When options hurt you

The past 2 years of my active options writing have been very interesting and reasonably profitable. In many monthly posts, I have asked myself the question how long it would last and what would happen when there is a correction. This is no longer a hypothetical question…

With the events of the last week, the markets in general are down and individual stocks can be down even more. What does that do to an option portfolio and how does that impact the feelings of an option trader?

The past 2 years

Results have always been good. Agreed, there was some learning money to be paid by going in big time on a market drop and using an instrument I do not understand well.

Other than that, the cashflow has been nice, especially expressed in a pct of the capital that I reserve towards options.


I also had to introduce the concept of elephants. These are positions are deep in the money and that I need to roll far out. That means that for months – sometime 12 months and more – there will be no profit possible. The reason that I do this is to avoid assignment. Remember, I do not want to own stock.

My portfolio should be able to make money no matter what the market does: going up, down or staying flat. Off course, there are limitations: an always win does not exists. This was my plan

Have positions that make money when the stock goes up or down

Have uncorrelated underlying stock: This way, not the whole portfolio should be in problem in the case of a market event

Limit myself to stock I do not mind to won

The portfolio before the events

Early January, I started to trade some positions that combine short puts and short calls: Iron condors and strangles. These positions will be profitable when the underlying stock does not move to much in either direction. And the fact that the option position can only be hit on one side (a stock can not be up and down at the same time) and has 2 written premiums, means that you have extra protection. These positions were very small in my overall portfolio. I tell myself each month that I need to do more of these trades, somehow, I fail at this.

Uncorrelated stock: I always carry positions in regular stock, ETFs, gold and oil. In theory, there is some “uncorrelation”

Worst case, When assigned, I end up with stock that I do not mind to own. That is the theory. I work with sector trackers and dividend paying stock or some serious growth stock

My portfolio is leveraged. That means that I have more total value at risk than that I have cash in my account. It is great for the returns, it is killing when things go bad.

Observations after drop

Almost all of my puts are ITM. 3 are not. Every other position is ITM. Some deep ITM. That hurts… It creates a risk of assignment. And due to the leverage, I can not pay for all these positions.

It seems that I have far to few positions that benefit from stable or declining markets. I knew this, never acted on it. DO SOMETHING ABOUT IT. Till now, I have tried it a few times and got scared when the stock went beyond my call strike. I now need to decide if I can deal with that or not.

Correlation is a fairy tail. My gold and oil positions went equally south. Part of that is the fact that I use goldmines. Gold itself was down less. Maybe a thing to consider… There is less premium gold, it held up better in the drop.

What is next?

For each position, I will need to decide on a management strategy. In most cases, I will do what you do with elephants: roll them and try to get out of the position, sooner or later.

Some positions are less than 5 pct ITM. That gives hope to manage myself out of the position in a reasonable time frame.

Others are 15 pct ITM. That will ask a lot of time and comes with an increased risk of assignment. Sadly, these are also the biggest positions that I have and they are way to big for my portfolio.

Lessons learned

Correlation does not help in a fire sales.

Diversification needs to come mainly from having short puts and calls. Learn to deal with it…

Keep powder dry and be patient to wait for the good times, like now. Sadly, I have no money available to write options now. And now, the premiums are really juicy…

No single position should exceed 20 pct of your portfolio


What have you learned?











9 thoughts on “When options hurt you

  1. Sounds very familiar. I was in a similar position but already a few months back. Made the decision to take the losses and stop trading options (and this really hurt!). I can’t stand the looming assignment and being ITM, it’s not in my character to stay at ease with this sort situation. I’ve got a lot of respect for people who can! I usually start to make dumb moves (something with emotion and the market, never a good idea). In short, I’ve decided to stick to dividend investing, ETF/trackers and real estate. Better fit for my person.
    Any how, good luck!!


  2. Well I learned where my pain limit lies investment wise. Unfortunately the drop blew past that limit and the market did not listen to my repeated use of my safeword. Lesson learned, the market is a cruel mistress …


    1. Cruel mistress… Well said… Even for people that buy and hold she now and then throws a damn hard curve ball… Then again, a savings account is like a frog being booked slowly…


  3. courageous that you report on your mistakes. These may be more instructive to others than all the “good news” posts. I would recommend that you read “the way of the turtle” (Curtis Faith) or any other books on the “turtles”, jn particular on the trading rules and risk management tools that were applied while trading different markets. It’s not specifically for options, but for all futures markets. It has good principles/rules on diversification across asset classes, cutting losses, let profits run, and it’s an interesting story (it’s not the best book on trading systems and portfolio management, but it’s a great read). In any event, consider this little correction as a warning sign, and make sure you don’t blow up when the real crash hits.


  4. I’ve been trading options now for well over 15 years and based on your post I am 1,000% sure you’ll be fine. You did what most never do, face the truth. I can tell you that I used to suffer the same fate until I asked myself these questions…

    “Is there a lower risk way to accomplish my goal?” OR “Is there an easier way to do this?”

    For years I sold Puts a certain way because 1) that is how it was taught to me and 2) because everyone else does it this way.

    But once I started “constantly” asking myself those questions it caused my brain to come up with all kinds of different ways to do the same thing.

    I say all of this because of your one comment, .”I hope i can cope with it going forward.”

    As a fellow options trader I will say remove the word hope from your vocabulary. Instead, devise a strategy you can emotionally cope with both in good and bad markets.

    I hope this doesn’t sound preachy…I’m glad you shared and my heart goes out to you. Again, I’m sure you will be fine and I look forward to seeing more of your success.


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