Based on research from Cornell, Northwestern, Concordia University, and the Journal of Adult Development

Core Principles (apply at every age)

[ ] Default to action over inaction. Inaction regrets outnumber action regrets ~2:1 by your 30s and beyond. When in doubt, lean toward trying.

[ ] Choose growth over obligation when they conflict. “Ideal-self” regrets (not becoming who you hoped to be) outweigh “ought-self” regrets (not meeting obligations) by roughly 3:1.

[ ] Reach out first. Staying in touch with friends and family is one of the most consistent, low-cost regret-preventers across every study.

[ ] Process regret once — don’t ruminate. Rumination correlates with worse well-being. Extract the lesson, then let it go.

In Your 20s
[ ] Take the relationship risk, the move, the unconventional path — regrets here center on relationships and leisure, and the “opportunity window” feels widest now.

[ ] Start building health habits (exercise, sleep, checkups) — costs little now, prevents the most irreversible regret category later.

[ ] Don’t wait for “the right time” to pursue what you actually want — this is when ideal-self regrets get seeded.

In Your 30s

[ ] Prioritize family closeness deliberately — work/family regrets start overtaking relationship/leisure regrets right around here.

[ ] Ask for the raise / negotiate — a majority of people report regretting not doing this.

[ ] Notice if you’re staying somewhere (job, city, relationship) out of inertia rather than choice.

In Your 40s–50s

[ ] Reassess career fit honestly — this is peak career-regret territory; most of it centers on missed opportunities, not bad choices made.

[ ] Don’t let work consume family time — one of the most common reported regrets, especially among men.

[ ] Address health issues now, before they become irreversible.

In Your 60s+

[ ] Focus on repair, not relitigation — reconnect with estranged people, resolve what’s fixable.

[ ] Let go of what can’t be changed — the 60+ group reports the highest happiness of any age group, largely by doing this well.

[ ] Give yourself permission to be happy — “I wish I’d let myself be happier” is one of the most common deathbed regrets, and it’s about permission, not circumstance.

Quick Gut-Check Question
“Will I regret the swing and miss, or the swing I never took?”

Across nearly every study, the never-taken swing haunts people longer.