t see the strategic value of buying or selling futures contracts on an index or commodity. I was also scared by the risk of aggressive use of SPAN margin. But what I’ve found is that futures options in particular allow me to sell high probability positions for very low amounts of capital, and then allow me to buy or sell actual futures contracts to use as a hedge and neutralize overall Delta. It can get complex very quickly and a trader has to be avoid building a house of cards that could collapse in a outsized market event. But when used with care, futures options and futures themselves provide valuable tools to increase returns.

I haven’t written much about the use of futures strategies on this site because I’m still working to distil the approaches into content that can be readily applied. Risk vs reward becomes much more significant with futures options, so risk management becomes a primary consideration in every trade and isn’t something to jump into without a comprehensive understanding.

All that said, I’m finding futures options allow me ways to magnify returns and also hedge my risks. I’ll be writing more in subsequent strategy discussions, but if you look at pages on four different underlying types and four levels of risk, there’s some initial content to consider. One specific hedge trade I’ve started using, the 1 DTE Straddle, came from my futures experience.

Selling Naked Futures Options

One place where I’ve found success with futures options is selling naked options well out of the money well out in time. Because of SPAN margin, these trades don’t require much capital. They also don’t move that much because of the long duration. I’m finding trades with lots of decay and really seeing the appeal of naked options. Long duration and low deltas cushion the positions from big day to day moves and give me plenty of warning to adjust when needed. While spreads have windows where they can be rolled for credit and other Delta values where they can’t, naked options can always be rolled out in time for credit. The issue is that some rolls are more lucrative than others.

So I finally see the flexibility and adjustability that naked options provide in defending against big price movements. The key is to manage size to keep risk reasonable.

Naked to me involves a variety of strategies from selling a single option, to selling the naked put ratio trades mentioned above. As I better define consistent management and hedging approaches to these trades, I’ll explain my naked strategies in more detail.

Using Research to Test Strategies

Finally, I’ve re-discovered the importance of doing my own research to understand trades I’m doing. I’ve shared many of my insights on this website, but I always have new ways to look at trade set-ups, impact of management, and understanding risk. I’ve written about the sources I use to research the market, and I still use the same primary approaches. I use current option tables, I do backtests, I analyze historic trends, and I model potential outcomes.

Sometimes it is easy to get caught up in what I’m doing every day and not stop and ask if the approaches I’m using at the moment are really valid. I don’t look to see if there is a better way. Research keeps me fresh, and often validates findings I’ve observed in the past, but strayed away from in my current trading. So, constantly looking at data from different strategies in different ways actually keeps my trading focused on approaches that work.

I also find that the biggest beneficiary of the studies I share is me. Writing things down to share makes me double check my work and get clearer as to what I’m doing. Sometimes in the course of providing data for a trading approach I’m doing; I realize that I could do better, and revise based on what the data says.

I also get a lot of inspiration from other sources- groups I’m a part of and sites I follow. My favorite source of inspiration continues to be TastyLive, which I often have playing in the background while I trade. I interact with a lot of other traders which also helps. I’ve written about the value of community in the past.

So my final thought is that I need to challenge myself to always keep learning and base my trading strategies focused on proven approaches with high probability of success and manageable risk.

Best Delta for Rolling Put Spreads

I’ve noticed some put spread rolls collect more credit than others. This study shows that there is an ideal Delta for rolling put spreads

After trading put spreads for several years, I’ve noticed that some rolls collect a lot of premium credit, and others are a struggle to collect any credit at all. I decided to study this to see if I could find if there is a “sweet spot” for rolling put spreads based on Delta values. I’m happy to report that there is.

It’s no secret that if a put spread gets fully in the money, it is impossible to roll to the same strikes in a later expiration for a credit. But when a spread is out of the money, I’ve seen a wide variation in credit when I roll, and I’ve often thought that there must be a best place to make a roll to get the most credit. If there is, I could devise a strategy to take advantage. So, I copied some option tables into Excel and pivoted the data a few different ways to figure out how premium from rolls vary.

Before jumping into the study, let’s discuss what rolling option spreads involves and why we might do it when a spread is out of the money. Rolling is one three ways to manage an exisitng trade- I covered the three ways in the page on managing by holding, folding, or rolling. One of my common management techniques is to continuously roll a position- I let the short spread decay in value, then roll it out in time to get more premium, and then let it decay all over again. Just repeat over and over. For those not familiar with the roll concept, rolling means executing a trade where an existing position is closed and a new position is opened all at once in one trade. The new options may be at the same strikes, which would be rolling “out,” or the strikes may be higher, which would be rolling “up and out,” or we could also roll “down and out.” Rolling a credit put spread that is out of the money out to the same strikes, will almost certainly generate a credit, which is the goal of this strategy. I’ve discussed this -approach in detail in other pages of this website, including roll for 6 percent a week, goals for rolling Iron Condors, the power of rolling Iron Condors, and rolling losing positions.

