I just got back from Miami Beach from our first Midlife Male Excellent Adventure.
This is about the single biggest takeaway from the weekend: that confidence comes from doing.
What struck me most is how much value there is in sticking to the basics and doing them well.
Having fun, enjoyable experiences in midlife doesn’t have to be complicated. It doesn’t have to be over analyzed or over scheduled or over done.
You just have to do simple things really, really well:
A great workout on the beach. One instructor. One mat. One kettlebell. The sun and sand and ocean to look at. Simple, not easy. Excellent.
A great meal. High class restaurant. Family style. Terrific location. Solid company. Again, Simple…This was easy and excellent.
When you fill your days with more of that, your confidence rises naturally.
Everything else flows from there.
Quality, not complexity
The real conversations that occur amongst the truly likeminded; not the “likeminded” buzzword that gets thrown around too often and has lost its meaning. These things don’t have to be complicated or expensive. They just have to be intentional.
Quality food. Quality health. Quality experiences. Quality people.
That’s what made Miami so powerful.
We didn’t start with long-winded introductions or forced icebreakers. Instead, guys connected in the Ubers on the way over, across the dinner table, through small conversations. The next morning we trained together, on the beach, sweating it out, pushing ourselves, bonding through movement.
By the time we sat down for breakfast, you could feel the shift. Guards were down. Confidence was up. Guys looked around the table and thought, “I belong here. I can hang with these men. These are good guys.” That sense of belonging didn’t come from words. It came from action.
It helped that everyone there was interesting and curious. We had a hedge fund guy, an author, a speaker, a renowned chef who rowed across the Atlantic Ocean. Every conversation mattered because nobody was a liability. Everyone brought something to the table.
That energy is contagious; you can’t help but rise to the level of the room.
That’s the lesson: confidence doesn’t come from sidelines or speculation. It comes from living. From showing up. From the reps, the meals, the conversations, the experiences. From doing.
And every time I do something, no matter how it goes, I feel my confidence grow.
Confidence doesn’t come from listening to someone try to teach you to be confident. I’ve sat through those speeches, workshops and masterminds.
It doesn’t come from reading countless books on the various ways to develop confidence. I’ve read them and have piles of them that publishers now send me to review.
It doesn’t come from consuming as much content as possible from those who appear galactically confident. I’ve unfollowed too many to count.
Real confidence comes from you, and only you doing the thing. That’s it. There are no other hacks.
It comes from putting yourself out there. From taking action. From wanting to do something and then going out and doing it.
Action builds momentum. Momentum creates motivation. Motivation fuels more activity. But at the root of it all, confidence is developed through action.
Building the “Excellent Adventure”
That’s how this past weekend came about. I had an idea for an Excellent Adventure Weekend that I wanted to create.
So I wrote down exactly what that weekend looked like. The things I enjoy doing that fill my tank. The types of guys I wanted there. The food I wanted to eat. The workouts I wanted to do. Even the clothes I wanted to wear.
And then; three months later – it happened.
Not by osmosis.
Not by hoping.
Not by “manifesting.”
But by actually putting the pieces together one-by-one.
Instead of trying to plan the entire weekend at once, I started with individual questions and built it brick by brick.
The men who showed up
Then there were the guys.
Who did I want to attract and attend? Men 40-60. Accomplished. Six-F guys; interested in family, fitness, finance, food, fashion, and fun. Coaching clients. Readers of the Midlife Male. Friends. Relationships I value.
I reached out and said: This is what I’m doing. I’d love for you to join me.
And 15 incredible guys committed.
That’s important. That’s not lost on me. They did something too. They took time away from busy lives, made a leap, and invested in themselves.
They didn’t just say “someday.” They booked it, showed up, and did the thing they’ve always said they wanted to do, but rarely do.
That’s how confidence is developed.
As the weekend unfolded, surrounded by men who added value, challenged me, and belonged there – I felt myself elevate. The energy fed off itself.
And when I got home, the momentum carried. I went through my “re-entry” protocol: shaved my head, put on a face mask, got a manicure and pedicure, hit my sauna, jumped in my cold plunge. All the things that fill me up, that make me feel good, that keep me confident.
And then I opened my computer to write this column – my battle cry to men out there.
Why this work matters
This is why I coach men, and work with a coach myself.
This is why I serve others and seek to improve myself.
This is why we invest in ourselves and in each other.
So we can live happier. Healthier. Wealthier. Stronger. And have more fun.
That’s the thing.
This is the thing.
Jon (our editor-in-chief) and I have a running joke about keeping things simple.
We always say, “The thing is the thing”.
It doesn’t have to be more than that.
Because confidence isn’t found on the sidelines.
It’s found in the arena. Whatever your arena may be.
And here’s the good news: it’s never too late to and you’re never too old to get back in the game.
Confidence comes from doing.
So the real question is, what are you going to do?
_________________________________
Invitation to men in midlife
Ready to do the thing?
If you’re a guy in midlife who’s tired of sitting on the sidelines and ready to build real momentum, join Greg at MEA this April.
He’s co-leading Master the Middle: A Midlife Reset for Men with MEA CEO Derek Gehl and Faculty-in-Residence Ben Katt. It’s a 5-day immersion in Baja built around the exact framework he used to reset his own life.
You’ll ruck at sunrise, surf, cold plunge, and do the work that builds confidence through action. You’ll leave with your personalized Midlife Action Plan and a community of men who get it.