I've been kicking the heck out of myself for paying off my law school loans within 3 years of graduating (payoff ca. 2014, graduated in 2011, had about $160k of loans) rather than investing everything I had in the market. Sofi and its progeny didn't exist yet when I graduated--they didn't really get going until I was pretty close to fully paid off--so I was looking at 6.8-8.1% loans, but man, the amount of money that decision has cost me.
I've been kicking the heck out of myself for putting a $120k downpayment on a house in 2016 (pre-election) (20% downpayment). It was a bit more than I intended to spend on a house, but not by a ton and it has everything I want in a house for the medium-long term. But man, the amount of money that decision has cost me.
What's the common thread between those two things? Doing both (other than going about $20k higher on downpayment than I had planned on) was "in the plan." So it hurts in hindsight, but so does the fact that I didn't put $20k into Bitcoin back in 2012. I had my mouse pointer over "buy." I couldn't go through with it... it wasn't anywhere in my plan and it felt totally speculative (because it would have been). Talk about hurting in hindsight.
But you know what decisions tick me off the most?
-In 2016, post-election, although I fortunately did not sell what I had in the market, I was slow to invest in the market with new funds. I figured, Trump is a maniac, there's no way we don't have a near-immediate crash. Thank goodness I didn't have the full courage of my convictions on that and didn't liquidate all of my holdings. I had my mouse pointer over "sell."
-In 2017, I took a chunk of my 2016 bonus and made a $26k extra payment on my mortgage (I invested most of the rest, and held $25k in cash to buy a car for the first time in 10 years). Again, I just couldn't swallow what the market had done post-election. So, that lost me a fair amount of money. (Of course the car is also a catastrophically expensive thing once I factor in foregone investment returns on that money, but I made the decision not to think in those terms and to allow myself that lifestyle creep.)
Common thread? They were decisions outside of my plan.
But good thing about them? Further reinforced the fact that my "gut" doesn't know jack-all. So. I'm highly confident the market is going to crash at some point in the next couple of years. I believe that my party of choice will probably help a market correction along when they come back into power by increasing taxes, Trump is still nuts, and we're overdue. And I still sent 100% of my 2017 bonus into the market (after taking out taxes, funding anticipated medical expenses for the year, etc). I wasn't in the workforce or the market for the dot com bust or 2007-2009--wasn't in the workforce until 2011 and was minimally invested until 2014 because of my focus on student loans--but I'm hoping that these two frustrating occurrences of market timing gone wrong will stay in my mind and keep me from selling when the correction does come.