Rolling Spreads in the Study

I looked at a lot of different combinations of rolls, different durations, different times between durations, and I saw similar results. In the interest of keeping this write-up from getting lengthy, I’m choosing to just show a few examples.

7-10 DTE Roll

While I don’t trade a lot of options with durations of a week or less, I thought it would be good to look at this timeframe as the lower end of timeframes where we get outside of current week expirations. The following chart shows all the available combinations of 40 wide 7 days to expiration (DTE) SPX credit spreads rolling to the same strikes at 10 DTE.

Rolling out from 7 DTE to 10 DTE has the best credit when the 7 DTE short strike is between 10 and 20 Delta. Note that the Theta peaks at a slightly higher Delta.

I’ve shown the net credit for each roll combination, as well as the raw Theta difference for each existing 7 DTE 40 point wide spread. The x-axis is the Delta of each 7 DTE spread. The roll credit is shown on the left axis, and the net Theta is shown on the right axis. Looking at a peak value of approximately $1.20 per roll, we would collect 3% of the 40 wide spread. Meanwhile, the peak Theta of around $0.45 per day would equate to 1.1% of the width. So, holding might get a similar daily return, but with increasing risk as expiration approaches, but a roll would allow us to collect 3% and still collect additional Theta over again. Actually, that’s double counting. The Theta would just be the decay of the premium we are collecting. Just a few ways to think about the transaction. We can also look at actual strike prices and look at a few other values.

This graph shows roll credit plus Delta and Theta values for the positions

On this next chart, I’ve shown the x-axis as the strike price of the short put of the credit put spread. I’ve also added the Delta values of each of the puts for the 7 DTE spread as well as the Delta of spread position. In addition to the net Theta of the 7 DTE spread, I added the net Theta of the 10 DTE spread that we would roll to. So, each strike price on the x-axis is tied to six different pieces of data for a potential spread roll. While the roll premium and net Theta of the 7 DTE spread is the same information as the previous graph, the additional data can add more context.

Note that the Theta values of the longer duration spreads are generally lower than shorter. That should be expected. More time means slower decay. But the new spread will have a slightly higher Delta, which moves the peak of the Theta curve down in strike prices, because as we have seen in our study on maximizing Theta for a put spread, Theta tends to max out at short Deltas around 20, which will be further down after a roll. So, note from the chart that the maximum roll premium lines up for the most part with the maximum Theta of the spread we are rolling to.

The take-away from the Delta information on the chart is that as we get closer to the current price and have higher Deltas, the net Delta goes up, and the value of rolls goes down. Also, if Delta gets too low, there isn’t as much premium available in a roll to the same strike prices. I picked out the Delta values of the spread with the highest roll value, and it is approximately 14 Delta on the short strike and 8 Delta on the long strike.

So, the ideal scenario is to start with Deltas of around 20/13 and see the positions decay and Deltas to decline to 14/8, and then roll out to new strikes with Deltas of 20/13. If only the market would cooperate with our plan and let us do this all the time. Obviously, the market isn’t that consistent, so we have to manage in other ways.

Sometimes, we may want to roll down and out. Let’s look at the premium for 40 wide spreads and see what is possible if we want to collect a credit.

Looking at the premium differences, we can see opportunity to roll down at some strikes more than others.

On the above chart, I have plotted the premium value of 40 wide put spreads at 7 and 10 DTE, along with the premium collected to roll out to the same strikes. I’ve also highlighted possible rolls down and out. The highest strike where it is possible to roll down a strike and collect a credit is to go from 3920/3880 at 7 DTE to 3915/3875 for a 10 cent credit. When a spread is being tested, every bit helps, but clearly this roll doesn’t give the position much more breathing room. On the other hand, if we had the 3800/3760 spread, we could roll down 25 points to 3775/3735 for no cost. So, again it pays to stay away from being tested. But at this short of timeframe, it doesn’t take much of a move to get a spread in trouble, so let’s look at how a little longer duration would fare.

21-42 DTE

Let’s look at an example that generally matches up with the common strategy often associated with TastyLive.com. Interestingly, values peak out at about the same place based on Delta.

This example shows rolling from 21 DTE to 42 DTE, essentially doubling the time until expiration.

