This weekend, I flew out to Napa for my client’s 60th birthday. One of the things we’d been working on over the last year is to build more joy into his life. He’s climbed to the top of the professional mountain. He is financially successful and generationally successful. He’s experienced tremendous professional highs and has experienced equally low lows; divorce, mental illness, being a single father, the murder of his best friend.
Celebrating himself has not been something he’s made a priority. And one of our goals has been to change that.
That’s a lesson in itself. Most men don’t struggle to achieve. They struggle to allow themselves to enjoy what they’ve achieved. We stay in build mode. Provide mode. Fix mode. Or we fall into conformity, complacency and redundancy mode.
And somewhere along the way, we forget that joy isn’t something that just shows up; it’s something you have to plan for, commit to, and protect. Joy has to become one of your standards.
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Joy Has to Be Scheduled
He invited 12 friends to join him for a 60-kilometer hike to celebrate his 60th birthday, combining all the things he loves. Nature and the outdoors, as he’s developed a love for hiking over the last 24 months, and has improved his physical condition significantly. His love of conversation, connection, collaboration, and improvement through surrounding yourself with individuals you can learn from and enjoy being around, outside the boardroom, in conferences and conventions.
He brought in an award-winning chef who has literally beaten Bobby Flay on the Food Network, for fresh, organic, healthy, and also indulgent meals and desserts. He rented an extraordinary property with a gorgeous main house, guest houses, a pool, hot tubs, and had a masseuse come in daily.
But here’s the thing, it didn’t have to be Napa. It didn’t have to be a private chef or a big house. The real takeaway is this: someone decided this mattered enough to organize it. To put it on the calendar. To invite the right people. To say, “this is how I want to live.” And then each of us decided that this mattered enough to us to show up, put it on our calendars and live this way too.
Most guys are waiting for life to present these moments. The ones who get to experience them are the ones who create them.
We woke up early and went to bed tired, spending each day waking with the sunrise, beginning at six. Twenty miles the first day, ten miles the second day, along some of the most beautiful trails: Mount St. Helena, Calistoga, Napa.
You Can’t Manufacture Chemistry
But as important as the magnificent views were the conversations that we had and the connections we were making with one another.
This is what most men are missing. Not more information. Not more three-hour masterclass podcasts. Not immersing themselves into more self-help books. They’re missing shared experiences. Movement. Effort. Time together doing something real.
That’s how growth happens for me.
I knew two people on this trip prior to going; my close friend, Sterling Hawkins, who I’ve hiked with, adventured with and spoken on stages with, and my client, who I had introduced to Sterling two years ago at the beginning of his journey and our work together. He joined Sterling on his trip last year through Machu Picchu and they’ve become close friends.
Everyone else, it was my first time meeting them.
When I landed at the airport in San Francisco, Sterling was at my gate. He introduced me to Jason Harris, a retired lieutenant colonel in the Air Force. He’s flown over 400 combat missions. We were picked up by one of my client’s friends, and within minutes, the four of us were talking and laughing as if we’d known each other for years. It felt like a fraternity reunion.
One thing I said to the group while I was there is that you cannot manufacture chemistry. But when you put yourself in situations and circumstances, in environments with truly like-minded people who are brought together by individuals who each one of us know and love and trust, while we may not know the others invited, there is already a common bond. The guard is easily taken down.
That’s how connection works in midlife. You don’t force it. You don’t network your way into it. You show up. You do the thing. You keep showing up again.
And everyone at this table was different. There were finance guys, there were tech guys, there were retired military colonels, there were speakers, there were doctors. Some guys were super into their wine, with vast collections and discerning palates. And there were others, like me who had a ceremonial sip of the Dom Pérignon P3 and 2017 Petrus (because when else am I ever going to get this opportunity!) the rest of the time, we don’t drink.
And it was all okay.
Midlife isn’t about becoming the same. It’s about becoming more yourself and being around people who respect that. No pressure. No posturing. No pretending.
The Decision Point Most Guys Miss
At the end of the weekend, I was supposed to fly back home from San Francisco, but I thought about the importance of experiences over things, and the values we all discussed that weekend as men.
And I decided to do something a bit different. Something inconvenient, yet important.
I switched my flight from San Francisco to Los Angeles so that I could drive the coastline and meet my son for dinner and so that we could fly home together the next morning, as he was scheduled to come home for spring break.
That’s the decision point most guys miss. We default to the easier option. The more efficient route. The plan as written. But midlife is where you earn the right to choose differently, to choose what actually matters.
It’s about being intentional with your time. It’s about scheduling the life you say you want. It’s about staying prepared, physically, mentally, emotionally, so that when the opportunity shows up, you don’t have to get ready. You’re already ready.
As I got to LA and I got the chance to hug my son, I knew I made the right decision.
And just that short period of time, to be with him for a few hours, and then to fly home together, sitting next to each other…
That was the perfect end to a perfect experience.
And a reminder.
This is the stuff.
Not someday. Not when things slow down. Not when everything is perfect.
This. Right now.
The trip you plan. The call you make. The workout you don’t skip. The dinner you don’t rush. The extra hour you give to the people who matter most.
You don’t need Napa.
You need intention. Commitment. A calendar. The willingness to go first.
And the understanding that these aren’t extras.
These are the fun things.
And they’re the ones that actually make your life feel like yours.
In Health,
Greg Scheinman
Founder, Midlife Male
Husband. Father. Entrepreneur. Coach.
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