I’m 37, and by almost any objective measure, I’m a very lucky guy.
I’ve rarely been sick. I have great friends. I’ve had a pretty good run romantically, been loved by women I genuinely cared about, and eventually met someone I thought was an angel. I wasn’t just in love with her. I was in awe of what a wonderful person she was.
After some difficult years trying to conceive, we had a beautiful son whom I absolutely adore.
Professionally, I’ve done very well. I make a lot of money, certainly by most people’s standards. I’m not wealthy in the sense of being financially independent, but I have a level of comfort and security that most people would consider a privilege.
Here’s the strange part.
If you asked me how my average day is, I’d probably say **7/10**. And those days have genuine 10/10 moments, especially playing with my son.
But if you asked me how the past month was, I’d probably say **5/10**.
Because when I look back, I start thinking about everything that’s missing.
I’ve gained weight. I’m not as fit as I used to be. I don’t feel as sexually desirable anymore. I feel like I’ve lost some of my humour, spontaneity and sense of adventure.
My wife and I have struggled with intimacy for years, particularly through our fertility journey and now parenthood. We’ve both changed physically. I miss the excitement and feeling of being wanted.
I look around my house and think it’s not the beautiful home I imagined having. Sometimes even the mess bothers me disproportionately. Why isn’t everything nicer, cleaner, better?
I think about the fact that I didn’t take my son swimming this week or read to him enough.
And I know how absurd some of this sounds given how fortunate I am.
But here’s something else I should admit.
**I never really wanted to be just successful. I wanted to be extraordinary.**
I wanted enormous wealth, admiration, attention, sexual desirability, the whole thing. I wanted to be the big man in the castle.
Not the guy who earns enough to eventually afford a nice house and retire comfortably. I wanted the kind of wealth that fundamentally changes what’s possible in your life.
Maybe that’s vain. Maybe even a little narcissistic. But it’s what I wanted.
And somewhere along the way, I exchanged the possibility of that extraordinary outcome for a very well-paid, relatively secure career.
Which raises uncomfortable questions.
Did I settle? Did I miss my opportunity? Was I simply not good enough?
The strangest thing is that **the happiest I remember being was when I was practically broke, trying to build my own company.**
I sometimes couldn’t afford public transport, so I cycled everywhere.
I was extremely fit, disciplined, ambitious, provocative, funny, sexually confident and full of energy. I could work ridiculous hours, go out at night, wake up early and do it all again.
I’d decided I was going to be a fucking Spartan. And in many ways, I was.
My business wasn’t particularly successful. I was frustrated by that. I had plenty of problems and certainly wasn’t satisfied with my circumstances.
So I’m not pretending those were perfect years.
But I remember one feeling very distinctly.
**I was incredibly proud of the man I was becoming.**
I admired my own discipline, courage, ambition and willingness to fight for what I wanted. Even when things weren’t going my way, I respected how I was conducting myself.
I’ve matured since then, of course. I’ve learned that strength isn’t always about fighting harder. Sometimes it’s knowing when a fight isn’t worth having. Sometimes becoming stronger means accepting your limits rather than trying to overpower everything.
I value that growth.
But I also wonder whether somewhere along the way I lost some of my fire.
I’ve meditated for years. I understand intellectually that everything is impermanent, that comparison can make you miserable, and that there’s no magical destination where you’ll finally be satisfied.
But knowing that doesn’t make the dissatisfaction disappear.
And honestly, I’m not convinced that all my desires are misguided. Maybe I genuinely want to be extraordinarily wealthy, attractive, adventurous and admired. Why should I pretend otherwise?
I suppose the best way to describe it is this:
**I enjoy much of the life I have. But I’m disappointed by the distance between the man I imagined becoming and the man I am today.**
And perhaps the biggest loss isn’t the money, the house or the attention.
It’s that I once looked at myself and felt tremendous pride in who I was becoming.
I’m not sure I feel that anymore.
I don’t miss my old life. I love my wife and son, and I wouldn’t trade them for anything.
**I miss my old self.**
I’m genuinely interested in hearing from men who’ve experienced something similar, particularly those who were extremely ambitious when younger and later settled into successful but more conventional lives.
Did you eventually make peace with it? Did you rediscover that old fire? Did you realise you’d genuinely compromised too much? Or did your definition of success fundamentally change?
I’m not looking for a lecture about gratitude. I know how lucky I am.
I’m trying to figure out whether this dissatisfaction is something I need to overcome, or something I should actually listen to.