Again, the best premium for a roll is in the mid to low teen values of the Delta value of the short strike of the 21 DTE spread. Here we are collecting just over $6.00 to roll our 100-wide put spread out to 42 DTE. In that case, we would be collecting an additional 6% of the width of the spread. The 21 DTE spread would be decaying about $0.30 per day, so the roll allows us to collect around 21 days of decay in cash.

Notice that the observations we made on the 7-10 DTE roll hold almost exactly the same on the 21-42 DTE roll, even though we have much higher time to expiration, wider spreads, and proportionally longer rolls. One difference to note is that amount of premium and Theta are much less on a daily basis, but that should be expected as daily decay for similar Deltas gets higher as expiration approaches.

This graph shows the premium levels of 100 point wide spreads at 21 and 42 DTE, as well as the premium collected to roll out at the same strikes.

Another key difference is the distance that our strikes can be from the current price, giving the position more wiggle room for price changes. The above chart shows the premium of the various spreads available at 21 and 42 DTE. Notice that the lower strikes approach zero value while the spreads at higher strikes approach 100, which is the width of the spread and would be maximum loss for a credit spread at expiration. With spreads, the closer expiration gets the more of an S-shape we get when charting the premium. Since we are selling the spread, we’d like to see the value decay, either by staying out of the money as time goes by, or seeing the price go up, which would shift all the lines to the right on the chart.

What if we want to roll down to lower strikes when rolling out from 21 to 42 days? Let’s look at what would be available by zooming in a bit to the chart above to the area where there is credit available to roll out.

In this chart, we can see that the further we are out of the money, the more we can roll down for a credit. Once a spread is in the money, the opportunity to collect a credit is gone.

With plenty of time to expiration, we can roll out for nice credit or roll down quite a ways for some credit. For example, in the chart above, the 3700/3600 spread could be rolled down 150 points to 3550/3450 for 20 cents credit or rolled to the same strikes for $7.50 credit. The closer our strikes are to the money, the less credit we get to roll and the less we can roll down for a credit. And as we’ve seen, if our strikes are in the money, we would have to pay a debit to roll out. Having more time allows us to sell spreads that are much further away from the money and be able to roll out and away much easier than spreads that are closer to expiration.

42-49 DTE

One last example for contrast, we will roll out a relatively short amount of time from a 42 DTE put spread.

Again, we compare rolls at different Delta values, along with the net Theta of our current position.

So, this roll is from 6 weeks to 7 weeks until duration. However, our previous observations generally hold. The peak premium is at a bit higher Delta, in the high teens. This makes sense if we consider that we are only rolling out for about 16% more time, so our new spreads will have peak Theta much closer to our old spreads. This would point to the idea that the best roll is the roll that gets us to a new spread with a short strike Delta of around 20.

Again, our max roll amount equates roughly to the daily Theta multiplied by the number of days we are rolling out.

How to Use This Information

Readers may wonder, what good is this? A trader can’t really control where prices move to, so the Delta value is not really controllable by a trader. This is somewhat true, but prices do move up and down all the time, and so if I’m looking to roll out to get to a timeframe that has less volatility, I might be able to enter a limit order that seeks to collect close to the maximum roll credit possible. Often, I’m not in a big hurry to roll, so I can check out where the maximum should be and set up an order for 90% of that amount and go about my business. If it doesn’t execute after a day or maybe even a week depending on the timeframe of the position, I could change the order to something less lucrative.

Another way to look at this data is to realize that if my position has both strikes down in the single digits of Delta, I’ll likely want to roll up my strikes when I roll out to get to optimal Theta. On the other hand, if my position has strikes with Deltas in the twenties or thirties, I may want to try to roll down and out, and hopefully still collect a credit.

If my position has gotten even closer to the money or even into the money, I’m going to have trouble rolling for a credit, and I have some tough decisions to make. I need to consider all my choices: holding, folding, or rolling. If I’m deep in the money I might consider taking desperate measures. It all comes down to risk appetite and an overall plan of action. It’s best to have a plan for all possibilities ahead of time, and not try to figure it out when times get tough.

Final Take-aways on rolling put spreads

My thought process for looking into this was to find optimal credits for rolling spreads, so I could devise strategies to improve my results. After studying this, I was excited to find an answer that makes sense. Deltas in the teens for the short strike of the spread are ideal for rolling. The further out in time the roll is as a ratio of current DTE to future DTE, the lower the delta of the current spread for best credit from the roll.

A good starting point for estimating the best credit is to take current Theta of the spread and multiply by the number of days that are being rolled out. So, if Theta is 20 cents and the roll is going out 5 days beyond the existing spread, the best credit will be around $1.00.

