Old Dudes. Big Regrets. Savage Wisdom Every Young Man Needs to Hear.
I’m a big fan of asking our elders the good stuff. Not just “what was gas priced at?” kind of stuff. I mean real, soul-level, holy-crap-why-didn’t-someone-tell-me-this kind of stuff. Partly, this fascinates me because I want to learn from others – particularly those who’ve been there before so I can avoid their biggest life mistakes. No need for us to make the same mistakes simply by listening. I was once told an idea which I love: “Be like the ninja; steal with the eyes and ears.”
So I asked my male clients over 50 one painfully honest question:
👉 “What’s one mistake you made in life that you wish Past You hadn’t completely screwed up?”
And man, they delivered.
Here’s what they said—raw, real, occasionally brutal, and exactly what every young man should hear before he tanks a relationship, a career, or his spine.
1. Own Your Sh*t and Say ‘Sorry’ Faster
“I could’ve skipped 80% of arguments if I just said, ‘Yep, that was on me.’ I am truly sorry.”
Don’t be that guy who dies on a hill of ego. Learn to apologize like a grown-ass man. Shame makes it hard. Maturity makes it easier. Accountability = power. Not weakness. Work on your shame so that you can quickly own your mistakes. That’s true power, not weakness. Accounatability stengthens your relationships by forging greater trust and safety.
2. Stop Performing. Start Being
“I wasted YEARS trying to impress people who didn’t matter.”
Being “cool” is the biggest scam going. Authenticity is the real flex. Be the kind of guy who’s comfy in his own skin—not the one molding himself into a human LinkedIn profile. Pretending to be someone else to win approval makes you look insecure. Authenticity attracts the right people. Being comfortable in your own skin? That’s real swagger.
3. F*ck External Validation
“I wish I’d lived the life I wanted, not the one other people expected.”
One of the hallmarks of a mature, happy person is they’ve stopped living solely for the approval of others. Make the mature jump from external validation (i.e., kudos from others, likes on FB, etc.) to internal validation (i.e., complimenting yourself when you act in accordance with your top values). This is a huge step towards living a life of unflappable integrity. Likes, claps, and “atta-boys” are cheap dopamine. Get high off your own damn integrity. Compliment yourself when you do hard things. That’s the stuff that builds unshakeable self-worth.
4. Stop Fixing. Start Listening
“People don’t want solutions. They want to feel heard.”
If you’re constantly in fix-it mode, congrats—you’re low-key telling everyone they’re incompetent. Chill. Validate. Shut up and nod. Only give advice when asked. Lead with empathy and validation, not solutions. When we try to fix things for others, even if it’s due to love, we send the message that they can’t deal with it themselves. It’s disempowering. If overdoing is a big part of your persona applies, check out Teri Cole’s new book on High Functioning Codependents, Too Much: A Guide to Breaking the Cycle of High-Functioning Codependency.
5. Don’t Show Up Half-Built
“You can’t be a good partner or parent if you haven’t built your own foundation.”
Know thyself. Learn your needs. Speak them. Manage your brain. Work on being a solid human before dragging someone else into your chaos. You need a strong foundation before you support others. Work on self-awareness. Learn to manage your mind and heart. Figure out who you are, what you feel and what makes you happy. Get more comfortable in uncomfortable conversations. Learn what your needs are and practice speaking up for them.
6. Marriage and Kids Are Not Simply Life’s Next Checkbox
“I got married because it was ‘time.’ Huge mistake.”
Marriage isn’t a Costco run. Don’t do it just because it’s next. Do it because you’re ready—and the person beside you is the real deal. Don’t treat life like a checklist. These are the biggest decisions you’ll ever make—be ready. Don’t just do ‘what’s next’ because you think you should. Do them because it’s the right time for you. Think deeply. Forge your own path. Don’t just follow the crowd.
7. Keep Your Male Friends
“Most men end up isolated as hell. Don’t be that guy.”
Make the damn call. Send the text. Go to lunch. Real friendship takes effort, especially after 30. Talk feelings AND fantasy football. Masculinity doesn’t mean isolation. Find your tribe. Find the courage to be real with them. Don’t just talk about the stock market and sports. Have the stones to go deeper.
8. Don’t Be a Jackass
“I didn’t realize how much I hurt people until it was too late.”
