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Five Years Into Becoming an Overnight Success

Five years ago, I grabbed a yellow legal pad and wrote down a vision for what I wanted my life to look like. Not what any influencer, “thought leader,” or my business partners thought I should want. Not what society says a 47-year-old man should have by then. But what I really wanted.

And here’s the crazy part: today, every single thing I wrote down has come true.

But here’s the catch: this is when it gets even harder.

This is when most guys quit.

When the vision starts demanding more; more risk, more spending, more scaling, more conviction. When you’re not getting any younger. When your kids are moving out. When most men your age are starting to slow down. That’s when you have a choice to lean into the dip or pull out. That’s when you find out if you’re really built for this, or if you were just dabbling.

The Trouble With Midlife Success

When I first had the idea for Midlife Male, I was a partner in an insurance firm. On paper, life looked great. But like a lot of middle-aged men, my professional expertise and my personal passion were pulling in opposite directions.

And here’s the truth nobody says out loud: midlife “success” doesn’t always feel, look, or live like success.

I couldn’t just quit. I had equity, a book of business, two private school tuitions, cars, mortgage, “health club,” travel teams, summer camps, and social obligations stacked up like Jenga pieces. Walking away would have been galactically irresponsible.

So I did what most guys sadly do; we recommit to the thing we don’t love so we can buy time for the thing we hope we might.

I doubled down on my business and at the same time, mapped out the passion project my career would pay for. And I hired a coach and a therapist to keep me from self-sabotaging everything I’d built.

The Bare Reality

Here’s the part that never makes it to Instagram: none of this came without cost.

I lost my relationships with my former business partners. They were all in, I wasn’t; and eventually, that gap became too wide.

I lost some friends when I stopped drinking and partying. The invitations dried up when I started saying no to the bar and yes to the gym. But I also gained new ones, the kind of men who show up at sunrise, who spot you under a barbell, who celebrate milestones that don’t require a hangover.

There were rough patches with my wife, Kate. Real “what the fuck are you thinking?” kind of confrontations. Because when you start making changes in midlife, it shakes everything up. I was drinking a lot of new Kool-Aid—therapy, coaching, journaling, podcasts, biohacking, wellness retreats. 

And here’s something I need to be 100% transparent about:

I overindexed on the self-help treadmill for a while before I found my balance and learned to master the middle.

Even the good changes are messy. Even the right decisions come with turbulence. Change isn’t clean. And it doesn’t always feel good in the moment.

What Happened in 5 years 

• My Career: I stayed a top producer until we sold the firm in 2020. Pocketed a nice fat check. Not FU money, not retirement money—but enough runway to leave.
  

• The Podcast I started: 200+ interviews, 1M+ downloads, became a newsletter, a book, and a platform with 25k+ subscribers
  

• That Community: I’ve now coached 100 men directly, 1:1. These are relationships  built on trust, commitment, and transformation.
  

• The Fit Life: Best shape of my life at 52. HYROX podium. 4 Everest climbs. Barn gym workouts with Don Saladino. Pool work with Laird Hamilton. More importantly, I can say yes to anything my kids or wife ask of me physically.
  

• My Family & Fun: Road trips, concerts, travel, bucket list experiences, and two college move-ins. I was there. I’ll keep being there.
  

The Bottom Line

Five years later, I’m pacing to be that ten-year overnight success.

And here’s what I need you to hear: most people quit right here. Seven, eight, nine years in. Just before it compounds. Just before it gets good.

Because it’s hard. Really hard.

Hard to live life by design instead of default. Hard to keep going when the finish line keeps moving. Hard to do the shit you say you want to do. Harder still to do it well enough that anyone notices.

Success in midlife is expensive, risky, and often lonely. And it often doesn’t feel like you’re winning while you’re in it. 

But this is the moment that separates dabblers from doers.

This is when you have to double down.
This is when you have to bet on yourself at the exact moment everyone else is winding down.

I’m not winding down. I’m just warming up.

In Health,

Midlife Male
52. Husband. Father. Entrepreneur. Coach. Student of the game.
Still walking the walk.

PS:  If you’re looking for some support, a guy who’s been there, done that and has the real life experience to help you get from where you are to where you want to go, just reply to this email and we can set up a quick call. I’m booking 1:1 coaching clients for 4th qtr and ‘26 right now.

MIDLIFE LATELY (Click the pic)….

Recommendation:

Recommendation: Seth Godin’s The Dip nails it: the hardest part isn’t the end, it’s the choice. Better one? Quit too soon, settle, slide into average. Better two? Lean in, push through the dip, and come out the other side stronger, sharper, better. That’s where the difference between midlife mediocrity and midlife mastery gets made. Super short and impactful book. Check it out.

The Middle is Sponsored by Swimclub

Kate and I struggled with fertility. Fortunately, we were blessed with two healthy sons. Our boys are grown now, but I often think about how different our journey might have been if a product like SwimClub had existed back then.

There are very few outlets for men to openly talk about sperm health, and even fewer products designed specifically for us. SwimClub is the first comprehensive supplement built for men on the path to fatherhood. It combines the right research-backed ingredients at the right doses to support sperm health, fertility, and confidence along the way.

SwimClub is what I wish I had: effective, efficient, and built for men on this journey. Whether you’re just starting to think about having kids or you’re deep into IVF, SwimClub takes the work off your plate and makes the road to fatherhood a little easier—so you never have to feel alone or helpless again. Check it out here.