Allison, thanks for reading and leaving a comment. I keep a parallel paper account where I purchase the SPY on the same day with the same amount of money every time I contribute to my brokerage account; this was 14 separate transactions across 2020. Only about 20% of my contributions were made in March when the S&P was very low (the numbers you give above would require 100% of your investment to be made on 3/20, which usually only works in hindsight). This is the best comparison for what I am doing vs. just buying the SPY. Based on that, my efforts in 2020 were significantly ahead of the S&P 500 (20% margin).

However, that gap has narrowed in the past few weeks as the S&P 500 has taken off again (I’m down to +/- 5% higher annual return as of today, which is still a significant improvement over the index). We’ll just have to see how it goes moving forward. Investing is a long-term game, so it will take a few years before I’m able to establish a track record to know if what I am doing is worth the effort or not (ie, can I keep beating the S&P 500 or not).

I agree that most investors will do better just sticking to the index, but I’m interested in putting in the extra effort to see if I can do better.