20 Things Boomers Wish They Told Their Younger Selves
Wisdom hits differently when it’s earned the hard way, just like these 20 things the older generation wishes they could tell their younger selves.
- Chris Graciano
- 4 min read
Hindsight is 20/20, and for many Baby Boomers, experience has delivered some powerful life lessons. From financial tips to relationship regrets, there’s a lot they wish they’d known sooner. Here are 20 pieces of advice they’d shout back to their younger selves if they could.
1. Start Saving Earlier
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Compound interest is magic—if you give it time. Most Boomers admit they didn’t realize how quickly the years (and expenses) add up.
2. Don’t Sweat What Others Think
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The opinions that felt huge in your 20s? You won’t even remember most of those people later. Live how you want—chances are, they’re too busy worrying about themselves anyway.
3. Travel While You’re Young
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Knees don’t last forever. Boomers often wish they’d explored more before responsibilities piled on. Youth and freedom are a golden combo—don’t waste them waiting.
4. Stop Trying to Be Perfect
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Perfection is a trap that steals joy. Being “good enough” is actually great. Most of the people trying to look perfect are struggling behind the scenes anyway.
5. Take More Risks
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The regrets aren’t usually about what they tried—it’s what they didn’t. That job, move, or leap of faith? Do it. Playing it safe doesn’t always pay off.
6. Stay Close to Real Friends
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Be friends not with the flashy ones but with the loyal ones. Boomers say nurturing a few deep friendships beats collecting hundreds of surface-level ones.
7. Health Isn’t Forever
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Eat better, move more, and get checkups. You won’t realize how precious your health is until you start losing it.
8. Learn to Say No Sooner
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Too many said yes to things they didn’t want to do—jobs, relationships, favors. Saying no doesn’t make you selfish. It makes you honest.
9. Document the Small Moments
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Everyone snaps pics at weddings and vacations, but Boomers say the little everyday memories hit harder. Sunday breakfasts, goofy faces, your parents laughing—don’t miss those.
10. Invest in Experiences, Not Stuff
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That fancy car? It won’t age well. However, that weekend camping trip with friends is the memory that lasts.
11. Forgive Faster
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Holding on to grudges is like drinking poison and expecting someone else to hurt. Most things don’t matter as much as we think.
12. Stop Comparing Yourself
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There will always be someone richer, prettier, more successful, but there’s only one you. Run your own race.
13. Listen More Than You Talk
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Everyone wants to be heard. The best relationships come from really listening—not waiting to speak.
14. Learn a Skill Outside Work
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Not for money—just for joy. Whether playing guitar, woodworking, or painting, Boomers wish they’d made more time for hobbies.
15. Marry for the Right Reasons
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Marry not because of pressure, loneliness, or a timeline. The right partner makes life richer—the wrong one makes it harder.
16. Take Care of Your Mental Health
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Back then, nobody talked about mental health. However, Boomers say they wish they’d known it was okay to ask for help.
17. Don’t Ignore Your Kids’ Childhood
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Work will wait; childhood doesn’t. Be there for the bedtime stories, the school plays, the bad jokes—they go by fast.
18. Time is the Real Currency
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You can earn more money, but you can’t earn more time. Spend it where it counts.
19. Don’t Be Afraid to Start Over
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New town, new job, new love—it’s never too late. Boomers who took big pivots say it changed everything. Comfort zones kill growth.
20. Laugh at Yourself Often
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Life’s too weird and unpredictable to take so seriously. Mess up, move on, laugh. Humor might just be the best survival tool there is.