Finally, realize that this study was for put spreads, not call spreads, iron condors, or naked options. Spreads have unique characteristics compared to naked positions, and their behavior does not translate over. So, I only apply this information to rolling put spreads.

I am studying how naked puts best roll as well and plan to do a write up in the future on the topic.

Goals for Rolling Iron Condors

The goals of rolling are to neutralize delta, harvest profits, collect credits, and widen body width of the Iron Condor.

I see four ideal goals for executing a roll of any position, but specifically Iron Condors. First, I want to neutralize the position delta. Next, I want to harvest profits from the existing position. I also want to collect a net credit with the roll from the old position to the new. And finally, I want to improve probabilities of success by widening the body of the Iron Condor. If I can achieve all four, that’s the quadruple crown of rolling.

Often I see posts in social media lambasting rolling positions as a way to lock in losses and having no point. While that can be a possible scenario, I’d like to take a moment to discuss the ideal outcome of a roll, and share a recent example of what we are striving for with a rolling strategy.

For more information on the initial setup of Iron Condors, refer to my earlier post on the subject. This post is meant to build on that earlier post.

Example Iron Condor Roll

Earlier today I rolled an Iron Condor from 36 days to expiration out to 43 days to expiration. I opened the old position 10 days ago when the market was a little higher. Today, I wanted to better center my position to bring in my position Delta, and be less at risk for a move up. So, I rolled both sides up, rolling the calls up 20 points and rolling the puts up 10 points, which widened the body of the Iron Condor from 120 points to 130 points. Here is a summary of the old and new positions, with key points highlighted for further discussion.

Let’s look at each goal and see how I did.

1. Neutralize Delta

While I don’t track Delta in my trade records, I do look at it for my open positions every day. For background on what Delta is for an option, a position, or a portfolio, see my posts on the topic. The account with this position was showing a lot of negative Delta, so I wanted to bring that in to a more neutral amount. Specifically, this position had a position Delta of -4.7, which equates to a Beta-weighted Delta of -47. This would be the equivalent of being short 47 shares of SPY. With my short call strikes slightly in the money, I wanted to reduce delta, get out of the money, and get more time. Rolling out a week accomplished all of that.

By rolling up 20 points, I got my short call out of the money. I rolled out a week, so I have more time. But most importantly, I cut my Delta almost in half from -4.7 to -2.5. I’m not zero delta or completely neutral, but it is a move in the right direction. I try not to over-adjust and chase being neutral too much or I can get whipsawed back and forth. So, now my premium value will be less volatile as the market moves up and down. Goal 1 accomplished.

2. Harvest profits from old position

The market has moved the direction I was positioned for, and today seemed like a good time to roll and recognize some profit. I’ve been in this position for 10 days, just over 20% of the life of the option. I’ve had some help from all the main pricing factors- price has moved down while I had negative Delta, time has passed while I had positive Theta, and volatility has come down slightly while I have negative Vega. All good for me. Notice that my put side lost money and my calls made money. I track them separately which helps me see trends, but the goal is for the net profit to be positive. And this position made $611 over 10 days. That’s around 8% return on capital. Goal 2 accomplished.

3. Collect a net credit from the roll

With a roll up on both sides, I had to pay a debit to roll up the calls, but I collected a bigger credit to roll up the puts. So, the net of the transaction is that I collected $0.35 per unit, or $35 overall. I try to collect credits in every roll because this is cash going into my account, while debits are cash leaving my account.

This old position wasn’t centered, and I widened the position while rolling out, factors that limited my net credit. However, I was able to find strikes that accomplished my other goals while still collecting a net credit. My new position isn’t ideal, but it is better than where I was and I got paid to make the change. Setting up a roll is an exercise in balancing many different desires, and I focus on collecting a credit as a way to determine how far I can go with my other desires. It isn’t a lot, but I collected a credit, so Goal 3 is accomplished.

4. Widen the body of the Iron Condor

The body of my Iron Condor is pretty narrow. How do I know? Look at the profit profile and it is clear that the whole position is inside of one expected move either way. Ideally, I’d like to get the expected moves inside my short strikes, but I’m managing a trade that is much tighter. So, every chance I get, I want to widen the body, the distance between the short strikes. Why do I want to do that? Because wider strikes have faster decay, up to a point, and we aren’t near that point. This position has strikes close to the money and the Theta values of the longs tend to cancel out the Theta of the short strikes more than I’d like. And the wider the distance between short strikes, the higher the probability of the price staying out of the money. Over several rolls, I want to get wider to where the position can tolerate moves without getting into the money as often. I went from 120 points between short strikes to 130 points, so Goal 4 is accomplished.

Quadruple Crown!

