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How to Re-Engage Your Confidence in Middle Age

Plus: The Simple Strategy We Used to Plan Our Miami Excellent Adventure

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Why Confidence Comes From Doing

I just got back from Miami Beach from our first Midlife Male Excellent Adventure.

This isn’t a full recap of that weekend; that’s coming. I promise.  

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 does not 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.

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. And 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. 

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 brick by brick:

Where should we train? I called my friend Marc at Anatomy Gym in Miami. “Can you help us put together some beach workouts?” He said yes; and orchestrated everything from that point forward.

Where should we stay? Marc connected me with the One Hotel Miami Beach and its GM, who graciously welcomed us.

I wanted to capture the event. Within days, I had three recommended videographers from three different friends. 

I wanted stone crabs and fried chicken at Joe’s Stone Crab. I called Joe’s, coordinated with Aida, and suddenly we had a dinner for 15 with custom Midlife Male menus.

I wanted pizza at Lucali on Saturday night. Called, booked, confirmed. They treated us like kings.

What about a Midlife Male Sunrise Ruck? So I called GORUCK and pitched the idea. They sent us all backpacks and 20lb plates and customized patches to commemorate and place on every pack.

Yes, these were all things “I” wanted to do. That’s the point. 

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 got closer, I felt it building. Pulling my bag from the closet, choosing outfits that make me feel like me.

Friday night at Joe’s in my favorite Levi’s vintage jeans, Alex Crane black linen tee and Chuck Taylors

Saturday workouts in my black Arc’teryx shorts and my Midlife Male shirt Harper designed.

Casual nights in Buck Mason pants, tan Alex Mill tee, Birkenstocks

My Panerai watch. My Apple Ultra 3. The four pairs of glasses I pack in my Moscot travel case. A mix of iconic, timeless pieces, high and low, that feel authentic.

Confidence comes from looking and feeling like yourself.

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.

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?

In health, 

Greg 

PS: Need help figuring out what you’re going to do and how you’re going to do it? Reach out and reply to this email. I’ve helped hundreds of midlife men develop their Midlife Action Plan (MAP) and get back what matters most to them.  

And if all of the above sounds like an amazing time to you, and you’d like to get advance information on our next Excellent Adventure (this one sold out fast), use this form here.

Take the PLUNGE

At 52, I take my recovery seriously. In fact, I invest more time, energy, and money into recovery now than I do my workouts. That’s why I’m so excited about the new Plunge All-In.

I was one of the first 100 people to own an original Plunge, and I recently upgraded to the new All-In model; and let me tell you, it’s worth everything.

It’s quieter. Longer. Sleeker. Fully digital. I can control it from my phone. It gets colder, faster. The maintenance is easier. The access to the filter and chiller is simple. And on top of all that, it looks great in my backyard.

I use mine 4–5 days a week, two minutes at a time, keeping the water around 50 degrees. The benefits are undeniable:

  • Improved blood flow

  • Less lactic acid buildup and soreness

  • More energy

  • Better mood and overall health

  • And I sleep like a baby. (I’m more of an evening “plunger”!)

The Plunge All-In has streamlined my recovery, improves my sustainability and longevity and it’s become a cornerstone of my routine.

There’s no way around it, I’m hooked.  Having a PLUNGE helps me feel better, and live happier, and healthier in every way. 

In health,

Midlife Male
52. Husband. Father. Entrepreneur. Coach. Student of the game.
Still walking the walk.

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