I am mid 40's and have invested in index funds for around 10 years. I have bought shares of VOO for $205 before. When VOO hit $500, I slowed down a little and eventually it went to $550. I have a HYSA with 100k which everyone told me Im trying to time the market and losing value by not having it in there. Well I am the rare story of how timing the market worked out by luck. I would be down five digits if I put it in at the too. I just transferred the money over to brokerage and if you were me, would you shove all 100 now, or keep trying to time the market and hope it goes down more? If it shoots back up and Im stuck with all the cash, I will be sad