The Top 10 Regrets of Dying Men (And How You Can Prevent Them!)
The Top 10 Regrets Men Have Before They Die (And How to Avoid Them)
Here’s a question most men never ask themselves until it’s too late: If you found out today you had six months to live — what would you regret?
Turns out, the answer is almost entirely predictable. And preventable. Researchers have been interviewing men in hospice care, in their 70s and 80s, men who built impressive careers and full lives — and the same ten regrets show up over and over, regardless of income, culture, or zip code.
Which means two things: you’re not uniquely screwed up. And these regrets can be avoided.
In this episode, Dr. John Schinnerer breaks down the ten most common regrets men report later in life, what the research actually says about how regret works (hint: the things you didn’t do hurt worse than the things you did), and the single pattern underneath all of it that most men never see until it’s too late.
You’ll hear about the attorney who showed up to every recital and missed his daughter’s entire childhood. The project manager who retired fully funded and spent eight months in an empty fog. The guy who spent 25 years saying he’d walk the Camino de Santiago — until his knees made the decision for him.
This isn’t a shame spiral. This is a heads-up. A roadmap of the terrain most men walk blindly into — and a set of tools for navigating it differently while there’s still time.
In this episode:
- Why inaction regrets are more painful and persistent than action regrets (Northwestern research)
- The “impact bias” — why men massively underestimate how bad future regret will feel
- The top 10 regrets men report most consistently as they age
- The Inner Board Meeting model — and why most men have the wrong executive running their life
- A one-week assignment that actually moves the needle (no journaling required)
- The launch of Proximity Coaching — AI coaches built on 30 years of real psychology, available 24/7 at proximitycoaching.com
If you’ve had any version of the thought “I’ll get to that later” — this episode is for you.
Try Proximity Coaching free: proximitycoaching.com Email John: John@guidetoself.com Instagram: @theevolvedcaveman
Research cited: Roese & Summerville (2005); Gilovich & Medvec (1995); Carstensen (2006); van der Kolk (2014); Levenson, Carstensen & Gottman (1994)
Here is the link to the podcast on Apple Podcasts: The Top 10 Regrets of Men (And How To Avoid Them!)
And here is a transcript of John’s discussion on how you can avoid the biggest, baddest regrets in life. Believe me, you’ll be happy you course corrected at a young age!a
The Top 10 Regrets of Dying Men (And How You Can Avoid Them!) – Transcript
Dr. John Schinnerer, Men’s Leadership Coach
Danville, CA, San Francisco Bay Area
Top 10 Regrets of Men – The Regret-Proof Man
Dr. John Schinnerer: Hello and welcome back to the latest episode of the Evolved Caveman Podcast. And today I wanna start out with a question, and I don’t want you to answer it out loud, I just want you to sit with it for a second. And here’s the question.
If you found out right now that you had six months left to live, what would you regret not having done?
Take a minute and let that actually land. Just sit with that for a second.
Because here’s the thing, most men don’t realize the answers to that question. They’re completely predictable. Researchers have been studying regret for decades, interviewing men in hospice care in their seventies, eighties, nineties. Men who built [00:01:00] careers and families and impressive lives on the outside and the same themes for regret show up over and over almost regardless of who you are, where you came from, or how much you’ve accomplished.
Think about that. This means we’re not talking about your unique personal, one of a kind set of failures. We’re talking about a pattern, a deeply human, almost embarrassingly consistent pattern that plays out in men’s lives, across cultures, across income levels, and across zip codes.
And the really wild part, because these regrets are predictable. They’re also preventable, and that’s what today’s episode is about. I’m gonna walk you through the top 10 regrets that men report most consistently as they age. And I’m going to show you what the pattern underneath [00:02:00] all of them actually is because once you see it, you can’t unsee it.
And once you can’t unsee it, you have a choice. I’m Dr. John Schinnerer. This is the evolved caveman. Let’s get into it.
Before we get into the list, I wanna tell you something about how regret actually works because it’s a little bit counterintuitive. Most of us think regret is about things we did wrong, the mistakes we made, the choices that blew up in our faces.
And yeah, of course those sting, but research from Northwestern University consistently shows that in action regrets. The things we didn’t do. Are more emotionally persistent than action regrets. The things we did do, we tend to eventually forgive ourselves for swinging and missing. We have a much harder time forgiving ourselves for never stepping up to the plate [00:03:00] as when Gretzky famously said, you miss a hundred percent of the shots you don’t take.
We also tend to massively underestimate how much regret will cost us. There’s a concept called the impact bias. This is our tendency to overestimate how good fortune, sorry, how good future success will feel and underestimate how bad future regret will feel. We think we’ll be fine with having played it safe.
