Why I Avoid Expiration Week

As I interact with options traders (mostly online), I see the topic of expiration come up quite a bit. I see lots of questions about what happens when options expire, especially in the money options. While I think it’s good to understand the terms and conditions of options contracts, I do not believe it’s usually worth putting oneself in the position where expiration is going to be a problem. In fact, I not only avoid expiration day I avoid expiration week and will explain why in this post.

Exceptions to the Rule

Before getting into why I don’t like expiration week, let me say that much of this has to do with how I trade. I’m not saying that every strategy, or even every successful strategy should never go to expiration. There are perfectly good strategies that expect to take contracts to expiration. One such strategy is known as the Wheel or I’ve seen it called Laddering. The idea is that you sell cash secured puts on shares you wouldn’t mind owning. Then if you get assigned, you sell covered calls against those shares at a price you already like. While this isn’t the way I trade, it’s a perfectly good options + stock strategy. But notice, I said “+ stock”. This strategy explicitly plans to own stock at some point in time. If a trading plan includes this, then going all the way to expiration is perfectly acceptable and, perhaps, even desirable.

Another example could be a vertical spread that is very far in the correct direction that going to expiration yields maximum profit and the risk of losing is very low. In this scenario, I would prefer a credit spread so that everything expires worthless and there is no assignment mess but it can work with a debit spread. While this carries a bit more risk than the wheel, it’s reasonable under these conditions to go to expiration.

There may be other exceptions to my rule but these are two off the top of my head. But now I’ll talk about why I don’t like expiration week.

What I Don’t Like About Expiration Week

If you’ve followed my trading videos at all, you know I like to trade non-directional spreads on large indexes (usually SPX). One of the many reasons I like doing this is that I don’t like picking direction and I don’t want shares (SPX is cash settled since there are no shares unlike SPY). There are occasions when I may trade an underlying that is share settled but, in any case, I have no desire for shares of stock in my options account. It’s just not part of my strategy. Because of this, expiration day and even expiration week cause more headaches than they are worth.

High Delta and Gamma

The main reason I don’t like expiration week with the types of trades I put on, it’s almost impossible to stay non-directional which is one of the main goals of my trading. I trade mostly calendars and butterflies which both have expiration graphs that look like tents. In fact, in my videos you’ll sometimes hear me refer to the tent of the trade. But for most of the trade, the T0 curve, which reflects today rather than expiration looks nothing like the tent. See an example below:

A 24-day Calendar on day 1

This is an example of a 24-day calendar which is a typical trade I’ve been doing recently. The shorts are 24 days away from expiration while the longs are 5 days away from the shorts. The dark blue “tent” is the expiration graph the light blue arch is the T0 line which represents the risk today. Note the difference between the two risk lines. As the trade gets closer to expiration day, the two lines will converge, slowly at first but very rapidly in the last few days. Note the slope of the T0 curve. It’s quite flat and manageable and I would consider this trade reasonably non-directional. And the Delta and Gamma values reflect this as they are both very low. As the underlying moves in either direction, the effect on the position is not very much, at least until you get outside the tend at which time the slope starts to get steeper. However I have a reasonable amount of time to manage the price risk as the tent covers about 2 standard deviations for 1 day. The odds of this trade staying in my tent in one day is around 94%. Not guaranteed to be sure but pretty good odds and even if it does go outside the tent in a day, the odds of not getting a chance to manage the trade is even lower. This is a pretty manageable trade, in my opinion.

Now let’s look at the first day of expiration week:

A 24-day calendar on day 20

So this is a theoretical view of that same calendar on day 20 (the Monday of expiration week). Now the change in the T0 line is much more apparent. On the one hand, the profit potential if the underlying stays in the tent is very good. At the center I can double my money. But look at the slope of that curve and the corresponding delta values. Delta gets very big, very quickly and moving much to either side of center can get this trade into trouble very quickly. This, to me, is no longer a non-directional trade once it moves even a few points from the strikes of the contracts. While the potential reward is great, the price risk is too high for me. Take a look on Thursday of expiration week:

A 24-day calendar 1 day to expiration

Now the two graphs are almost aligned which makes sense since expiration is 1 day away. But looks that the Delta values as you get away from the strikes. They get into triple digits very quickly. But also compare the corresponding Gamma values on the 3 charts. The high Delta change rate is driven by Gamma and Gamma is exploding during expiration week. This is why I refer to expiration week as “Gamma Week” because Gamma is driving the risk. Is there a big profit potential? Of course. But it all can vanish very quickly with a decent move and we still have another day in this trade before expiration.

Perhaps your thinking, well that’s just a calendar, what about a wide Iron Condor? Sure, you may get more room on a high-probability Iron Condor. But as expiration approaches, you run the risk of taking a max loss on the trade and the wider you make your Iron Condor the less credit received and the lower the reward for the risk being taken. Can they work? Sure. But you need the stomach for the end of the ride. For me, the risk/reward of wide Iron Condors is not attractive.

