Miserable Midlife Millionaires

PLUS: What Jon Learned Writing "Mean" Joe Greene's Autobiography, 'How I See It' with Sean Hoess, The 28-Minute Reset that Actually Works, & More

Author

Greg Scheinman
October 19, 2025

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Morning, Greg here!

Welcome to Midlife Male, the fastest-growing, #1 newsletter and lifestyle brand for men 40+. In today’s issue we’ve got my Viewpoint on the not-so-complicated reason ‘successful’ men aren’t happy, Jon’s Manologue on the lessons he learned from NFL legend ‘Mean’ Joe Greene, our How I See It with Wanderlust and Eudemonia founder Sean Hoess, and, as always, our 6F recs. If a fellow MLM reader shared this with you, subscribe here:

Why Many Wealthy Midlife Men Are Unhappy

I have a term for rich men over 40 who are unhappy. 

I call them 3M guys: Miserable Midlife Millionaires. And I know a lot of them.

Now, the miserable part isn’t exclusive to the millionaires. But statistically speaking (and you know how I feel about statistics), after a certain point of income, happiness levels no longer increase. And this I can say with 100% certainty: money does not buy happiness.

But if you ask me whether I’d rather be middle class and miserable or rich and miserable, that’s the easiest Better One or Better Two choice ever. I’d rather be rich and miserable. At least you’ve got resources to work with. But the point remains: the misery is real, and it cuts across income levels.

So why are these guys who seemingly have it all so unhappy?

The simple answer is usually because they’re just not doing things that make them happy.

It’s not that they don’t know what those things are. Almost every guy I talk to knows exactly what he wants: learn chess, travel, get involved with a charity, spend more time with his kids, pick up golf, play less golf, work out, see a movie, reconnect with some old friends, go for a walk.

The frustration comes not from lack of clarity, but from all the…

4 Awesome & Surprising Things I Learned Writing “Mean” Joe Greene’s Autobiography

Tuesdays. 3pm. Mr. Greene’s house.

That was the standing time and location that I sat with one of the most iconic figures in sports history to discuss his life for our book, “Built By Football”. Mr. Greene happened to be “Mean” Joe Greene, one of the greatest Pittsburgh Steelers and NFL players of all time. I jokingly referred to it as my version of Mitch Albom’s book, Tuesdays with Morrie, except mine was Tuesdays with “Mean” Joe.

We met every week for about four months. I was 39 and Mr. Greene was 71 at the time, but he was still every bit of 6’5”, well over 250 pounds, and imposing.  I was lifting heavy back then, proud that I’d built myself up to about 210 at 5’11” and yet, when I first met him I felt like a little kid. When we shook, his hand swallowed mine whole, like he was palming a Hot Wheels car.

I am from Boston and Joe grew up in a small town in Texas. I peaked as a high school punter and back-up fullback, while he peaked as arguably the greatest defensive lineman ever. Our ages. Our backgrounds. Our dimensions. None of them were similar, but we had a lot in common, talking for hours, with the chit-chat often bleeding into our official “autobiography interview” time.

Over iced tea in his family room, with his NFL Hall of Fame bust looking on, we’d sit across from each other on thick, comfortable couches and we’d talk about anything and everything. Life, basketball (especially Bill Russell and the Celtics), mentoring, teaching, parenting, and of course, the NFL and the Steelers. It was an absolute career highlight that I will cherish forever.

As my kids have gotten older and I’ve gotten deeper into my career, I’ve found myself retelling pieces of his story to my kids or to friends regularly. While you know about Mean Joe because of his 4 Super Bowl wins and Hall of Fame status, you don’t know what it took to get there. 

In fact, that was one of the main tenets of our agreement to write his autobiography together. He didn’t want to talk about the Steelers Super Bowls anymore. They’d been analyzed and discussed in documentaries a million times.

Our book was going to be about the road he took to get there. The things he hadn’t talked about. The good stuff.

With the NFL season rolling, I thought it would be cool to share four of the biggest pieces of wisdom on the rarity of greatness, giving credit to others, harnessing failure and more that I learned from Joe. Trust me, you’ll be sharing these stories with your kids and co-workers:

How I See It with Sean Hoess

Eudemonia means “life well lived.” I like that. Last year, I went to the inaugural Eudemonia Summit in Palm Beach because, duh, I want a life well lived. Simple concept, right?

I called up the founder, Sean Hoess, who also created Wanderlust, and said, “Hey, I want to bring some guys down.” He was cool enough to give me a Midlife Male code.

The weekend was loaded: workouts with Don Saladino, a keynote from Andrew Huberman, morning yoga, healthy food, and a crowd that was about 90% women – fit, healthy, and all in workout clothes. Not complaining.

There were also talks from Dr. Mark Hyman, Dr. Michael Breus, and Dr. David Rabin on topics that hit home for me at 52: sleep, longevity, anxiety, and functional health. What stood out most was how accessible everyone was. I’ve actually become friends with Breus, who’s helping me with my sleep apnea, and Rabin, whose Apollo Neuro device I now use regularly.

