Ask HN: How to deal with financial regret of what could have been?

> While I made some money selling (2013), it was just enough to pay off my loans, buy a place and invest a bit but nothing close to its current valuation.

I bought my first Bitcoins around 2011 and did a little bit of trading and ordering pizzas and whatnot early on. I think cumulatively I may have had about 60 Bitcoin over these last ten years. Early last year I sold the last ones to get a nice apartment. So in some ways I'm in a similar situation, though I would "only" have about a million Euros if I cashed out now vs. your 100 million.

I don't have regrets about buying pizzas for prices that would now correspond to extra rooms to my apartment or whatever: If we early market participants hadn't been willing to spend Bitcoin and to sell it off to other traders, there wouldn't have been a market, and the project would have died. Interested parties wouldn't have been able to get Bitcoin, the infrastructure around it wouldn't have developed, and the price today would be zero. We took one for the team, and we both did profit from it nicely as well. Yes, others profited more, but that doesn't keep me awake at night.

What I do have regret-like feelings about is selling around March-April last year, in the middle of a local minimum. Waiting until now, in hindsight, would have netted me close to 5x the returns, but it seemed highly implausible at the time. And I'm happy with the place I bought, even compared to significantly more expensive properties I see on the market.

Um, I have no real conclusion except I can relate to how you feel. I find my job interesting, but often tedious, and am looking forward to saving up and hopefully being able to retire around age 50-55. Hang in there! And yes, therapy/mild antidepressants are good things to try. Good luck!

> at one point would be just north of 100 million USD

What a fatuous remark! It's one thing to have junked a painting that turned out to be a Rembrandt, or let your one true love "get away."

It's another utterly banal thing to have closed a market position in a liquid commodity. Your having closed it in 2013 is just as unremarkable as your "losing out" on any number of bets you could make *today* which would result in 100M in profit a year or even an hour from now.

This is a good way of looking at it. I had ample opportunity to buy GOOG and AMZN early on. After all, I had a brokerage account, and I followed those stocks. I bought LVS at the absolute bottom, but didn't hold. As for bitcoin, I was mining in 2011. But then I soon decided mining wasn't worthwhile. I could look at it like, so close but no cigar. But really, none of those decisions were wrong or stupid. Hindsight isn't just 20/20. It's useless.

The way you retrospect about past positions suggests a general misunderstanding of the nature of market exposure. Noobs like OP have an irrational notion that it's somehow a "feat" to have taken on a btc position as if only a chosen few were given the opportunity to do so. It's a lot like telling your buddies "There was this hot flight attendant, and I almost asked her out." Almost doing it = Not doing it.

I think his situation is I asked the hot flight attendant out and she said yes and she was the love of my life and I dumped her. And she just invited me to her wedding.

> I know the answer on some levels is therapy. Is there any other advice besides get over it and therapy though?

A third approach is to acknowledge that, indeed, if you could predict the future, you’d be fabulously wealthy, but there’s nothing different about this example than any other one. If you’d purchased Tesla in January 2020, you’d be up about 8x, if you bought call options on X in Y, etc. The fact that you owned Bitcoin at one point doesn’t make it any more or less applicable, since you could have bought it at that time anyway.

If you want to beat yourself up over something, pick a decision that had a positive NPV at that time, not a decision that requires seeing the future (like this one).

That's a pretty specific situation you're dealing with so I don't know if I have any useful advice to offer. I can just say that throughout most of my life I've dealt with regret the same way, no matter the circumstances. I remind myself that it's a stupid and useless emotion to indulge in, since there's no way to go back and change anything. I tell myself "acknowledge things you regret long enough to learn whatever lesson was to be learned, and then forget about it."

Of course that's sometimes easier said than done, but replaying that thought in my head usually helps.

I think that's the key what lesson(s) did you learn. No point in worry about something you can't change.

The strict rule I adopted for myself is: when you buy something, you won’t be able to sell more than 50% of the position for 10 years.

This makes me rather conservative, and I mostly end up buying VTSAX.

I have Bitcoin that I bought in 2014, and sold 50% of my position in the bull run of 2017. I cannot sell any until 2024, even if I’d probably benefit by selling some now :-)

Sticking to this rule helps minimizing regret. Obviously it won’t completely catch investing in AAPL early etc.

Hindsight is 20/20. Try not to judge your past actions with current knowledge, that's simply unfair.

The question is did you make the most of the information you had available at the time? If yes, then there is nothing else you could have done. You couldn't have acted differently since you couldn't have known what you know today.

If no, then try to learn from the experience and move on. You can't change the past so no point in dwelling on it.

Just let it go, I came across bitcoin when it was valued at 5-6 Cents, I had spare $500 and wanted to long-term invest $100 into it, I even created my cold wallet, But later it slipped off of my mind and I lost opportunity of having 1500+ BTC.

Do I regret ?, I don't know.

I just let it go.

I have >200 bitcoins locked into a wallet I've used to pay for a seedbox in 2012 :)

At least you paid your bills.