This roll accomplished all four of my goals for an Iron Condor roll. As I mentioned, I had to make some trade-offs along the way to accomplish all four goals, but this is an example of how I use all the data at my disposal to pick the trade that best suits the current situation.

Not every roll can be hit all four goals. If the current trade is a loser, the best you can do is meet the other three goals. Sometimes, I have to miss one goal to make another. In those cases, I choose based on what goal I’m most concerned with- do I need to neutralize delta more than I need a credit, or do I need to maintain body width more than I need a credit? Generally, I have a good shot to meet most of my goals if the current underlying price is inside the short strikes. As short strikes go deeper into the money, it becomes more and more likely that a roll will miss many of my goals.

This mindset of positive goals for trades isn’t exclusive to Iron Condors, but I thought today’s example would be a good way to illustrate the thought process involved in rolling for positive outcomes.

The power of rolling Iron Condors

In the bear market of early 2022, I re-discovered a strategy that I had mostly discarded during the bull market of the preceding years, the Iron Condor. The Iron Condor is primarily a neutral trade that when managed with aggressive rolls can provide good returns in choppy, down-trending markets. My goal is to maintain a position that can tolerate fairly big market moves up or down, while benefiting from time decay.

I had discarded the Iron Condor trade because I found I was always losing on the call side of the Iron Condor. Initially, I liked the idea of making money on both sides, but I found in a constant up market, I often lost more money from calls than I made from puts. So, I switched to mainly put spreads and other short put strategies, which did great. But then 2022 came along, and it was clear that the market was no longer going up, and that we were heading for a bear market. I started adding credit call spreads to my credit put spreads to balance risk and have a neutral strategy. Over time I saw that some of my set ups and management strategies were working better than others, so I investigated and came up with a process that now works well in the current bear market environment.

The basic setup of an Iron Condor

Selling Iron Condors is an extremely common option trading strategy. The strategy is a combination of two calls and two puts, four separate options working together. Usually, an out of the money put and out of the money call are sold, and then a further out of the money put and call are purchased to define the risk and reduce cost. The trade wins at expiration if the price ends up between the short strikes, and hits max loss if the price moves beyond one of the long strikes. However, I rarely if ever hold to expiration and roll my position way before expiration is a concern.

Here is an actual California Condor with a profit curve of an Iron Condor option trade drawn over it.

An Iron Condor is named after the shape of the profit curve at expiration, which kind of looks like a condor with a bit of imagination, kind of like how star constellations are named. The iron part of the name designates that it is made up of a combination of puts and calls, as opposed to a put condor, or call condor which has four legs of the same type of contract. An example of a put condor is the broken wing put condor strategy I have described in a separate post.

To build on the condor metaphor, the difference in option strikes are often referred to as the body and wings of the combination trade. The body is the difference between the short put strike and the short call strike. The wings are difference between the call strikes or between the put strikes. The wings on the puts may be equal in width to the wings on the call, or they may be different. Wings that are different widths might be call unbalanced, or broken wings, as the profit profile will no longer be equal levels each end of the price ranges of the trade.

My preferred Iron Condor setup

What I have determined works best for my management strategy is to use the S&P 500 index options (SPX), targeting a starting point 28-35 days from expiration, with option Delta values of 30 for the short strikes and around 20 for the long strikes. I like equal width for the put side and call side, so the Delta values for calls will be a bit wider than the put side, and the net Delta of the Iron Condor will be slightly negative. With implied volatility between 20 and 30%, I generally target 100 wide wings, with the body between the short put and short call of around 15o points on SPX.

Premium and Greeks for Iron Condor — Here is the setup of an actual trade from early 2022 on SPX using the criteria from this post. In this example 30% of the wing width was collected, and a little lower deltas were used.

Profit Curve — For the above example trade, the goal is to keep in the profit zone for the first several days of the trade- the positive area under the 21 DTE curve.

I use SPX because it is the least likely underlying to have outsized moves. It is also very liquid to trade, has tax advantages in taxable accounts, and has expirations multiple times per week in the timeframes I trade. Depending on account size or type, other option products for the S&P 500 may be appropriate and can be used instead with essentially the same strategy. Other indexes or even individual stocks can be used, but managing can tougher with bigger moves, less expirations, and less liquidity.

I use 28-35 days to expiration (DTE) because my position can tolerate most reasonable moves while still having decent decay. I’ve used timeframes as low as 7 DTE, but find that many one day moves can push a position out of the profit zone, and I find myself fighting a losing battle too often. Longer durations of up to up to or over 100 DTE can work, but decay is slower, and there are very few expiration choices to roll to for the way I like to manage. All that said, my plan can vary to different timeframes, with the goal that I will only hold the position for somewhere between 1/10 and 1/5 of the time left to expiration- for example, a 30 DTE would be held 3-6 days before rolling, while a 100 DTE position would be held 10-20 days.

