My situation is kind of weird because I don't know when I'm going to retire. Could be in 20 years or could be tomorrow. Since I became self-employed around 2016, I decided I will never go back to a regular job. Luckly the business has done well, and I have been saving most of the money. If/when this business is no longer viable, I need to be ready to retire. Until then I have no issue doing this indefinitely.
However, because I don't know when that day will come, I feel like I have way too much cash. Then when I finally decide to move some more into my investment account I feel the market is crazy and going to crash any minute.
I do have it set to move a certain amount automatically every week or so, but still would take a looong time to move a significant amount. If this crazy market ever goes down I plan to up that significantly.