I got the text. “Skyline Traverse. 18th. You in?”.
That’s all it said. It was from Bart Foster. That’s all I needed to know.
I checked my calendar. I’d have to fly straight to Boulder from Palm Beach and then from Boulder to Atlanta.
So what?
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I told Kate that I was invited by Bart to join 40 executives, speakers, thought leaders, and entrepreneurs willing to wake up at 5 AM, push themselves, and show up fully. 20 miles. Five Peaks. 10 hours.
This was no ordinary group. These were exceptional men (and a few exceptional women), and I felt a wave of gratitude wash over me that I was being included.
So many guys who’ve won by the time they’re in midlife go around living their lives like they’ve lost. I call them 3M guys: miserable, midlife millionaires.
Well, guess what? There’s a whole other bunch of guys out there who’ve won and they’re living like it. And when you hang with them, you’re like, holy shit, “this is how you do it!” And I got to experience it firsthand.
First we lined up in a parking lot: two lines, facing each other.
Bart and his partner Bobby Africa (one of the best names ever), put us through an ice breaker exercise. If you have kids, take a step forward. That was pretty much everyone. If you have two kids, three, four, five… There were only two guys with five kids. Have you written a book? A few of us had. Started a company? Almost all. Sold a company? Almost all. Closed a company? Most. Run a marathon? Many. Ironman? Quite a few. Ultra? I think only one.
There were more questions, these are just the ones I remember as I soak my sore body in an epsom salt bath and write.
With the ice broken, we carpooled to the trailhead. Dark, cold, and with no idea of what to expect, we began. We were told that over the course of the day, we’d pair off and be given prompts to talk about. I’m not usually into this type of thing, but I was all in on this. I also think it was distracting me from the altitude and steepness of the hike itself. We were told to keep our conversations confidential and to not share the stories of others. They’re for them to share, not for us to repeat. I like that very much.
At each peak, Bart asked the group if anyone wanted to share a story. It was only a few years ago that I’d have tried to hide and avoid being called on. Today I promise myself that when asked to speak, my hand is the first to go up. The physical is easy for me. This is not. And that’s why I do it.
So, on top of an epic mountain, at almost 10,000 feet, I shared some of my story, and about how, after almost 53 years on this planet, I finally feel like a man who’s very much on top of his own mountain, and yet still looking for the next peak. I wouldn’t even have attempted that peak if not for two guys on the hike, Tim, an Olympic triathlete, and Adam, a world-renowned rock climber, who simply said “come on”, and I followed them.
With each mile, and each ascent, I learned something. I did a lot of listening. I tried to do less talking. However, the interesting thing about being around really smart people is that they try to do more listening than talking as well and ask really great questions, so there’s like this little “jockeying for position” game going on constantly where you’re looking for an opening to get your questions asked, and answered.
At one point, Bart had me walking with him for around thirty minutes, before I finally said “I’m going to get some questions for you in here too!”
Here’s what I didn’t hear. Not one guy on that mountain said, “I wish I was in the boardroom longer.” “I wish I actually sold this company for twice as much.” “I wish I built it 10x as big.”
Every one of them was like, “Can’t believe I was somehow smart enough to pack my bags and move to Boulder, and realize that enough is enough.” There were guys who talked about no longer missing their kids’ birthdays. Another guy was telling a story where he realized he had worked seven Christmas days in a row. Everyone came back to figuring out what success looks like for them.
My favorite part of challenges like these is never who “comes in first.” It’s who finishes last. That guy is special. Because he’s the one who’s so outside his comfort zone, so uncomfortable and was so scared to say yes to doing this, and yet is still out here, getting it done that everyone rallies around him. It was my favorite part when all but one of us were at the last summit, and then finally, the last man standing arrived. Everyone cheered. The guards were down. The moment was complete. And it was awesome. 
Until it wasn’t… for me. I realized that I never hike downhill, ha! In all the events I do, I hike up and gondola down, so this time my knees were freakin’ killing me! That part sucked. You needed to know that. It can’t be all rainbows and unicorns…
Bart told me that these moments were powerful and that “some of the best conversations happen when we slow down, step outside, and give our full attention to the people beside us.”
This day was a reminder of how powerful that can be.
And he’s right.
In Health,
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Greg Scheinman
Founder, Midlife Male
52. Husband. Father. Entrepreneur. Coach.
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