Options trading update – September 2021 – covered calls

September options trading review

This month I received $1,346 in premiums from selling options.


Altogether I have made over $6,000 selling call and put options in my non-registered margin account.

The more options I trade the easier it becomes to manage larger positions. 🙂


September trading breakdown

Here are some key points from this month.

  • I sold 14 options. 4 Calls and 10 Puts.
  • My total trading commission was $24. Higher than usual.
  • All options that expired in September were out of the money. Nothing was assigned. 🙂

Below is a table summarizing my transactions. (Source data from IB here.)

  • Initial underlying price – The market price of the underlying stock/ETF when I made the options trade.
  • Price difference % – How much the underlying will have to rise or fall to be In-The-Money (ITM).
  • Initial days to expiry – How many days remain until the option expires, from the day that I traded it.
  • Initial Delta – Measures the initial probability of an option expiring ITM. eg: if a put option has a Delta of -10%, there is a 10% chance it will be exercised, and a 90% chance it will expire worthless.

September 2021 options premiums

As you can see in the right-most column, most of my options have a low chance of being assigned.

To my pleasant surprise none of my options have ever expired in the money before. *knocks on wood*

However, ContextLogic (WISH) currently trades at $6.02/share. That’s just barely above my $6.00 strike price.
So there’s a fairly good chance I will own WISH stocks when my put option expires 18 days from now. 😅


Call options – A thorough explainer

As you likely know by now my primary options strategy is selling naked Puts. 😉

That’s why I enjoyed watching the stock market fall last Monday, posting its worst daily decline in months.


But I also earn money from selling covered calls.
I uploaded a new video yesterday breaking down how that works.
And I used some of the call options I traded this month as real world examples.

I sold a call option on TD Bank to reduce my concentration risk.
TD.TO is currently worth 11% of my portfolio with Interactive Brokers.
My goal is to trim this down to below 10%. But rather than sell some TD shares at today’s price, I can potentially sell them at a higher price in the future via a call option. 🙂

I sold call options on Canadian Natural Resources (CNQ.TO) to take advantage of its cyclical movement.
Yes. This is considered “market timing.” I know that’s a big no-no in the personal finance community.
But since when do I follow rules? 😂

I explain each trade in more detail, and demonstrate how I earned $142 in premiums that day.
You can watch the video here, or see below.


Don’t want to spread myself too thin

Last month I experimented with a put spread. Both related contracts have expired worthless as expected. 🙂

Spreads limit the downside risk in case a stock drops sharply. But they also reduce the premiums earned.

After some consideration I have decided it is more important to maximize my premiums than to have the downside protection. I don’t mind being assigned a stock at a higher price than the open market. I trust my due diligence process. If I decide on a $100 strike price, it means I believe the stock is intrinsically worth at least $100 even if the short term market conditions don’t reflect that value.


Experimentation + reflection = progress

If I try something new and think it’s useful, I will incorporate it into my larger financial plan.
And if I don’t think it’s a good fit, I will drop the idea but maybe revisit it in the future.
Keep what works, and discard the rest. Put spreads is an example of something that doesn’t work for me.

My investment process constantly improves by making small, intentional tweaks over time.
I always want to be learning, and trying new things, while maintaining control over my portfolio.

Next month I’m excited to experiment with the short strangle. It sounds like a quickly executed wrestling move. But it’s really just a way to profit from little to no movement in the underlying stock. I look forward to share how that goes in October. 🙂


Random Useless Fact:

According to Greek mythology there were a total of 12 Olympian gods.


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09/27/2021 6:17 pm

I’m certainly not trying to criticize you as clearly you are making money in the market. Just trying to understand better your overall strategy with this. It seems like you put up a lot of potential margin if all your options got assigned vs your gain. In your usd account, you would need over $100k usd in margin or cash while getting about 0.7% return.

09/30/2021 3:00 am

I think the strategy is sound. I question the companies you are choosing to use the strategy on. A company like Tesla moved from ~$580 to over $700 in a month or so. That’s a 20% difference. Owning the stock would have generated that. Of course it could have gone down just as much or more in that time frame. I guess you also wouldn’t get the options premiums either on certain companies.

09/28/2021 7:04 pm

This is such an interesting strategy because in a way it’s both more safe and more risky than conventional margin investing.

For example, had you just invested $60k of your available margin into SPY you would have earned about $12k so far this year, which is similar to what you’re earning with your option trading strategy but with a lot less effort.

By instead selling PUT options, you’ve reduced your risk as you would still earn that approximately $1k per month if the market went sideways for the year instead of up 20%. On the other hand, you’re increasing your risk because you are putting up twice as much margin. You are also potentially less diversified because you’re selling puts in only few individual companies at a time.

Overall, I’m loving this series and am happy to see you’ve found some success with this strategy!

09/30/2021 12:50 pm

Hi boss,
I am curious. do u prepare 150K cash to take over the stocks if all put were assigned to u?

10/08/2021 2:15 pm

Welcome to the world of selling options! I’ve been laying low… need to start up on it again!


[…] again none of my options have been assigned in October. However, I have a couple of call options sold in September that are currently in the […]