Assignment Is a Hassle

Just my opinion here, but dealing with assignment scenarios when I do not have the goal of buying/selling the stock is just not worth the hassle. As you saw in the above example, the risk/reward gets crazy but in addition to that, there can be assignment fees which can cut into the profits as well as tying up capital to squeeze out those last few dollars out of a trade. Taking all of that into considering, I’d just rather avoid it altogether.

Avoiding Assignment

Fortunately, avoiding assignment is relatively easy. Assuming the underlying is settled in shares, you can avoid assignment in almost all cases by doing the following:

Close Before Expiration

This is the most obvious one. Just don’t be there when expiration happens. Take most of your profit and move on to the next trade. If your position isn’t open, you can’t be assigned.

Be Aware of Dividends

While most underlyings are “American Style” which means they can be assigned at anytime before expiration, this rarely happens. The #1 reason this does happen is dividends. If the dividend is worth near or more than the extrinsic value on your short calls, there’s a good chance the shorts will get exercised and the shares will be called away at or near the ex-div date. The good news is that the dividend amount as well as the ex-div date are public knowledge, so with some planning, it’s easy to avoid this situation as well. Don’t have a short position on if there’s a reasonable chance someone would want to buy the shares to collect the dividend.

There are some rare cases that you can’t always anticipate. The only time I’ve had shares called away early was due to an acquisition. I sold some calls against some shares I owned and the company was bought by a larger competitor at a good premium. My shares were called away the very next day (it was announced after the market closed). In cases like these, there may not be much you can do to avoid early assignment. But fortunately, this is very rare.

What Do You Think?

So, this is why I don’t like being even close to expiration. It just doesn’t fit my style of trading. That doesn’t mean it’s wrong on all occasions, but I think it’s important to understand what can happen as trades enter Gamma Week. I see traders worry about what will happen to their trade if all or part of their trade expires in the money all the time. I agree it can be confusing, especially to newer traders. So unless your trading plan includes assignments, just avoid it. Thankfully, avoiding the various expiration scenarios is quite easy to do.

So, that’s my take. As usual I’m always interested to hear what my audience thinks. This is a place for learning and discussion options. So feel free to ask questions, make constructive comments, or start a discussion.

Until next time….Good Trading!

Midway Mail: Questions on My Calendar Setup

I always say I enjoy getting questions and fostering discussions and while I have been getting some very good feedback, I have found some questions that I think can be better answered in this forum than in email. I will keep the viewer anonymous, of course, but I think many traders out there could benefit from my answers and even come up with other (better?) ideas as well. I’m here to learn just as much as anyone so maybe someone out there has some better ideas and I’ll change my mind. All good stuff.

The viewer has some questions around the calendars I put on over the last few months. If you aren’t familiar with Calendars, check out Episode 13 my Options Fundamentals series. It should give you the basics of the trade and how it works.

Question 1: Why do my calendars more often than not start on the call side?

This is a great question and there isn’t one correct answer for everyone with respect to which side to use when setting up a calendar. When considering this, the first thing to determine is why you want to put a calendar on in the first place. This seems obvious, but I’ve seen lots of new traders put on trades without knowing why. There are traders who put on calendars to get a cheaper long call or put. They really want to be long a call or put but want to sell something against it to help pay for it. In this scenario, the ideal situation would be for the short to expire worthless leaving them with just a long call/put at a cheaper price since they got to keep the premium from the short option. In this case, it really matters which long option you want to have if the trade is successful. You really want to be directional, so you would choose the direction you want by choosing calls or puts.

However, that is not why I put on calendars. I am not a directional trader (outside of a rare speculation play) so for me, calls or puts isn’t nearly as important for my calendars. The reason I put on a calendar is that it is positive Theta and Vega and there times when I want those factors working in my favor. I almost always like Theta to be positive as I prefer time to work in my favor, but if the volatility of the underlying is low, I would rather be long volatility when trading it. I believe fundamentally that volatility is mean reverting, meaning that it always returns to the average. So when the volatility of my underlying is low, I would rather be long volatility since I believe it will go up. Conversely, when volatility is high, I like to be short volatility (negative Vega) since I believe it will go down. Of course, I cannot know how long it will take for this to happen, but the idea is to set up my trade to have the best chance to be helped by volatility. Since I also have time working in my favor, I can profit from that even if I don’t get the volatility move I expect, it just may take longer to get to my target profit.

Now that I’ve explained my goals of a calendar, I’ll try to (finally) answer the question. The answer is that, for me, it doesn’t really matter whether I start my standard at the money calendar in calls or puts. I intend to take it off as a spread so I’m not worried about which long I will have left. So how do I choose? I look at the open interest of the calls and puts that I intend to use and I pick the side that has the larger overall open interest.