I choose 30 delta for short strikes and 20 delta for long strikes because they are the most forgiving in a move, while still offering reasonable decay as a spread. Higher deltas allow for more premium to be collected, and price movement will often be well tolerated as the long strike of the tested side will increase and the short strike of the untested side will decrease in value, compensating for much of the increase in value of the tested short strike. The goal of my management strategy is to keep this relationship intact, so that price movement has little impact on my option position value. I think of the area where deltas of the four options balance each other out as the profit zone. Staying in the profit zone allows Theta, or time decay, to do its work and deliver profits. I have used strikes with a bit higher delta values, but if too high, the two sides will get tested more often and then require more management. In the past, I often used lower delta spreads for safety and better percentage decay. However, I have discovered that low delta positions don’t actually tolerate price movement well because the untested side of an Iron Condor quickly runs out of premium to offset any of the movement of tested side. This observation has been a game changer for my use of Iron Condors.

I use equal width wings on the Iron Condor for a couple of reasons. Equal width seems to tolerate price movement, both up and down. Equal width also leads to a net negative Delta position, decreasing the total position profit when prices go up and increasing profit when prices go down, which is good in a bear market where downturns are frequent. Negative delta actually is somewhat neutral if the value is only slightly negative- Iron condors also have negative Vega, or decrease profit when implied volatility goes up. So, typically when prices go down, implied volatility goes up, and impacts of the negative Delta and negative Vega cancel each other out.

My Iron Condors are opening somewhere around 50% of the width of the wings. For example, if I have 100 wide wings, I would expect to collect $50 premium. I initially resisted this, thinking that the probabilities would be too low. However, since the time in the trade is so short, and I plan to actively manage moves against my position, I find that the risk reward ratio becomes favorable. However, the example trade that I’ve used is a little wider body and collected only 30% of the width.

Strikes compared to EM — This chart shows previous market movement at the time of entering a trade, along with the expected move based on implied volatility and boxes to illustrate the strikes of the Iron Condor. The dates are the opening date, the expiration date, and the planned target date to close. This trade used long strikes that were at the expected move at expiration.

I have devised a graphic that may help to visualize this setup in regards to the expected move and time frame of the trade. The graph has several components- a historic rendering of what the index has done for the past several weeks, a curve showing the expected move for the next several weeks based on current implied volatility, and two boxes to represent the put and call strikes shown from the time of opening until expiration, and the target date to take action. My point with this chart is to show that while the strikes chosen are within the expected move at expiration, they are outside the expected move through the time I expect to be in the trade before I manage it. Said another way, if the position were held to expiration, it is very likely it would be breached on one side, but because the plan is to manage early, a breach is not likely- it would take an outsized move beyond the one standard deviation expected move.

Managing the trade with rolls

I manage my Iron Condor with what I think is a fairly unique rolling strategy. I roll my positions out in time and change all strikes in the direction that price has moved. If price goes up, I roll all the strikes up. If price goes down, I roll all the strikes down. I just roll whichever way the market goes. Here’s the interesting part- if I keep in the “profit zone,” I can roll up or down for a net credit with each roll, and my existing position will have a net profit. Usually, one side will be sitting with a profit and one side with a loss. The losing side is being tested- its strikes have higher deltas than when the trade started. The profitable side will have lower deltas than when the trade started. My profitable side should have a bigger profit than the loss of losing side. When I roll, I will likely have to pay a debit to get my losing tested side back to a good set of strikes at the new expiration. However, I should be able to collect a bigger credit on the profitable untested side than my tested side cost. Ideally, every roll is closing a profitable trade and collecting a net credit to open its replacement. All of this sounds great, too good to be true, but there are a number of details to unpack.

The first challenge is to stay in the profit zone. My general rule is that if I keep my untested short strike must never drop to a Delta value below 15. The reason is that when the Delta of the untested side gets below this point, it quickly stops being able to meaningfully contribute to offsetting price movement in the tested direction. For example, if the price drops, the short call will get further out of the money and drop in value, while the puts will go up in value. For a while the Deltas will mostly balance each other out, but as the Delta of the short call drops below 15, the put spread will start increasing much faster and the calls decreasing less. If this happens, it is time to act and roll all the puts and all the calls down to where there is again premium on both the put and call side. If price has gone up too much, it’s time to roll up all the puts and calls.

