Turning 40+ into a Flex
A conversation with Jon Finkel, the world's most sophisticated meathead
👋Hello, my friend. I’m back on the podcast horse! It’s been a little while, but I’m psyched to bring you what I thought was a really great conversation that I recently had with Jon Finkel — an author, newsletter writer, and quite possibly the world’s most sophisticated meathead.
Jon is a returning guest, a longtime buddy who I connected with on Twitter, and someone I always walk away from feeling a little more energized and inspired — especially when it comes to navigating this complex, occasionally exhausting, but potentially very rewarding stage of life known as middle age.
Let’s get into it.
The Midlife Balancing Act
One of the big things I’ve been thinking about lately — and something Jon and I really dug into — is the idea of balance in midlife.
To me, it comes down to juggling three balls in the air at once:
Health & Fitness
Relationships (especially parenting)
Career
You could probably throw in things like hobbies, community, or spirituality too — but these three feel like the main ones. And the hard part is… you can’t let any of these balls drop for too long.
Jon does an awesome job of managing that balance — and doing it with humility, consistency, and humor. He’s someone who’s still very much himself, even as the years roll on. You get the sense that he’s been “keeping it real” since about age 14 and hasn’t looked back.
Health & Fitness: Staying in the Game
Let’s start with health and fitness.
Jon’s approach is pretty simple — and that’s part of what makes it powerful.
“The secret is, I didn’t stop.”
At 47, Jon is still benching over 300 pounds. (Not remotely relatable to me personally… but pretty damn impressive nonetheless). He’s competing in masters swim meets. He plays pickup hoops every Friday morning. He’s lifting weights in his garage (aka “The Flex Factory”) multiple times a week. He’s tracking his lifts and his times and improving. Pretty impressive stuff at 47.
He’s not training for the cover of Men’s Health — he’s training so he can do things. Compete. Stay agile. Move well. Feel good.
Competition matters.
We talked a lot about how important it is to have something on the calendar to train for. For Jon, that’s swim meets. For me lately, it’s been things like golf tournaments, 5k’s with my kids, and the occasional overly serious game of pickleball. But I honestly need to up my game here — and I’m looking for ideas.
The point is: competition brings purpose to the process. It gives your workouts structure. It helps you show up even when you don’t feel like it. And it makes it all more fun.
Mobility: The Underrated Key to Midlife Longevity
This part of the conversation hit home for me.
At one point, Jon told the story of getting back up on the starting blocks for a swim meet after years away — and realizing he couldn’t touch his toes. Not even close.
He called himself a “rickety lawn chair” and admitted he had totally let his mobility go. So he started the Knees Over Toes program by Ben Patrick — and it’s been a game changer.
His flexibility has improved materially, and it’s having positive ripple effects in some unexpected places. He’s now doing full split squats, grabbing the rim again on the basketball court, and putting his shoes on without groaning.
Since our chat, I’ve gone down the rabbit hole myself — researching mobility routines, checking out YouTube workouts, and discovering that there’s quite a bit of great free content out there if you don’t want to pay for a program.
Takeaway: If you want to keep showing up — whether it’s on the court, in the gym, or just walking your dog without pulling a hamstring — mobility matters.
Relationships: Meeting Your Kids Where They Are
This was one of my favorite parts of the conversation.
Jon and I are both lucky enough to be dads to both boys and girls (1 boy, 1 girl in Jon’s case; 2 boys, 1 girl in my case). And we talked about how different those relationships can be — especially as your kids start to get older.
With our boys, it’s often easy. Sports are the shared language. You can shoot hoops together, talk baseball, go play nine holes, watch SportsCenter. The bonding happens almost accidentally.
With daughters, it can be different. In a lot of cases, dads need to be more intentional. To work a little harder to find common interests. To make room for that shared downtime, which can be so valuable.
I mentioned how my daughter and I recently made a list of activities we could do together — tennis, trying new restaurants, maybe even taking a class together. Nothing crazy, maybe just once a month… but the idea is to be a little more intentional about it before she’s a full-on teenager and I only get to see her in passing. I want to make sure the foundation of our relationship is strong before we get there — and it’s coming fast.
Jon talked about going on nightly walks with his daughter, who’s in the full-on teenager phase — just giving her space to talk. No phones. No agenda. Just being there.
That idea — being there — kept coming up. Whether it’s showing up at school drop-off, coaching your kid’s team, or just hanging around enough that they know you’re available — it’s powerful.
It sounds simple, but in this era of maxed-out schedules and constant distraction, it’s a real practice.
Career: The Portfolio Approach
On the career front, Jon is a great example of someone who’s built a life around his strengths and interests — and who’s made it sustainable.
He writes books — everything from a biography of Macho Man Randy Savage to a personal favorite of mine, 1996, which revisits the year Jon and I both graduated high school through the lens of pop culture and sports.
He publishes a great newsletter geared toward dads called Books & Biceps, where he shares thoughts on training, mindset, and (of course) reading.
And he’s recently gotten involved in Midlife Male, a media brand and community focused on helping men thrive in — you guessed it — middle age. They’re doing events, podcasts, and weekly newsletters for a growing audience.
This is what I often call a “portfolio approach” to a modern career. It’s not about one job title or one paycheck. It’s about building something that reflects who you are, offers flexibility, and creates value for others.
Jon’s doing that in spades. It’s fun to see. And pretty inspiring, too.
Final Thought: Keep It Fun
More than anything, this was a fun conversation.
Sometimes, conversations about middle age can veer into the doom-and-gloom zone — all about burnout, midlife crises, or “surviving the grind.”
But Jon’s perspective is a reminder that this stage of life can also be deeply enjoyable — if you’re healthy, connected, and engaged in things that matter to you.
We laughed a lot. We shared notes on workouts and parenting and vacations. And I left the conversation feeling energized.
If you want to hear two dads in their late 40s chop it up about how to stay strong, stay sane, and stay in the game — I hope you’ll give it a listen.
Links to listen & watch:
Apple Podcasts:
Spotify:
YouTube:
Have a great week… but before you go…
Content Diet
All-in Podcast AI Summit
I’m currently bingeing the All-In podcast’s multi-episode AI Summit. Definitely taking some of it with a grain of salt because it doesn’t lack for political bias… however, there is quite a bit of value here, and so far, one conversation in particular has really jumped out to me.
That was with Chris Power, CEO of Hadrian — a company building AI-enabled factories in the U.S. It starts at the 18:24 mark of the video below (we’ll see if I shared it correctly so that it goes directly there).
If you’re:
1/ worried about AI being a massive job destroyer
2/ wondering how your kids will ever be able to get jobs in this new world
3/ interested in hearing about how the U.S. can realistically re-industrialize/bring manufacturing industries back on-shore…
…this presentation is eye-opening.
I’m feeling all bulled up on AI & America’s potential (and the job market for my kids) after listening to this.
Have a great week!
Greg