Now, I’ll admit, I skip most of the hardcore biohacking. I passed on Bryan Johnson’s session and tuned out of Huberman’s deep science talk until the last five minutes when he finally shared three or four things I could actually do to improve my life. That’s the stuff that matters. Not majoring in the minors. Not getting lost in the weeds. I don’t personally need 30 talks in three days. I enjoy these things because I want to stay active, stay engaged, and surround myself with healthy, happy, forward-thinking people.

This year, I’m going back. I’ll be moderating a panel on menopause from the male perspective—manopause, if you will—with Julius Thomas, Dr. Gregory Scott Brown, Shawn Wells, and Dr. Kwado. I’m also co-leading a three-mile morning ruck.

A few weeks ago, Sean and I hopped on Zoom because we’re both trying to get more middle-aged men to show up. What we’re seeing is a lot of guys either doing nothing… or trying to do everything.

And here’s the truth: walk around these festivals and most of the guys look like a mix of biohacker poster boys and Burning Man disciples. What Sean and I talked about—and what I’m all about—is mastering the middle. We’re just normal men who care about health, wellness, longevity, and sustainability. We’re solid husbands, fathers, and friends. And let’s be honest, being around beautiful, healthy women shouldn’t be a hard sell.

Eudemonia has a lot to offer: great brands, great products, and valuable knowledge we can actually use. Things that help us refine our Midlife Action Plans. There’s real value in that.

The irony? There aren’t nearly enough midlife men attending, but there are plenty speaking; guys like Rich Roll, Arthur Brooks, and Mark Hyman.

My biggest takeaway last year, and what I’m looking forward to again, is simple: being in Palm Beach with my wife. Working out. Learning. Listening. And choosing exactly what I want to do, when I want to do it.

So enjoy this week’s How I See It with Sean Hoess. He’s one of us, building something special, and I want to support it.

In health,

Greg

Raising Thinkers in the Age of Idiocracy

If you’ve got kids, read Zack Kass’s How to Raise a Successful Child. It’s one of the smartest takes on what’s really happening to the next generation.

Attention spans are shrinking. Kids scroll more and think less. Schools keep lowering the bar. Kass calls it “idiocracy,” when people stop using their minds because they think they don’t have to.

The bright side: some kids are excelling like never before. More are taking advanced courses, learning languages, and building real skills. The gap between average and excellent is just getting wider.

Our job as parents is to keep our kids on the right side of that line. More reading, more doing, more conversation. Less screen time. Help them stay curious, focused, and independent.

The 28-Minute Reset That Actually Works

Guys always ask me where to start. Start here. Your lymphatic system is your body’s hidden detox engine. When it’s sluggish, you feel heavy, inflamed, and tired. When it’s flowing, your body heals, burns fat, and your energy skyrockets. I’ve been doing Jules Horn’s 28-minute fascia + lymph flow sequence for the past month, and I’m hooked.

Yeah, it looks a little silly at first, but it works. It pumps lymph fluid, releases fascia restrictions, reduces inflammation, resets your nervous system, and boosts metabolism naturally. It’s the perfect warm-up, recovery, or daily reset. You can do it anywhere.

The Rise & Fall of CrossFit: A 15,000-Gym Empire for Sale

Chances are a bunch of you reading this have tried CrossFit at least once and some of you may be diehards to this day. But whether you’ve entered a box or not, this video from entrepreneur Michael Girdley on the rise, fall and future of CrossFit is fascinating from a financial perspective. It’s wild how fast the sport grew, how much money it once took in, and how quickly perception of the workouts and culture changed. This is a great 15-minute video.

Why My Dogs Eat Better Than I Do

If you love your dogs as much as we do, you want them healthy, strong, and living as long as possible. That’s why we switched to We Feed Raw. After years of feeding the standard kibble, I started reading about raw food diets and how they improve digestion, immunity, and energy.

Roxy and Riley have been on it for almost a year—they’re thriving. It’s simple: go online, fill out a quick profile, and fresh raw food shows up monthly. Healthier dogs. Easier routine. Happier home. Get 30% off here.

The Perfect Button-Down for Men Who Hate Button-Downs

Simple. Clean. Great material. The Dress Draped Twill Shirt from Buck Mason nails it. Not formal. Not casual. Just that perfect fit that makes you look sharp without trying.

We’re T-shirt guys, sure, but sometimes you want to step it up. This is that move. The shirt drapes right, feels premium, and looks even better after a few wears. Check it out here.

Fitness Meets Friendship on the Pitch

Community and connection surrounded by great people—that’s fun to us. My good friend and former Houston Dynamo star Mike Chabala, founder of SPHERE, invited me to join the largest community workout of the season inside the Dynamo’s Shell Energy Stadium.

First half: a 45-minute SPHERE fitness session led by pros and alumni—bodyweight and endurance work, no soccer.

Second half: a mindfulness and optimism session led by Case Kenny. Then cold plunges, product activations, and locker-room hangouts to close it out.

If you’re in Houston, come join us on the pitch 10/23. Check-in starts at 6:00pm.

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