You don’t actually want what you think you want.

Give that a minute and sit with it. 

We all have that guy in our circle. Or maybe he’s got the bigger office down the hall from you. Or you follow him on social media. Or see him at the school events.  The one who never slows down. The one building the empire, closing the deals, stacking the accolades, always on to the next thing. 

You watch him and part of you wonders what that must feel like. And at some point, standing around with your friends with a drink in your hand, somebody says it: Man, if I had his money, I would do this, this, this, and this.

But here’s the truth: You’re not going to have his money. You’re not going to have his life. Because you’re not willing to do what he does to get it. And honestly? Neither am I.

That’s not an insult. That’s just reality. 

Everything costs something. The podium. The big exit. The body. The empire. None of it is free and none of it is easy. 

Wanting the result is not the same thing as being willing to pay the price. It can’t just sound good. It can’t just look good on paper or make for a great story at a dinner party. If you want real success, the kind that actually means something,  you have to be willing to do the work. Not just the fun parts. Not just the parts that make great content. The hard parts. The uncomfortable parts. The days that flat out suck. You have to want the process, not just the prize. You have to be willing to embrace all of it, even the grind, because that’s actually what makes the outcome worth anything.

The problem that I’ve found is that when most guys hear that, they immediately think: then I’m a failure. I’m not ambitious enough. I’m not built for the big game. How am I going to be perceived by other guys, friends, colleagues? 

They feel like they have to keep performing the version of success they think they’re supposed to want, because admitting they want something different feels like weakness. Like they’ve tapped out. Like they’re not serious.

Maybe what you actually want is something different. And you’ve spent years being too afraid to admit it because admitting it and comparing it to the societal norms for men, kinda looks like you’re selling yourself short.

But what if it’s the opposite? What if it’s actually a better long game for you? 

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I spent almost fifteen years as a partner in a big firm. And for a long time I told myself the story that I was building toward something, toward their version of the mountaintop. They sold me on it, and I bought it… For years.  

But eventually I had to sit with a truth I’d been avoiding: my version of success was never the same as my partners’. My ambitions, my goals, my standards, they were never going to align with what it was actually going to take to get to their level. And we were never going to close that gap.

I remember one of the guys saying to me when we were being acquired  “This opportunity is like being offered the greatest deal on a Bentley!”.  

My reply: “Yeah, but I’m not in the market for a Bentley.”

You can sit there and walk me through the upside all day. The acquisition opportunity. The new accounts. The bigger prospects that can lead to the bigger commission checks. The prestige. And I would sit there across with this kind of blank look on my face thinking: I don’t want that. Not because I can’t. Not because I’m not capable. But because the life that comes attached to that deal, the one you have to actually live to get there,  is not the life I want to live. Their way of living would have put me into a decade of therapy, or kept me in the bar after work nightly. And my attitude, my vision, my version of winning, would have slowly poisoned their “corporate culture”. Neither of us was wrong. We were just not the same.

You have permission to opt out of someone else’s scoreboard.

So I did something that felt uncomfortable at the time but turned out to be one of the most clarifying things I’ve ever done. I wrote down what I actually wanted.

I wanted to stay at the top of my game; not number one, not grinding at my desk until midnight, but in the top tier. Keep my clients happy. Sign just enough new ones to avoid going backwards and keep management off my back. Because that life lets me coach my kids. It let me be home for dinner. It lets me be present for the stuff that doesn’t show up on a revenue report but matters more than any of it.

I wanted to be fit. To compete. To train hard, but not at four in the morning every single day just to squeeze it in around someone else’s schedule and someone else’s priorities.

I wanted a creative outlet. Something that was mine. Which is what Midlife Male became. A place to write, to think, to serve other men who are wrestling with the same questions I was asking myself.

As I kept walking down that path, instead of the one I thought I was supposed to be on, what happened was that I got happier, healthier, wealthier (in more ways than just the dollar), and started having more fun again (the right kind!). 

And here’s where I ended up: I’ve gone from a firm with 200 people to a small coaching practice. A group of ten-plus guys, working individually, talking weekly, sometimes daily, about the real weight and nuance of middle age. Men who have also become friends. A newsletter that now reaches almost fifty thousand of you every week and generates real revenue. Brand partners I actually believe in and use myself. Adventures with other solid guys doing things worth doing.

And here’s something else: you can build a million dollar business that produces a multimillion dollar lifestyle. But here’s what it actually requires. Discipline. Saying no to the things that sound good but aren’t yours. Letting go of the idea that more is always better and replacing that with something harder and more honest: better is better.

I’m fifty-three. And the way I see it, fifty-three to seventy are the most vital years of my life. So the question I keep coming back to is: what do I actually need to live at that level, with that kind of energy, that kind of freedom, that kind of presence?

Not “fuck you money.” Real freedom. Waking up without an alarm. Going to bed when I want. No obligations that aren’t mine by choice. Being able to meet my kids where they are, when they need me, without having to check a calendar or ask permission. None of that requires a private jet. All of it requires clarity.

I have close friends who built great companies and sold them for serious money. They do everything I just described,  and they do it on a Gulfstream and take their families to Wimbledon for the finals. I love that for them. I don’t begrudge it or judge it in the least. Genuinely. That ship has sailed for me. In fact, I never even boarded it. That’s not the life I’m designing for now and my future. And being honest about that, really honest, out loud, and on paper, changed everything.

Too many men get stuck performing the version of ambition they think they’re supposed to want. But designing a life on your own terms isn’t settling. It’s one of the hardest, most intentional things you can do. 

For every giant agency there’s a great boutique shop doing exceptional work and sleeping well at night. For every massive media company there’s a newsletter like this one, growing steadily, serving a real audience, meaning something to the people it reaches.

The work isn’t grinding harder after the thing you think you’re supposed to want.

The work is getting ruthlessly honest about what you actually do.

Because sometimes the thing you’re really chasing isn’t a number or a title or an exit or a score. It’s a feeling. You can’t always put your finger on exactly what it is. You just know it when you feel it.

And that’s what we need to be honest about, with ourselves, first.

Here’s the one thing you should walk away with:

Write down what you actually want. Not what sounds impressive. Not what gets nods from other men. What you actually want. Because until you do that, you’re either chasing someone else’s life or performing a version of success that was never yours to begin with.

Then start living that way. One day at a time.  

In Health, 

Greg Scheinman

Founder, Midlife Male

Husband. Father. Entrepreneur. Coach.

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