The other day, I sat in my car, sore from head to toe, debating a very midlife decision: drop $200 on a massage or buy the sneakers I’d been eyeing online.

My body was screaming for recovery. But there I was, wondering if owning something would feel better than feeling better.

Welcome to the midlife male trap.

The Experience Deficit

Let’s cut the crap: we’re living possession-rich, experience-poor lives.

Look around at your fellow 40+ dudes—we’ve mastered the art of acquisition. The watch collection. The closet full of barely-worn shoes. The garage toys. The endless tech upgrades no one needed.

But the stuff? It doesn’t hit like it used to. We’re running a deficit in the one currency that actually brings joy: experiences that engage us, ground us, and give us real connection.

A 20-year study out of Cornell nailed this. Experiential purchases provide longer-lasting happiness than material ones. Why? Because experiences become part of who we are, while things sit on a shelf. Possessions lose their shine. Memories don’t.

As lead researcher Dr. Thomas Gilovich put it:

“We buy things to make us happy, and we succeed. But only for a while.”

That $1,000 watch? Cool for a week.
 That $1,000 concert with your kid? Unforgettable.

The Real Luxuries of 2025

The Wall Street Journal recently profiled the new status symbols for men who can buy anything. You know what didn’t make the list? Cars, watches, or tech.

The new flexes: health, sleep, presence, time, deep relationships.

Today’s billionaires aren’t bragging about Rolexes. They’re comparing blood work and competing over who can unplug to coach Little League.

One hedge fund guy put it perfectly:

“I can buy another house. I can’t buy back the sunrise I missed while checking email.”

Translation: the guys who reached the top of the mountain are telling us they climbed the wrong one.

So why are the rest of us still climbing?

Better 1 or Better 2?

When I coach midlife men through this mindset shift, I use a simple tool from your last eye exam: Better 1 or Better 2?

Option 1: Buy the sneakers.
 Option 2: Get the massage.

Which actually makes your life better?

Option 1: Work through the weekend for a bigger bonus.
 Option 2: Take that weekend hike with your closest friends.

Option 1: Another round of drinks with clients.
 Option 2: Finally take that guitar lesson you’ve put off for 10 years.

Nine times out of ten, the answer is obvious. And here’s the best part: when you choose better consistently, your life gets better. It’s compound interest—but for your well-being.

Build Your Experience Portfolio

The happiest, wealthiest guys I know don’t track net worth anymore. They’re tracking what I call their experience portfolio.

Harvard researchers found that even anticipating an experience brings more joy than anticipating a purchase. The planning, the countdown—it’s all part of the ROI.

The Journal of Positive Psychology backed it up: people waiting for experiences (concerts, trips) are happier than people waiting for stuff.

My richest friend isn’t the one with the biggest house. It’s the guy who takes a month off every year to explore somewhere new. Who hits every show his favorite band plays within a hundred miles. Who blocked off every Thursday for lunch with his dad until the day he passed.

That’s wealth. That’s legacy.

The Midlife Pivot

Let’s be honest: we spent our 30s and early 40s stacking wins—career, house, family, financial security. That chapter had its place.

But eventually, the math changes. The ROI on experiences crushes the ROI on possessions.

  • 57% of millennials already prefer experiences over stuff
  • 72% of people feel happier from experiences vs. 44% from material buys
  • Experiences build identity, deepen relationships, and create connection

The data’s in. Experiences > Stuff. Full stop.

The Better Life Equation

So here’s the challenge: for the next 30 days, when you’re about to spend, ask yourself: Better 1 or Better 2?

New watch… or that sold-out concert you’ve always wanted to attend?

Car upgrade… or that photography workshop you’ve been dreaming about?

Latest gadget… or a cooking class with the chef you admire?

Run the test. Choose accordingly.

Back to that $200 decision in my car.

I chose the massage. My body thanked me immediately. My mind thanked me that night with better sleep. My family thanked me the next morning because I wasn’t a grumpy jerk at breakfast.

The sneakers? They’d look great in the closet.

But the massage? That made my whole life better.

Better 2, fellas. Choose Better 2.

 

In health,

Greg

Greg Scheinman is the Founder of Midlife Male. You can follow him on Instagram and LinkedIN

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