A really interesting thing happened in March 2020. The market crashed and we all remember how gloomy everything looked. Needless to say, some businesses were going to be directly affected by Covid (eg: travel, hospitality) and their stocks went down as much as 80%. But it also became clear that many stocks were just collateral damage (eg: most of the tech stocks), and that they were going to recover more quickly than others. I bought all the tech stocks I could and things worked out great. If anything, I gave myself too much time to execute on this strategy - as a way to protect against the market tanking even further, I decided to dollar-cost average and make my investments over a 6-week period between mid March and end of April. As is obvious in hindsight, the mid-March cohort outperformed the late April cohort by a wide margin. Writing about this in April 2021 doesn't seem so surprising, but I can tell you that in April 2020 I was shocked how fast the market was improving even though the global news only kept getting worse and worse. I am close with many people who run their own businesses, and many of them had their worst weeks in April. I guess the market was recovering following the same rationale that I used, so I shouldn't be too surprised about its behavior, but it was still interesting considering how my risk profile is so different from the majority of other people.
Would I recommend timing the market? Most of the time, no. But a lot of people talk about the impact of the 10 best or worst days in the last 20 years, and I would say those "insane periods" do exhibit somewhat recognizable patterns that makes it possible to identify them and take advantage of.