So what is open interest? It’s a count of how many open positions exist on that particular option. It doesn’t matter if that open position is long or short so long as it’s open. This statistic gives us an idea of the liquidity of that particular option. The more open positions, the more interest there is in that particular option, the better the chance of getting good fill price with little to no slippage. Again, there are no guarantees here, but the idea is to put on a trade with as many factors in its favor to succeed. So if I have time on my side, potentially volatility on my side, and good liquidity so I’m not paying up for the position, I should have a better chance of success. Of course, price risk is always there as a calendar has risk on both sides as it’s a range-bound trade. But as I always say, this market pays me to take risk so there will always be risk somewhere.

So why did I end up choosing calls to start my position more often? Because during that time, the market was trending up which made calls more popular than puts. There could very easily be other times in the market when puts are more popular. So the preference for calls simply resulted from more open position in calls most likely caused by an upward moving market.

Let’s take a quick example. Let’s say I wanted to put on a calendar in SPX right now (note: I would not do that as volatility is too high, but this is just an example). I’ll do my usual shorts about 24 days out and my longs 14 days later (more on that later). Let’s look at the open Interest of each of my options:

Open Interest on shorts of a potential calendar

So, let’s assume I want to set up a calendar at the 3300 strike. So I choose 24 days for my short, and compare the open interest in the calls and puts. As you can see, the calls have a large advantage. But let’s also look at the options 14 days later.

Open Interest on the longs of potential calendar

So, in this case, the puts have a slight advantage over the calls. But it’s not enough to overcome the advantage of the shorts so I would start with calls here. It turns out today was a large up day so, again, it’s not surprising that the nearer term calls had such a large advantage.

None of this is to say that choosing the puts would be bad or wrong. Remember that using calls or puts doesn’t really matter to my calendar since I’m not worried about keeping the longs. And if I were to adjust the trade, I would most likely put on another set of calendars and I would use the puts for that to help keep my two calendars separate.

Question 2: Why are your calendars 2 weeks between the legs?

Another very good question and, again, there isn’t a perfect answer here. This has become a matter of preference for a couple of reasons. The first is this is the way I was originally taught to do the trade so there is some bias there. But, I keep doing it this way as I like the balance I get of risk and reward. All trades have risks and rewards and that ratio can be adjusted based on how the trade is entered.

As a quick reminder, a calendar is where I sell options and buy the same number of options at the same strike at some point later than the options I sold. It is this structure that gives the calendar it’s characteristics of being long Theta and long Vega. Why? A nearer term option has faster time decay than the same option further out in time. And in a calendar I am short the nearer term option so that is what gives me my time benefit (positive Theta). To get positive Vega, I buy my longs further out in time. Options further out in time have more volatility risk and since I am long the option that is further out in time, I get a positive Vega position.

So how does distance between the strikes affect the Greeks of the position? The further the distance in time between the legs, the greater the difference in the rate of time decay and so the result is more positive Theta. Similarly, the greater the distance in time between the legs, the greater the difference between the volatility risk and so the result is more positive Vega.

So why would I only choose 14 days? Surely, it would be better to increase the distance between the legs and get really high Theta and Vega working for me, right? Of course, there is no free lunch in this market and the price to be paid for having a large distance between the legs of a calendar is … price. In a calendar I am buying the further out option which has more extrinsic value (time and volatility) while being at same strike. This means that the greater the distance between the legs, the more the price of the longs will be compared to the shorts, which yields a higher debit for the trade which, in this trade, is my total risk. So I have to pay for the extra Theta and Vega with money from my account because the trade is more expensive. Let’s look at two examples:

A 24 day calendar with 1 week between legs

In this example, I have a simple calendar with the short 24 days out and the long 1 week later. This gives me 6.77 Theta and 46 Vega and will cost about $900. Now let’s push the long out to 6 weeks from the short:

A 24-day calendar with 6 weeks between legs

So this the exact same calendar but with the legs 6 weeks apart rather than 1 week apart. Here I get 32.84 in Theta, and 191 Vega which is much longer for both. But the cost of the trade is now $2726. So I have to spend about 3x more in capital to get the boost in Theta and Vega. That may look like a bargain, and there’s nothing wrong with taking that trade, but remember that Vega is a 2-way street. While it will be great if volatility goes up on this trade vs the 1-week trade however, if volatility goes down, I get hurt that much more as well. The other risk to consider is Gamma risk. While my deltas on these trades are similarly small, the Gamma is higher on the 2nd trade. While Gamma starts out small on both trades, the it will move Delta faster on the wider trade than the narrower one. This increases my price movement risk in a live market even though Delta starts off very neutral on both trades.

The Choices are Yours

I say all of this to say there is nothing bad about either trade as long as you, as the trader, understand the risks vs the rewards. There are many ways to set up a calendar to make these risk decisions. It’s up to the individual trader to decide what risks are worth taking versus the reward of the trade succeeding. A blog post is not the place to cover all of those possibilities but I did want to address the specific risks as it related to the questions asked. I hope this helped clarify what I’m doing as well as get you think about how to set up your trades.

Thank you again so much to the viewer who asked these questions. And I am very open to further questions or thoughts on anything on this site as well as trading in general. Feel free to follow-up here on the blog or reach out to me directly at midway@midwaytrades.com.

Until next time….. Good Trading!