We think we’ll make peace with the unlived version of ourselves. We don’t we mostly don’t. I wanna also name something important before we dive in. These regrets are not character flaws. They’re not evidence that you’re a bad man or a bad husband or a bad father. They’re the predictable downstream consequences of the way men are socialized the man box, say it with me, the man box that we get put in before we’re [00:04:00] old enough to know what it is or even to consent to it.
Work hard, be the provider. Don’t need anyone. Keep it together. Handle it yourself. Don’t feel that programming runs deep and it produces with stunning reliability, a very specific set of regrets. Alright, let’s go through them.
Regret number one, prioritizing work over the people you love consistently.
This one tops. Almost every life review study ever conducted, and it’s the one men are most likely to nod along with and still not actually change. Here’s how it plays out. You’re 38, 42, 47 career is either taking off or finally getting traction. The kids need things. The mortgage is a fact. And so you tell yourself, and this is the exact phrase, researcher research has documented.
I’ll make it up to them later.
Yet later, is a check that almost never clears.
As Harry Chapin sang in one of my favorite songs. Cats in the Cradle. “When you coming home, dad? I don’t know when, but we’ll get together then. We’ll have a good time then” and later never comes.
Mark was a litigation attorney. He billed 70 hours a week for most of his forties.
His daughter’s childhood, he told me, happened while he was on conference calls. He didn’t know her favorite teacher’s name. He didn’t know what she was afraid of or what she loved. He showed up to things, the recitals, the soccer games, but his brain was always somewhere else. When she left for college, he said it felt less like she was leaving and more like he had never really arrived.
He cried as he told me this, he was 61. Career goals feel urgent. [00:06:00] Family time feels like it can wait. That asymmetry is one of the most costly illusions that men carry. And I wanna be clear. I’m not saying don’t work. I’m saying know what the trade is that you’re making. Make the trade consciously because when you make it unconsciously, you tend to look back.
Realize you gave away something that mattered infinitely more than you understood at the time.
Regret number two, never learning to express or understand emotion. Not expressing emotion doesn’t just affect you. It shapes every relationship around you. Your kids grow up with a father who is present but unknowable. Who models emotional constipation. Your partner learns to stop asking for closeness and intimacy because you’ve trained her to do your friends [00:07:00] keep things surface level because that’s what you’ve taught them to expect. And then one day you look around and realize you’re surrounded by people who don’t actually know you, not the real you anyway. About the version underneath the competence and the stoicism and the roles you play and the “I’m Fine” Mask.
There’s a BBC interview that I think a lot about. A, an older British man, probably late sixties sitting in a chair as most BBC interviews are talking about men in communication. And he says, totally matter of factly men talking about their feelings isn’t optional. It’s absolutely crucial. If you wanna keep the people around you from drifting away, you have to tell them how you feel without shame, without hesitation.
And then he pauses and says, you need to deal with these things. He wasn’t talking about becoming soft, he was talking [00:08:00] about becoming real, about becoming authentic, about becoming known. The male loneliness epidemic is not a mystery. It’s the logical endpoint of centuries of emotional suppression. You can’t connect deeply with people.
You won’t let see what’s behind your mask.
Regret number three, letting fear make their decisions. Fear of failure, fear of success, fear of judgment, fear of instability, fear of being disliked, fear of looking foolish. These aren’t dramatic visible fears. They’re quiet ones. They wear suits. They show up. The moment you’re about to do the thing you actually want to do, and they offer you an extremely reasonable sounding alternative.
This isn’t the right time. I should be more prepared. The market’s not there yet. I can’t risk it with the kids in school. I’m not ready yet. I don’t feel like it. [00:09:00] Research on regret is crystal clear in action. Regrets, outlast action. Regrets. Men in their sixties almost never say, I wish I hadn’t tried to start my own business.
Rather, they say, I wish I’d tried. They don’t regret the risks that didn’t work out. They regret the ones they never had the stones to take. Dave spent 22 years in a middle management job. He despised safe salary, good benefits, soul crushing, predictability. He had an idea for a business, had it for almost a decade, and every year he found a reason.
It wasn’t the right time. His kids graduated, his mortgage got paid off. He was 58 and finally free to try. He waited six months and then retired instead. Not because the idea was bad, because by then his courage muscle had fully atrophied. He’d spent so long not taking risks, that [00:10:00] risk itself had become foreign.
Fear is not the problem. Fear is information. The problem is when fear gets promoted to CEO of your life and starts running the whole operation from the executive suite.
