Spend time with a man in his 50s or 60s who’s done the deep inner work, and you’ll notice something right away:
He’s not giving advice to impress you.
He’s offering what he wishes someone had told him—before it was too late.
We asked a group of older men:
“What’s one choice you’d make differently if you had the chance to go back?”
Their answers were raw. Honest. And rich with the kind of life wisdom no therapist, coach, or self-help book can fake.
Here’s what they shared. Consider these invitations—not from perfect men, but from ones who’ve grown through pain.
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1. Own Your Mistakes Sooner
“I could’ve spared myself and others so much heartache if I had just said, ‘That was my fault. I’m sorry.’”
Defensiveness builds walls. Accountability builds trust. Growth begins the moment you stop blaming and start owning.
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2. Stop Performing. Start Being
“I spent years becoming the version of myself I thought people wanted. I lost track of who I really was.”
Authenticity isn’t just trendy—it’s vital to mental peace. Let go of the mask. Start living from your core.
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3. Approval Is Addictive—and It Costs You
“I chased achievements I didn’t even want, just to feel accepted.”
Trying to earn love through performance is exhausting. Real peace comes when your actions align with your values, not someone else’s expectations.
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4. People Don’t Need You to Fix Them. They Need You to See Them
“I offered advice when all they needed was presence.”
Connection begins when we stop trying to solve and start simply listening. Empathy > answers.
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5. Do the Inner Work Before You Try to Build a Relationship
“My unresolved wounds leaked into every relationship I had.”
We all carry stories. But until you tend to yours, you’ll keep acting them out—with the people you love most.
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6. Don’t Follow the Timeline. Follow Your Readiness
“I got married because I thought I should. I wasn’t ready, and it hurt both of us.”
Milestones mean nothing without emotional maturity. Give yourself permission to move at your own pace.
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7. Friendship Needs Maintenance—Or It Fades
“I let my friendships die off. Now I miss the connection I once took for granted.”
Men need close friendships too. Reach out. Be honest. Don’t wait until you’re in crisis.
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8. Pain That’s Ignored Becomes Pain That’s Inflicted
“I didn’t realize how much my hurt was hurting other people.”
You’re not responsible for what wounded you. But healing? That’s yours to own. Don’t delay it.
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9. Start Thinking About Your Future Self Now
“I spent so much trying to feel important. Now I’m trying to catch up.”
Wealth isn’t status—it’s stability. Make decisions today your older self will thank you for.
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10. Express Gratitude While You Still Can
“I assumed people knew how much they meant to me. I was wrong.”
Don’t wait. Say the words. Gratitude is powerful medicine for relationships.
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11. Don’t Abandon Yourself for Someone Else
“I changed who I was to please someone. In the end, I lost both of us.”
Compromise is part of love. Self-erasure is not. Stay rooted in who you are.
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12. Ending a Relationship Honestly Is Better Than Betrayal
“I cheated because I didn’t know how to leave. I carry that regret every day.”
Have the hard conversation. Do the brave thing. Integrity matters more than comfort.
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13. “Just This Once” Often Becomes a Pattern
“The little shortcuts cost me more than I ever imagined.”
Quick fixes usually come with long-term consequences. Choose with intention, not impulse.
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14. Speak the Hard Truths. Even If It’s Scary
“I bottled things up for decades. Eventually, it broke me.”
Your voice matters. Vulnerability is strength, not weakness. Practice it now.
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15. Your Loyalty Shouldn’t Cost Your Wellbeing
“I stayed at jobs that drained me because I didn’t know I could leave.”
Burnout isn’t a badge of honor. Prioritize yourself—not just your paycheck.
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16. Don’t Go Into Debt to Win Approval
“I became a lawyer for my father. I hated it. And I’m still paying for it—financially and emotionally.”
Honor your path. Not your parents’ dreams. You deserve a life that feels right, not just looks right.
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17. Choose the Person in Front of You—Not the Fantasy
“I overlooked red flags because I wanted the story to work.”
You’re choosing a partner, not a project. Pay attention to how you feel, not just how it looks.
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18. Care for Your Body Like It’s a Privilege—Because It Is
“I didn’t stretch. Didn’t rest. Didn’t listen. Now I’m paying for it.”
Your body is your home. Treat it with care—because it keeps the rest of your life possible.
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19. Keep Learning. It Keeps You Young And Ensures Your Success
“Books gave me the insight I wish I’d had 30 years ago.”
Growth doesn’t stop when school ends. Emotional wisdom is earned—one page, one insight, one reflection at a time.
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20. Enter Their World. It’s Where Connection Lives
“I always said ‘no’ to her hobbies. Now I wish I had those memories.”
You don’t have to love it. You just have to show up. Shared experiences are a foundational pillar of a happy romantic life.
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21. College Is About More Than a GPA
“I missed out on living because I thought the grades were everything.”
Connection, exploration, and discovery are just as important as performance. Make space for life.
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22. Numbing Only Delays Healing
“What started as a way to relax became something I couldn’t stop.”
Unfelt feelings don’t disappear—they just get buried. Face what hurts. The only way out is through.
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23. You Are Not Your Job
“I gave everything to work. When I stopped, I didn’t know who I was.”
You’re more than your title. Protect your peace. Reclaim your identity beyond productivity.
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24. You Deserve Joy—Now
“I thought I had to earn happiness. I didn’t.”
Joy isn’t a reward—it’s a practice. Allow yourself to feel it now, not after you’ve done ‘enough.’
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Final Thought:
These aren’t just mistakes.
They’re guideposts.
From men who’ve done the work—
and want to save you the detours.
You don’t have to wait until life humbles you to begin living more intentionally.
Start now.
With compassion.
With courage.
With mindfulness.
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PODCAST LINKS FOR TRAILER:
Wanna Climb Higher Up The Happiness Hill ? Here’s Where To Begin Your Ascent:
For info on Dr. John’s Ultimate Online Anger Management Course (which has over 20,000 graduates!), visit his High Performer Shop at https://guide-to-self.mykajabi.com/store.
Top tools for emotional mastery and high tech execs from the best executive coach in Silicon Valley:
The best podcast for relationships and those who want to create a happier, safer love life:
For the tremendous work Dr. John & Joree are doing to heal relationships, visit their top couples counseling site: LoveIsntEnough.net
️ Straight talk on evolution, masculinity & growth on the best podcast for men:
Joree’s expert work on mindfulness, therapy & transformation from the best therapist for women near you:
For more info on the superb counseling Joree is doing with women who are stuck in their lives, visit her site at MindfulnessAndTherapyCenter.com
The best podcast for women who seek to get unstuck in live and make the next 30 years better than the last 30: