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My biggest regret is not saying no when I should have said no. I married young and left too many spending decisions to my spoiled first wife. If I had invested instead of paying credit card interest, I likely could have retired at age 55.
Investing in a wrap account with front loaded high fee active funds. Luckily I think the true cost was limited to 10-20K. This kick-started me down the path to self-directed investing. The day I transferred the last $ and closed that account was a day I celebrated.
I tried to get too cute with investments and risk in the early 2010s. I had most of my money in low-cost index funds, but I also kept too much cash considering my still modest net worth and rising salary. I should have just parked it all in a target-date fund and not bothered tweaking.
Nowadays, I have more in cash and bonds since my net worth is higher (I’m sort of near that point where I have ‘won the game’ so why get too risky?) and my salary is a lot lower since I don’t have a 9-5 job. And my current profession is really correlated to how financial markets perform. So it makes more sense to not be all-in on stocks despite me being just 33yo.
I think a lot of us dialed back risk too much right around 2010. I had good reasons, but the main thing I confirmed is that my risk tolerance is indeed fairly high (though I’ve dialed it down a little as I’ve aged.)
Spending so many years trying to be a stock picker instead of an index investor was a big mistake (as was selling AAPL back around 2001).
My biggest financial regret is that, I worked hard for money but didn’t let the money work as hard for me. How? Because I remained un-invested in stocks for the entire first half of my career.
It wasn’t due to lack of stead income or good money habits, but lack of financial literacy and investment knowledge. I saved quite a bit, but left the money in CDs and Bank accounts.
A small example of my goof-up: I started my current job in early 2000 and was contributing only a small amount to my 401k. It was the default option during initial enrollment. The money was invested in a conservative mutual fund. I don’t recall why I chose that one, but most probably because it was the first one in the list. Anyone with basic financial knowledge would’ve made full 401k contribution in my situation and invested aggressively. Well, better late than never!
My entire life I have been a saver and a planner. I’ve made decisions, like not attending sporting events or other fun activities, purely to maintain focus to my studies and “getting ahead” by reading books, attending additional classes, etc. My biggest financial regret is not allocating more time and money to experiences and being so relentlessly focused on saving and advancing in my career. A little more fun along the way wouldn’t have hurt.