How do I live with myself knowing I’ve failed to ‘cash out’ multiple times?

I’m going to be brutally honest and not sugarcoat this; I have been an idiot and am now doing some soul searching. Also, if it isn’t clear, when I say “how do I live with myself” I am not implying I don’t want to live, I’m fine. Very annoyed with myself, much less wealthy than I should be, but otherwise fine.

So, story time (TL;DR: at the bottom)

I’ve been ‘in crypto’ since about 2018 and have now experienced two major cycles in which, at their peak, I had life changing money. Not “in theory” but literally right there and ready to sell, yet I didn’t both times…

I won’t give specific numbers since what I define as life changing for me may be different to you, but it very likely would have set me up rather well at my age, though perhaps not for life. We are talking buy a nice house and not care about working for a few years money.

The first time was in 2021, I had accumulated (over a couple of years) a healthy bag of a crypto called QNT, you might have heard of it. I was buying that sucker way before it was on people’s radar for cheap, in fact I was mocked in certain communities for being so bullish. Needless to say I was somehow right, and it really took off. I had ‘made it’. I saw all that potential sitting there, and what did I do? I flaked out, started worrying about taxes and missing out on more gains, and ended up rotating back into other projects which didn’t do as well (for a time.)

Fast forward to 2024 and somehow, against all odds, I was back. I had almost got to my previous high point via investing in other projects and, perhaps stupidly, rotating some of those gains back into even riskier projects. Amazingly, those moves paid off too. I couldn’t lose. At this point I am now even better off than I was back in 2021. And what did I do? NOTHING. I just sat on it, watched it slowly dissolve, and did nothing.

Now in the present day, I’ve had to sell small amounts to make ends meet, and move some stuff around, but most of the assets that were big in 2024, which I still hold, are utterly dead now. I can’t really see them making a comeback. I had beaten the casino twice, and never cashed out. Now I feel like lightning will not strike 3 times and I’m gonna be ‘that guy’ forever haha. I’m back to square one.

Honestly, how would you even approach this? What can I tell myself? I have no choice but to hold on at this point and hope something turns around from the ashes I’m holding onto, but I’m starting to think I missed the only opportunities I’ll ever have to make that sort of money due to self doubt, and to a much lesser extent, greed.

TL;DR: I ‘made it big’ back to back, and failed to enjoy any of the spoils.