Earlier quoted context omitted.
When hindsight points out the opportunities that you overlooked which would have giving you that comfortable life it infects all future decision making.
Is there a spoiler tag on HN ? These ones still hurt: There is a lot of thing one could have done "for the LULz" but decided to browse HN, Imgur or Reddit instead. - Bitcoin. I heard about it when it was still possible to mint it on CPU, but chose to run SETI@Home instead. - Bitcoin when it was at merely $9000. - Ethereum when it was going under $1. - Dogecoin like anytime before yesterday (up 6x or something today).…
We remember the winners we missed way more than the losers, because the winners are still present in our lives today, whereas the losers never became noteworthy (because they lost).
But it’s extremely difficult to tell them apart ahead of time. So current me needs to give past me a pass... past me failed at something that is very difficult; no shame in that. Wistful regret, maybe, in a “what if...” kind of way, but I think everyone has those in their life, and not just about money.