If you’ve ever talked to a man in his 50s or 60s who’s done some real soul work, you know this:
He’s not trying to impress you. He’s trying to spare you. His past pain.
I asked a group of men over 50, “What’s one mistake you’d avoid if you could go back in time for a ‘do-over’?”
The responses? Candid. Cutting. And full of the kind of wisdom you don’t get from Instagram quotes or locker room advice.
Here’s what they said—lessons paid for in pain and tears, and offered to you for free.
—
1. Take Responsibility Before You Get Defensive
“I could’ve saved so much time and heartache if I’d just said, ‘You’re right. That was on me. I’m really sorry.’”
Being accountable doesn’t make you small. It makes you a man. It makes you accountable. And ultimately, it makes you trustworthy. The longer you delay ownership, the longer you stay stuck.
—
2. Stop Trying to Be Liked. Start Trying to Be Real.
“I spent years acting like who I thought people wanted me to be. I barely knew myself.”
Authenticity isn’t a buzzword—it’s the foundation of peace. Drop the act. You’re not for everyone, and that’s the point.
—
3. If You Live for Approval, You’ll Die by Rejection
“I followed the script: school, job, marriage, house. None of it felt like mine.”
Living someone else’s version of success will bankrupt your soul. Get clear on your values—and let them guide the way.
—
4. Don’t Solve People. See Them.
“I kept jumping in with advice when all they needed was for me to listen.”
People aren’t puzzles to fix. Learn to hold space without taking over and offering your platitudes and fixes. That’s when trust deepens.
—
5. Heal First. Then Love.
“I brought my unhealed wounds into every relationship. And it showed.”
You can’t build connection on a cracked foundation. Do the inner work. Make peace with your past. Your future relationships depend on it.
—
6. Milestones Mean Nothing Without Readiness
“I got married because I thought I was supposed to. I wasn’t.”
Life isn’t a checklist. Wait until the ‘why’ is yours—not just because it’s ‘time.’
—
7. Keep Your Friendships Alive—or You’ll Wake Up Lonely
“I let my friendships fade. Now I don’t know who to call.”
Male friendship takes effort. Make the call. Plan the hang. Say what’s real. Brotherhood doesn’t happen by accident.
—
8. Unhealed Pain Becomes a Weapon
“I didn’t know how much damage I was doing until it was too late.”
Your trauma isn’t your fault—but what you do with it is. Face it now, or bleed on people who didn’t cause it.
—
9. Your Future Self Is Watching. Save Money.
“I blew cash trying to feel successful. Now I’m playing catch-up.”
Start small. Stay steady. Wealth isn’t flashy—it’s freedom.
—
10. Gratitude Isn’t Optional
“I never told people how much they meant to me. I thought they knew.”
Don’t assume. Say it. Gratitude softens life. It costs nothing—and changes everything.
—
11. Don’t Sacrifice Your Path for Someone Else’s
“I changed careers for a girl. That story didn’t end well.”
Love someone fully, but don’t erase yourself to do it. A good relationship doesn’t require self-abandonment.
—
12. Cheating Isn’t an Escape. It’s a Cop-Out.
“I cheated because I didn’t have the guts to end it. I still regret it.”
If something’s over, be honest. Walk out with your integrity intact. Avoidance just creates more pain.
—
13. Every Shortcut Has a Long-Term Cost
“Back injuries, bad habits, broken trust—they all started with ‘just this once.’”
Short-term wins can carry long-term losses. Think in decades, not weekends.
—
14. Say the Thing. Even If Your Voice Shakes.
“I kept my feelings bottled up for years. It wore me down.”
Emotional honesty is a muscle. Use it or lose it. Silence might feel safe—but it’s expensive.
—
15. Know When to Walk—Especially at Work
“I stayed loyal to companies that weren’t loyal to me.”
Advocate for yourself. Don’t confuse overworking with value. Burnout isn’t a badge of honor.
—
16. Don’t Go Into Massive Debt Just to Please Your Parents
“I became a lawyer to make my dad proud. I hated every second of it.” I know an M.D. who is $500k in debt and hates his job. Don’t be that guy.
Degrees, careers, titles—none of it matters if it’s killing your spirit. Build a life that feels good, not just one that looks good.
—
17. Marry the Person, Not the Fantasy
“I ignored red flags because I wanted the story to work.”
You’re not just choosing a partner—you’re choosing your emotional climate. Choose character over charisma.
—
18. Treat Your Body Like It’s the Only One You’ll Get
“I didn’t think twice about my back until I couldn’t tie my shoes without pain.”
Stretch. Strength train. Rest. Protect your physical freedom—it’s what lets you keep showing up.
—
19. Read. Constantly.
“Books gave me insight I wish I had decades earlier.”
Make time to learn. About people. About relationships. About yourself. Emotional intelligence is built—not inherited. One of the most powerful values you can adopt is lifelong learning. Start now.
—
20. Say Yes to Her World Sometimes
“I always said no to her hobbies. Now I wish I had those memories.”
Join her. Even if it’s not your thing. Shared experience builds depth. The activity matters less than your presence.
—
21. College Isn’t the Whole Story
“I focused so much on GPA, I forgot to actually live.”
Grades fade. Relationships, experiences, self-discovery—those last. Say yes to more than just assignments. Meet people. Step out of your comfort zone and be social.
—
22. Don’t Numb Your Feelings. Learn to Face Them.
“What started as a drink to unwind became something I couldn’t stop.”
Avoiding pain creates more of it. Learn to sit with discomfort. It passes. Numbing just delays the work.
—
23. Clock Out More Often
“I gave everything to my job. It didn’t give back.”
Your work isn’t your worth. Protect your time like it matters—because it does.
—
24. Let Joy In. No Permission Needed.
“I didn’t know I was allowed to enjoy life. I thought I had to earn it.”
Happiness isn’t a finish line. It’s a practice. Let it happen now—not later.
—
One Last Thing:
These aren’t just regrets.
They’re invitations.
To live on purpose.
To love with intention.
To become the kind of man you respect.
Not perfect. Just present.
Start today. You don’t need to be older to be wiser.
—
Wanna Climb Higher Up The Happiness Hill ? Here’s Where To Begin Your Ascent:
😡 For info on Dr. John’s Ultimate Online Anger Management Class (which has over 20,000 graduates!), visit his High Performer Shop.
🧠 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:
🎙️ 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:
Recent Comments