Actually, I try not to wait until the untested side gets to 15. I think of my position of having three possible states, green, yellow, or red. Green is when both short strike’s Deltas are above 20- everything is great and there is nothing to do. Yellow is caution, one of the short strikes are between 20 and 15, and probably will need to roll soon. Red is stop and take action, one of the short strikes is 15 or below, so it is time to roll immediately. So, my choice is clear for Green or Red, but I need to use some judgement in the Yellow state. If the day starts in the Yellow, I am more likely to let it ride for a while and watch to see if it recovers or gets worse. If the market has trended throughout the day and moved into the Yellow, I am likely to roll before the end of trading so I don’t end up deep in the Red overnight. If there is a strong trend pulling the position quickly toward Red, that may also be a good indication to act. Yellow is a judgement call.

I find that it is harder to have a profitable, credit roll when tested on a quick up movement. As mentioned earlier, equal width wings means that there will be a negative delta overall, and while volatility reduction can help, big up moves can be hard to stay on top of. That’s why this strategy works best in a bear environment, when the market is trending down.

Don’t over manage. Markets bounce around a lot, and it can be tempting to want to act on each little trend that happens. If I have the right strikes- the right body width and wing width for the market conditions, my position should be able to tolerate price movement. If I’m trading at 30 DTE, I want to wait 3-6 days between rolls, so I need to be choiceful about not rolling too often. If the market moves a huge amount in a couple of days, I may need to roll early, but then I’ll want to try to go longer before the next roll. The other thing to consider is that often the markets overshoot in one direction or the other, so I try not to move too far to chase moves that go on for days, and stay patient that the market will counter the trend.

If a position isn’t winning regularly and isn’t holding its premium in control, that’s a sign that the strikes aren’t right for the market and the duration. For a while I was trading 7 DTE Iron Condors on SPX with around 100 wide bodies and 50 wide wings. I would adjust nearly every day, but I couldn’t keep the position in the profit zone, and I often took losses. There wasn’t enough space in the body and the wings weren’t helping enough. By widening out the body and wings and adding more time, I found the position much easier to manage, and more likely to be profitable, and much less likely to take a big loss.

One way I can tell if I have a forgiving position is to compare my premium to the premium of the same position a few strikes higher or lower. For example, with Schwab StreetSmart Edge, I can pick Iron Condor as a strategy, pick an expiration date, pick a body width and a wing width. The application will then give me a list of strike combinations and premiums for those parameters. If all the choices around my preferred strikes have similar premium, then I know that price movement will have minimal impact on my chosen position. If there is a rapid change in premium for other strikes above or below my choice, it means my Iron Condor parameters are not very forgiving, and I should adjust time or widths or both. Other brokers will have similar ways to compare prices by shifting up or down all the strikes.

I have updated the earlier graphic to illustrate how a change in price over time will dictate the choice of a new position to roll to. The new price now dictates a new expected move, and new ideal strikes and expirations. Hopefully, this chart will help those that are fond of graphical illustrations.

roll down and out — After 7 days of mostly down moves, I decided to roll down my positions and roll out to a later expiration. In this image, the old position and expected move are there along with an updated expected move and new strikes.

Eight legs in the Roll

Since an Iron Condor has four legs, rolling involves closing four legs and opening four new ones. I don’t think any broker or exchange allows a eight-legged trade, so at a minimum this will take two trades to complete the roll. My preference is to roll the puts as a trade, and roll the calls as a trade. I usually start with the side that is being tested and might need a debit to roll to a new expiration and strikes. Then I do the other side, usually moving the same amount and keeping the same width, expecting to collect more to roll the untested side than I pay to roll the tested side.

At times, I may have a situation where I don’t have enough buying power to roll one side while the other side remains in place. If that happens, I’m probably using more of my buying power than I should, or the position is just too big for my account. It isn’t that big of a deal to manage the situation, however, I just close the untested side out and roll the tested side, then open a new position on the untested side. Worst case scenario, I can close the whole Iron Condor at once- freeing up its buying power, and then open a new one with the same buying power. As long as the wing widths are the same and the new Iron Condor collects more to open than the old Iron Condor cost to close, there should be a net gain in buying power. But again, any time buying power restricts a trade, it is probably time to pare down some positions in the account.

How Iron Condors tolerate price movement

Probably the best way to explain how an Iron Condor tolerates price movement is with an example. Earlier in this post I showed an opening trade from April 1, 2022. Let’s look at it again and look at how it fared after 7 days.

Notice that the premium collected is approximately $15 each on the put side and the call side.

Closing position — After a week, price has dropped to 4500, but the premium has dropped for a profit.

The premium on the put side has gone up to around 16.50, while the call side has dropped to just under $6.