Being traumatized isn’t a license to be an asshole. Do your healing. Build a personal code. Lead with kindness, not wounds. Live with kindness, trust and respect for others.
9. Start Investing Sooner, Dumbass
“Skip the sports car. Compound interest is your best friend.”
Seriously. Put away $300 per month starting at 18 and Future You will be loaded. Or at least not crying into a microwave burrito at 65.
10. Say ‘Thank You’ Like It’s Free (Because It Is)
“I was so focused on success, I forgot to appreciate the people who helped me get there.”
Gratitude is gold. Use it often. Credit others. Thank everyone. Gratitude builds bridges. Don’t take people for granted. Credit is free. Give it away. Practice gratitude and appreciation for small things – often. It’s classy and keeps you human.
11. Don’t Restructure Your Whole Life for a Relationship at 22
“Sometimes it works. Sometimes you end up in the Marines.”
Slow your roll. Give your brain time to finish cooking (approximately age 26!). You’ve got time.
12. Don’t Cheat On Your Partner
“If you’re done, be done. Don’t be a coward.”
Cheating is spiritual junk food: fast, easy, and makes you feel like crap after. Say what needs to be said. Don’t sneak. Don’t lie. Cheating is cowardly. Have the courage to be honest. And save yourself the anxiety and guilt of carrying around a massive secret. Do better. Be Better. If you’re considering cheating, you’re at the point of calling it done in your relatioship (or at minimum, ready to work on your ‘ship in couples counseling!).
13. Everything Has a Cost
“Your 20s football injuries will haunt your 60s.”
Enjoy the now. But don’t screw over your future self just to bench press 275 today. Especially if no one’s watching.
14. Say What You Feel. Out Loud.
“I wish I’d had the balls to express my feelings.”
Most men suck at this. Fix that. Learn to feel. Learn to speak up. Don’t wait until you’re 70 to tell people you love them. This one is all about authenticity, honesty and speaking your truth. The problem is most of us think we are self-aware and know how we feel. Unfortunately, only 12-15% of us actually ARE self-aware of our thoughts, feelings and our impact on others. Work to increase self-awareness. Start with a mindfulness practice to help you tune in to your internal world to become more familiar with your thoughts and emotions. Once you become more aware, have the courage to share how you truyl feel with your loved ones.
15. Know Your Worth at Work
“Hard work doesn’t mean being a doormat.”
You don’t get what you don’t ask for. Advocate for yourself. Say no. Learn to rest without guilt. Hustle culture is not a personality. Burnout is real. Say no. Learn how to “be” instead of “do.”
16. Don’t Pick a Degree That Leaves You $500k in the Hole and Hating Life
“I know a dentist half a million in debt and hates his job. Don’t be that guy.”
Look at cost vs. payoff. Your degree is a tool, not an identity. Choose wisely. Be strategic. Don’t enter adult life in a financial hole without a plan. Don’t be a “dentist.”
17. Who You Marry = The Biggest Decision of Your Life
“Choose character. Choose mental health. Choose family dynamics.”
You’re not just marrying them. You’re marrying their coping mechanisms, family trauma, and financial habits. Choose with eyes wide open. Make sure your values match—especially around money. Ensure they are honest and live with integrity. Make sure that they (and their family members) are mentally healthy. Your children will not likely be the genetic exception.
I learned this lesson the hard way. I did not factor in genetics, mental health or integrity as highly as I should have. Years later, my life got blown up as a result. I got married too young. I had too little relational experience. They say you never really know someone until you divorce them. In the end, I was “introduced” to the dark side of my ex-wife with a highly contentious, expensive divorce filled with lies and public personal attacks. Learn from my mistake. Know who you are marrying. It’s the single most important decision of your life.
18. Respect Your Spine
“You won’t miss it… until it’s gone.”
Stretch. Lift smart. Fix your damn posture. Your back is like trust—once it’s gone, it’s hard to get back.
19. Fall in Love with Books (or Audiobooks, Lazybones)
“Books saved me—too late.”