Regret number four, losing touch with good friends. Authentic men’s friendships are strange and fragile things. They’re a lot like bigfoot spotted, rarely, easily spooked and quick to disappear.
They tend to be activity based. We bond over doing things together, not talking about things, which works fine until the activity disappears. Different job, different city. Kids divorce the slow grind of life, and suddenly the guy you used to see every week you haven’t talked to in seven years. Here’s what the research shows.
Deep lasting friendships are among the strongest predictors of health, happiness, [00:11:00] and life satisfaction in older age. Let me say that again. Deep lasting friendships are the strongest predictors of health, happiness, and life satisfaction. Stronger than income, stronger than professional achievement, and yet men let them die with a kind of passive resignation that we’d never apply to anything else.
We actually valued. Paul retired at 64 after a 35 year career in tech. He told me that on his first week of retirement, he sat down to call someone just to talk, and he realized he didn’t know who to call. His work friendships had been entirely context dependent. Without the context they evaporated. He said it was the loneliest feeling of his life more alone than he’d ever felt surrounded by a life he’d built.
So if you have a friend, you’ve been meaning to reach out to one of those. We should grab a beer [00:12:00] sometimes situations. It’s been going on for two years. Call him now. Don’t text call. I guarantee you’ll both be glad that you did.
Regret number five, not taking care of their health while they had it. Look, I’m gonna keep this one short because it’s almost too obvious and yet apparently not obvious enough because men keep not doing it. The body you have right now is the only one you get. You know that you’ve always known that, and for most of your adult life, you’ve been treating it like a rental car, running it hard, skipping maintenance, assuming it’ll hold together until you need to return it.
Hospice nurses will tell you, and they have publicly in heartbreaking detail, that one of the most common regrets they hear from men in the final weeks of their lives is that they didn’t take care of their bodies. Not in an abstract way, in a very concrete, physical way. The inability to stand [00:13:00] without help to walk to the bathroom unassisted to carry a grandchild.
The preventive habits you skip in your forties and fifties don’t just disappear. They compound. Sleep movement, stress management, regular checkups. These aren’t wellness bro recommendations. They’re investments in your future. Ability to be physically present for your own life, move your body sleep, see a doctor, exercise.
End of regret number five.
Regret.
Number six, living someone else’s definition of a good life. I hear this one all the time, and it runs deep and usually starts early. You absorb from your parents, your culture, your school, your peer group, a very specific template for what a successful respectful man looks like to them. Stable career, good income, responsible choices, the right kind of ambition pointed in the right direction.
[00:14:00] And many men spend their entire lives chasing that template, not because they consciously choose it, because it was handed to them, and they never stopped to ask whether it actually worked for them, whether it was actually fulfilling and meaningful to them. Jim was a physician 57 years old, running a successful practice objectively thriving by every external measure.
He’d wanted to be a painter, had wanted this since he was a kid, but his father was a doctor. His grandfather was a doctor, and this expectation was simply in the air. He breathed. He picked up a brush for the first time in 30 years. A few months before I talked to him, he said he felt like he’d been reintroduced to himself.
The philosopher Heider talked about Daman the anonymous, they, that shapes most of our choices. We do what they do. [00:15:00] We want what they want. We succeed on their terms, and then we arrive somewhere respectable and wonder why we feel like a stranger inside our own life. The work. Is figuring out what you actually value, what makes your heart sing, what makes you come alive, not what you are taught to value, not what looks good, not what your dad wants you to do, what actually matters to you when nobody’s watching and nobody’s grading, you regret.
Number seven, trading life for money. I wanna be precise here because this one gets misread. It’s not that men regret making money, it’s that they regret what they gave up to make it and didn’t realize they were making that trade until it was already too late. Surveys of Gen X Americans in their financial planning [00:16:00] years find the same thing.
Financial regret is almost never about money itself. It’s about the safe life decisions that got made and the dreams that were buried in order to make more money. The job that paid better but required 80 hours a week. The relocation that made financial sense and cost you your community. The decade where money was so tight that presence was the only thing you could offer and you didn’t because you were too stressed and too busy.
Money is a tool. It’s a genuinely useful tool, but somewhere around your mid thirties, for a lot of men, the tool starts using the man. And by the time you notice you’ve organized your entire life around acquiring something that was supposed to serve your life, not run it. So ask yourself, what are you trading right now?
And is it worth it? Not in theory, actually, specifically. What is money costing you that money [00:17:00] cannot replace? What is money costing you that money cannot replace?
Regret number eight, postponing the life they actually wanted to live. Travel, adventure, novelty, excitement, experiences that pull you out of the ordinary and remind you that the world is genuinely enormous and magical and strange and worth showing up for men, almost universally put this off the trip to Japan becomes someday the sabbatical, always two years away.
