As someone with a lot of cash on the sidelines, I’m not afraid of losing the value since I know that it will go up long term. But the question is, so I buy a bunch of stock now, or do I buy it when it’s down 50% from where it currently is. Say I’m in SPY 100% at $200k. If I do it now, maybe I have $220k in 5 years. If I do it after stocks are down 50%, then maybe I have $440k in 5 years.

Obviously I can’t time when the pullback will start and end right now, but in my experience it’s pretty easy to tell when it’s happening because of the overall sentiment online and in the media. People are emotional and almost everyone lacks meta level awareness or foresight.