Knowledge is power. Read. Listen. Learn. If you’re not feeding your brain, it’s just marinating in memes and Red Bull. So many young men have told me “I hate reading!” Stop making excuses. Work at it. If you can’t read due to a disability (e.g., ADHD, dyslexia, visual processing disorder), listen to audiobooks. Watch educational talks on YouTube. Books are soul food. They change your perspective, open your mind, and nourish your character. Learning is one of the best ways to conquer life.
20. Say Yes to Her Interests
“I didn’t realize how much connection I missed by saying ‘no.’”
Dance class? Pottery? Vegan sushi night? Just go. Netflix and silence. Push out of your comfort zone. Connection happens in effort, not just words. One foundational pillar of a happy, healthy relationship is shared experiences. Discover the ones you didn’t even know existed.
21. College Is More Than a GPA
“I stayed in my dorm. I missed life.”
Say yes to invites. Make friends. Learn people. Life is relationships. The ones you build now may save your ass later. If you’re struggling to step outside your dorm room, look at your beliefs about people in general (e.g., To what extent do you think people are trustwothy in general? Kind? Helpful? Stupid? Hurtful?). Challenge your deeply held beliefs that don’t serve you. Say ‘yes’ to invites. Practice being social. Push past your discomfort. Screw your social anxiety. You will reap the rewards because positive relationships are a foundational pillar of a happier life.
22. Don’t Use Booze or Nicotine to Cope
“Started as fun. Ended in chains.”
Nothing wrong with safely partying (i.e., have a safe way to get home, Maynard!). But if you need it to feel OK, it’s not fun—it’s a leash. Watch yourself.
23. Work Less. Live More.
“I wish I hadn’t worked so damn much.”
Time and attention = love. Don’t give your best energy to a job that won’t even come to your funeral. Upon their deathbed, nobody wishes they’d spent more time at work. We regret the missed opportunites to hang out with loved ones, family and friends. Too many times, I’ve worked with men who’ve given the vast majority of their time and attention to their job. Unfortunately, time and attention are also the currency of relationship. If you’re giving too much to work, you’re denying it to your loved ones. Resentment inevitably accrues as a result, leading to an unhappy home life.
24. Let Yourself Be F*cking Happy
“I wish I had let myself enjoy life more.”
Happiness is largely about learning to enjoy the journey of life. Not so much about the destination. Partly, this is due to the fact that we don’t reach large celebratory destinations very often (e.g., high school graduation, getting a new job, getting married, promotions are too infrequent). We need daily causes for positive emotions (e.g., awe, wonder, curiousity, relaxation, anticipation, passion, excitement, appreciation, gratitude and more). Happiness comes in very small packages if we know where to look. One study found we get a positive emotional boost from something as small as finding a quarter on the ground or a gift of three Hershey kisses. Find your small things throughout the day and reap the emotional rewards. Joy doesn’t live in achievements. It’s in the small stuff—sun on your face, a great cup of coffee, laughing until your ribs hurt. Notice that sh*t. Learn to be an expert spotter of your positive emotions. Purposefully create those situations. Every day.
Final Thought:
These aren’t just regrets — they’re invitations.
To live smarter.
To love deeper.
To push out of the comfort zone and embrace more of life.
To live without regret.
To build a life you won’t need to escape from.
These are cheat codes. Breadcrumbs from the other side of the mountain.
Use them. Live smarter. Love harder. Be authentic. Discover what gives you small bursts of joy and pride and relaxation and awe.
And build a life you won’t need to numb, escape from, or apologize for later.
Let’s evolve. Together.
Wanna Climb Higher Up The Happiness Mountain? Here’s Where To Start Your Ascent:
👔 For Dr. John’s work helping execs and high performers stop silently imploding and learn to smile & laugh more:
😡 For info on Dr. John’s Ultimate Anger Management Course (which has over 20,000 graduates!), visit his High Performer Shop at https://guide-to-self.mykajabi.com/store.
💔 Curious about the couples counseling magic John’s doing with the amazing Joree Rose, LMFT
(Spoiler: Love isn’t enough, but skills, self-awareness, and maybe a glass of wine are.)
🎙️ For all things caveman evolution, podcast-style:
💃 For Joree’s powerhouse work helping women ditch burnout, find joy, and stop dating emotionally unavailable man-children:
📸 For more info on the superb counseling Joree is doing with women who are stuck in their lives, visit her site at MindfulnessAndTherapyCenter.com
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