The experience they’ve been meaning to have sits on a list that keeps getting longer and less urgent. Researchers call this the someday fallacy, the deep irrational belief that the constraints we face today are permanent and that a future freer version of our life is just around the corner, except the corner keeps moving.[00:18:00]
Robert was 71 when he told me he’s always wanted to walk the Camino de Santiago. He’d been saying it for 25 years. He’d been to Spain twice on business. Got within 200 miles of the starting point. Both times his knees were shot by then, he couldn’t do it anymore, not physically. He got quiet for a long time after he said that, and then he said, I kept waiting for permission.
I don’t know who I was waiting for permission from. Nobody’s coming to give you permission. The life you wanna live is available now. Or it may not be available at all, so let this be your permission for what it’s worth, I hereby right now give you official permission to live the life you want to period.
Regret number nine, having nothing outside of work. I see this one all the time. Men who build their entire [00:19:00] identity around their career face a very specific crisis. When the career slows down, gets disrupted, or ends, because identity doesn’t transfer, the expertise, the status, the sense of purpose, those don’t automatically relocate into the next chapter of your life.
You have to bring something with you. The men who retire well, who actually enjoy the thing they spent 40 years working towards are almost universally the ones who had something else going. A creative practice, a sport, woodworking, cooking, photography, music coaching, youth sports leagues, building things with their hands, something that engaged them for its own sake, not for what it produced professionally.
Gary was a project manager for 30 years. He was brilliant at it. Retired at 62, fully funded by every measure ready to retire. He called me eight, eight months later. He said [00:20:00] he’d watched more television in those eight months than he had in the previous decade combined. He wasn’t depressed exactly. He was just empty, languishing.
Nothing to be good at, nothing to improve. Nothing to look forward to on a Tuesday morning. No goals, no purpose. Your hobbies are not a waste of time. They are in some ways, the whole point. That’s where you exist as a person rather than as a function
and regret.
Number 10, not fully living the life that was right in front of them. This is the one that gets me every time. It’s not that men look back and say their lives were bad. Most of them say there were genuinely good years. Good marriages, good kids, good moments. This regret is more specific and more painful than that.
They were so locked into the future so perpetually in planning mode, so chronically [00:21:00] optimizing for what came next, that they experienced the actual present as a throughway, a means to something else. So much so that they never learned to enjoy the present moment. The vacation they spent mentally at work, the kids’ birthday party they attended in body, while their brain was three time zones away the Saturday morning, they could have just been there with their family in an ordinary moment that they would now give almost anything to have back research on older adults showed that many of them experienced what psychologists call diminished savoring.
They were simply not paying attention to their own happiness while they had it. They were focused on what they had to do, what they hadn’t finished, what was coming. They arrived at 65 and realized they’d been in a hurry their entire lives, and they couldn’t quite reconstruct what they’d been in such [00:22:00] a hurry about.
Being present is not a personality trait, it’s a skill, and it’s the one most men never practice because no one tells them they need to.
The way forward. Okay, so here’s what I want you to do with everything you just heard first, please don’t turn this into shame. That’s the wrong response, and it’ll send you backwards.
The point is not to feel terrible about the choices you’ve made. The point is to see the pattern clearly enough that you can start making different choices while there’s still time to make them. Because here’s what I want you to understand, and this is the part that actually matters. Every single regret on that list is downstream of the same handful of operating strategies, emotional suppression, pride driven isolation, chronic future orientation.
The belief that needing connection or support is weakness. [00:23:00] The belief that your value is entirely tied to what you produce. These are not character flaws. They are learned patterns, deeply learned, culturally reinforced, sometimes adaptive in some contexts, but costly everywhere else. The good news is because they’re learned, they can be unlearned or at least interrogated, and where they can’t be fully undone, they can be interrupted and questioned.
That’s what this work is not fixing you. You’re not broken. It’s giving you better data about your own inner landscape so you can run a different operating system. There’s a framework I use with coaching clients that I call the inner board meeting. You’ve got a CEO inside you, a grounded values driven decision maker.
Who knows what actually matters to you. You’ve also got a director of defense. That part that protects through anger [00:24:00] control or withdrawal. You’ve got a VP of emotions, the part that’s carrying your needs, your fears, your longings, your stress, your love. Most men have their director of defense running the whole company.
The CEO is in there somewhere, but he’s been overruled so many times. He stopped showing up to the meetings. The work is getting the CEO back into the room and then keeping him there as much as possible.
Here’s the one thing I want you to do this week. Just one. Pick the regret on that list that hit the hardest, the one where you felt something tightened in your chest when I described it.