So, after 7 days, the trade made about $800 on $10,000 risk, an 8% return. But, that’s just the start- the plan is to roll, and so the closing trade above was combined with the following opening trade:

new roll position — On April 7, this trade was opened while closing the old position for a net credit and strikes that are back at the edge of the expiration expected move.

The combination of closing the old trade and opening the new trade is a net credit of just under $14 premium. This is the result we are looking for- a profit on the trade being closed, and a credit to move out in time and get to better strikes for the latest situation.

And just to finish the example trade, let’s look out another week and see what happened to the market and the trade that was rolled to.

roll result — After rolling down, the market kept going down, but stayed within the new strikes with plenty of space to spare.

By April 13, the market had dropped even further, approaching where the puts from the original position had been. However, the roll down gave the new position plenty of space and the trade was sitting at a profit, and ready to roll again.

Closing the rolled position — After 6 days, the rolled position had decayed even after a market move. Again, puts lost money, but the calls made the position profitable.

This trade made $1430 in 6 days, a 14% return on capital. Since the market went down, the put side of this trade lost money, although not that much since the price didn’t end up that close to the put strikes since our new strikes were lower than the old ones. Time decay helped counter the price movement against the puts. The money was made on the call side through both price movement and time decay. In the end time decay, represented by Theta, eats away premium as long as price doesn’t get too close to the strikes.

These are examples of trades I did during the Spring of 2022 in the face of a bear market. Not every trade faired this well. Some market moves were too fast and too far for me to be able to roll before the position went too far to one side. But more often than not, this rolling methodology has kept me from having positions blown out, and keeps day to day portfolio value from varying out of control.

You may notice that the example trades shown here don’t exactly follow all the mechanics I’ve described. Since those trades I’ve become a little more likely to intervene early, although it’s a balance with avoiding over-adjusting.

Finally, I don’t always get my rolled positions re-centered, like I did in the example I presented here. Often, I’m happy to just move in the direction of the market and make sure my new strikes are a bit out of the money on the tested side. In this crazy bouncy market, we get lots of reversals, so I let my positions stay a little off when the market has moved a long way and technical indicators suggest the last several days move may be about finished. However, these choices come down to individual trader preference and market outlook. No one knows what is happening tomorrow or next week, so we each have to decide what trade is best based on the information available. For a real life example of this type of decision making in action, see my post on the Goals of Rolling an Iron Condor.

Good luck trading and rolling Iron Condors!

The August 5, 2024 VIX Explosion Impact

Personal Impact

The Perfect Storm of Fear

Unprecedented Changes in Implied Volatility

Margin impacts

Marked loss impacts

Position size considerations and notional value

Impact of the number of net naked options

Defined risk vs. Naked Risk

When the tide goes out, you find out who is swimming naked.

One time event, or regular occurrence?

(Without losing a lot of Theta decay)

Covered Call Trades

Stock Replacement Call Trades

Poor Man’s Covered Call Trades

Buying an Out of the Money Call Spread

The Call Back Ratio

Conclusion

Call Spread Set Up

Managing the Out of the Money Call Spread

Holding a Call Spread to Expiration

Folding with Limits

Continually rolling a credit spread

Why this Delta range works

Assignment Risk

Final Thoughts

4 risk levels, 4 underlying types

The Matrix

Covered Options

Buying options

Trading Option Spreads

Selling Naked Options

Bonus sections

Bonus #1 Ratio Style Trades

Bonus #2: 0 DTE trades

Conclusion

Changing to a full time “real” job

My new routine

Results

Things to know about 0 DTE

Selling options with 0 DTE

0 DTE Iron Condor

Iron Fly 0 DTE trades

Long Strategies for 0 DTE

Buy 0 DTE Straddle

Jump on the Trend with a Long Option

The Binary Event

Conclusion

Overview

What didn’t work and why

Short duration trades

Selling Calls too Close to the Money

Selling Options on Individual Stocks

What went well

Selling Long Duration Puts

Put Ratio Trades

Using Futures Options to Pump Up Returns

Selling Naked Futures Options

Using Research to Test Strategies

Rolling Spreads in the Study

7-10 DTE Roll

21-42 DTE

42-49 DTE

How to Use This Information

Final Take-aways on rolling put spreads

Example Iron Condor Roll

1. Neutralize Delta

2. Harvest profits from old position

3. Collect a net credit from the roll

4. Widen the body of the Iron Condor

Quadruple Crown!

The basic setup of an Iron Condor

My preferred Iron Condor setup

Managing the trade with rolls

Eight legs in the Roll

How Iron Condors tolerate price movement

Enjoy this blog? Please spread the word :)