Wise Elders Share Their Biggest Regrets — Every One Should Hear These (To Avoid Them Later In Life)
I’m a huge fan of tapping into our elders for wisdom. I want to be able to look back on my life upon my deathbed with no regrets. So I asked my male clients over 50 this simple yet profound question:
“What’s one mistake you’ve made in life that you wish the past you could have avoided?”
Here’s what they said — raw, real, and packed with hard-earned wisdom.
1. Own Your Sh*t And Apologize More Quickly
“I could’ve avoided a ton of pointless arguments if I had just said, ‘You’re right, that was on me. I’m sorry.’”
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. Don’t Be ‘Cool’—Be Real
“Trying to impress people who didn’t matter wasted years of my life.”
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. Live For Internal Validation, Not External Validation
“I wish I’d had the courage to live a life true to myself, not the life others expected of me.” This is one I speak with clients about often. One of the hallmarks of a mature, happy person is they’ve made the shift from 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.
4. Stop Trying to Fix Everything
“Most people just want to feel heard. Unless someone asks for advice, just listen.”
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. Build Yourself First
“Don’t bring a half-formed version of yourself into a relationship or parenthood.”
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 Aren’t ‘Next Steps’
“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. Maintain Male Friendships
“We lose our male friends over time – people move, disagreements, lack of contact, getting busy with your own life. So we need to learn to reach out- phone call, text, lunch, drinks. You’re gonna need them—emotionally and mentally.”
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. Be a Decent Human
“I didn’t realize how much pain I caused others until it was too late.”
Trauma isn’t an excuse to treat others poorly. Create your own moral code. Live by it. Live with kindness, trust and respect for others.
9. Start Investing Early
“Skip the cars and clubs—compound interest is magic.”
Start at 18. Simply saving $300 per month can change your future. your future self will thank you.
10. Recognize the People Who Help You
“I was so hyper-focused on achieving that I forgot to say ‘thank you.’”
Gratitude builds bridges. Don’t take people for granted. Credit is free. Give it away. Practice gratitude and appreciation for small things – often.
11. Don’t Make Major Life Decisions for a Relationship Before 25
“Sometimes it works out. Sometimes you end up in the Marines.” Take your time. You have plenty of it. Give yourself time for your brain to fully mature (about the age of 26!).
12. Don’t Cheat
“If you’re done, be done. Don’t sneak around. Don’t have an affair. It lacks integrity and isn’t worth the guilt.”
Cheating is cowardly. Have the courage to be honest. And save yourself the anxiety and guilt of carrying around a massive secret.
13. Everything Has a Price Tag
“Playing football in your teens? MMA in your 20s? Pushing your body to the max? You’ll feel it in your 60s. Be kind to your future self.”
Know what you’re trading long-term for short-term highs.
14. Don’t Burn Bridges
“Leave relationships with grace and kindness. Don’t shit talk others. You never know whose help you’ll need down the road.”
Bitterness only hurts you. Be the bigger person when things end. Practice daily forgiveness to let go of that old stale anger.
15. Know Your Worth at Work
“Hard work doesn’t mean letting yourself be taken advantage of. Know how much you’re worth and ask for it. You don’t get what you don’t ask for.”
Burnout is real. Say no. Learn how to “be” instead of “do.”
16. Vet Your College Degree
“Know what it costs. Know what it earns. Look for value over prestige.”
Be strategic. Don’t enter adult life in a financial hole without a plan. I know a dentist that is $500k in debt and hates his job. That’s a lifetime of a problem. Don’t be that dentist.
17. Who You Marry = Your Biggest Financial Decision
“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. Take Care of Your Back
“You won’t miss it… until it’s gone.”
Lift smart. Stretch. Invest in your posture, flexibility and strength.
19. Read More
“The biggest regret of my life is not falling in love with books sooner.”
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. Be Open to Her Interests
“If she invites you to do something new, try it. Even if it turns you off intiially. 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 yours.
21. Don’t Waste College Locked in Your Dorm
“I missed the chance to build lifelong friendships. I passed up a ton of social experiences. Don’t make the same mistake.”
Step out. Look at your beliefs about people in general (e.g., To what extent do you think people are trustwothy in general? Kind? Helpful? Hurtful?). Challenge beliefs that don’t serve you. Say yes to invites. Practice being social. Push past your discomfort. You will reap the rewards as positive relationships are a foundational pillar of a happier life.
22. Avoid Nicotine & Alcohol As Coping Tools
“It starts as fun and quickly becomes a prison.”
Addiction is easy. Recovery is hard. Protect your future self.
23. Balance Work With Family, Friends, Hobbies
One of the biggest regrets of older folks is “I wish I hadn’t worked so hard.” Upon your 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 the currency of relationship. If you’re giving too much to work, you’re denying it to your loved ones. Resentment inevitably accures as a result, leading to an unhappy home life.
24. Know And Share How You Feel
Another classic regret of those in the final quarter of life is “I wish I’d had the courage to express my true feelings.”
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 impact on others. Work to increase self-awareness. Start with a mindfulness practice to help you tune in to your internal world to beomce more familiarized with your thoughts and emotions. Once you become more aware, have the courage to share how you truyl feel with your loved ones.
25. Give Yourself Permission To Enjoy The Journey
Another hall of fame regret is “I wish I had let myself be happier.”
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 happen all too infrequently). 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.
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.
Let these stories from the other side of the hill be the flashlight guiding your path. Let’s evolve. Together.
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