And ask yourself, what is one thing I could do in the next seven days that moves me even slightly in the right direction? Not a massive transformation, not a declaration. Just one action. One little step. One conversation. You’ve been avoiding one phone call to a friend. You’ve been [00:25:00] meaning to reconnect with.
One honest moment with your partner about how you feel. One morning you decide not to check your phone. Small, consistent actions rewire the brain. That’s not a metaphor, that’s neuroplasticity. Repetition builds new neural pathways. You don’t need a life overhaul. You need reps. You’re not out of time, but you’re also not ahead of schedule.
And here’s the funny thing, guys usually do absolutely nothing about regret. They just marinate in it, lie awake at 2:00 AM brain running its greatest hits. Every conversation that went sideways, every version of themselves. They kept meaning to become every time they knew what they needed to do and just didn’t.
It’s like a highlight reel, except nothing’s a highlight. And the kicker, most guys never actually do anything about it. Not because they don’t want to, but because the options are limited. [00:26:00] Real coaching costs, real money therapy has a three month waiting list, and their buddies are, let’s be honest about as emotionally equipped to help as a golden retriever.
Loyal, but not great with emotional nuance. To quote the movie, say anything the world’s full of guys. Don’t be a guy, be a man.
So here’s what Jori and I just launched, and yes, I’m going to say it out loud. They’re psychologically trained AI coaches and they blew me away. They are awesome. I have spent months building these.
My frameworks, my 30 years of research, books, podcasts, articles, exercises, juries, 20 years of clinical training. Everything we actually use with real clients. There’s three of them actually proxy. He for Men Proxy, she for Women Proxy. We for couples available 24 7 in your pocket. The proxy is [00:27:00] short for proximity because we’re trying to get closer to ourselves and to our loved ones.
The goal is connection, and this is not a chat bot telling you to just breathe. It’s not a motivational quote dispenser. It’s actual coaching conversations built on emotional intelligence, my inner board meeting model, attachment theory, nervous system regulation, positive psychology, stress management, anger management, and so on.
The real stuff delivered in a format that does not require you to schedule three weeks out and clear your Thursday afternoon. Is it the same as sitting across from me in a coaching session? No. But is it better than doing nothing while Regret keeps running? Its little 2:00 AM film festival in your head?
Yeah, by a lot. It’s like having me in your pocket always available. Always on. Honestly, in some ways it’s better than I am because it has a better memory and it’s not even close. My goal [00:28:00] now is to look for ways to combine the AI coaches with human coaching. If you think you might be interested in a coaching group that meets virtually once a month where you get access to the AI coach in the meantime, 24 7, email me at john@guidetoself.com and I’m gonna start a waiting list and put this coaching group together.
I think it can be phenomenal. And here’s the kicker, you can try all these coaches for free. Just go to proximity coaching.com. Proximity coaching.com. It’s built for the work you keep saying you’ll get to and now’s a pretty good time to actually get to it.
Alright, that’s the episode. If something today landed, if there was a moment where you thought, yeah, that’s me.
I’d love to hear about it. Email me at John at Guide to Self or find me on Instagram at the evolved caveman and if this episode was useful. Please share it with a man in your life who you think needs [00:29:00] to hear it. That’s the whole point. Get this stuff outta the self-help aisle, into the actual conversations between real men.
Until next time, have the courage to do your inner work so when you get off this rollercoaster of life, you do so without regret. Until next time, this is Dr. John signing off.
Want Fewer Regrets and Greater Connection? Start Here…
😡 For info on Dr. John’s Ultimate Online Anger Management Class (which has over 25,000 graduates!), visit his High Performer Shop.
🧠 Top tools for emotional mastery and high tech execs from the best executive coach in the San Francisco Bay Area:
💬 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 emotional mastery, relationship skill, inner peace & real strength on one of the best podcasts for high-performing men who still feel dissatisfied in life:
🌱 Joree’s expert work on mindfulness, therapy & transformation from the best therapist for women near you:
💬 A top podcast for women who want to get unstuck in life and make the next 30 years better than the last 30:
🎙️ Journey Forward with Joree Rose Podcast
🧠 Need to improve how quickly and effectively your company adapts to change (AI adoption, layoffs, reorgs)? Check out the new TetheredConsulting.com for a revolutionary approach to change management.
🧠 Want to explore a cheaper, faster, more powerful path to individual evolution and improvement? Test out our new AI Coaches based on decades of our material at ProximityCoaching.com
Dr. John Schinnerer, Men’s Leadership Coach: All right. Thanks guys.
Recent Comments