In early 2020, I had an aging 2011 Air that was still struggling after a battery replacement. Even though I "knew" the Apple Silicon chips would be better, I figured a 2020 Intel Air would last me a long time anyway, since my computing needs from that device are light, and who knows how many years the Apple Silicon transition will take take anyway?

Bought a reasonably well-specced Intel Air for $1700ish. The M1s came out a few months later. I briefly thought about the implication of taking a hit on my "investment", figured I might as well cry once rather than suffer endlessly. Sold my $1700 Intel Air for $1200ish on craigslist (if I recall correctly), picked up an M1 Air for about that same $1200 pricepoint, and I'm typing this on that machine now.

That money was lost as soon as I made the wrong decision, I'm glad I just recognized the loss up front rather than stewing about it.