top of page
  • Writer's picturethemoneyloaf

Reaching 100 profitable trades in 2022

This week's article will be a little different from most weeks. There's not much going on in the markets now and I'm sure you're bored of reading the same updates in SCHD and WBA, so I'm going to skip that this week and talk about what's going on in my overall strategy and combined portfolio. This week:

  1. Reaching 100 profitable trades in 2022

  2. Assignment in VOO - intentionally

Let's go!


100 profitable trades in 2022

Yep that's a huge milestone this year, hitting 100 profitable trades in 2022 with year-to-date realised profits reaching $18,076. Assuming the trend continues, I should end 2022 with about $21,000 for the year - not too shabby for a year where the S&P is down 25%. The main reason for the high number of trades and profitability is mainly the volatility this year, but also being disciplined in taking profits. I've mentioned a number of times in these newsletter that I've been taking profits early and aggressively, I think that's helped with building consistency and wins. The second reason is probably focus. I've made 111 trades this year, but they've all been focused on only 24 stocks and ETFs, out of maybe 35 underlyings on my watchlist. When you know you've picked the best stocks to sell options against, it provides a level of confidence to keep selling options even in volatile, down markets, and also the reliability and consistency of continually entering and exiting the same positions throughout the year (more on this in my VOO assignment later). I thought I'd also put the 100 winning trades in context of my total number of trades in my portfolio. These numbers are current as of 21 October 2022.

First of all, a 90% win rate is pretty good, though still a little low than I'd like. Next, the market's downward trend and volatility has also led to higher assignments than usual. My average rate for the 4 years spanning 2018 to 2021 was about 2%, so 4% is much higher than usual. However, at least this year, that has been part of the plan, which I'll elaborate on in a little more detail in the next section.


Intentional assignment in VOO

Since May 2022, I've been trying to pick up shares of VOO (the Vanguard ETF tracking the S&P 500), but of course, I'm not going to pay market prices for it.

My first VOO trade was on 18 May, when it was trading about $360.

I started selling cash-secured puts in VOO every month or so, collecting a total of $1,343 in realised profits from closed trades.

No streak lasts forever, and I finally got assigned 100 shares of VOO on Friday, at a strike price of $355, but not before collecting another $945 on that trade on the way in. After taking into account all that premium, my cost basis on VOO is $332.12, or close to VOO's lows for the year. Way better than just buying VOO in May at $360. As my goal is to build a long term portfolio, I view selling puts every month as a way of dollar cost averaging into a position, setting my own price to buy shares, and waiting for the market to meet me at my price. For a lot of people new to selling options, getting assigned is probably their biggest fear - I get this question/email almost every week. I hope this example in my own portfolio shows you that an options seller is better off selling options and getting assigned, rather than buying the stock outright. And I haven't even started talking about covered calls.


That's it for this week, I hope you don't mind the different format. Hopefully the market will throw some opportunities my way next week - I need to load up on more positions!


This article is for educational purposes only. This is my own portfolio which is being managed according to my goals and risk tolerance. Your situation is likely different and you should do your own due diligence before investing in stocks or options.

bottom of page