👔 The Suit
In 2017, I sat at the 30-person dining table in Masayoshi Son’s $150 million home. All eyes were on me as I pitched a deal to Masa and his team—some of the brightest minds on Wall Street.
When my part was done, I handed things off to a colleague and surveyed the room. Two thoughts hit me in rapid succession:
1) “This is the top.” I’d come a long way from bagging groceries in small-town Texas for $3.35 an hour.
2) “I don’t want to be here.” I was living someone else’s dream, not mine.
That moment of clarity would change the course of my life.
I’d reached the pinnacle of my career only to realize I climbed the wrong mountain. Months later, I hit the reset button, quit a prestigious job, and moved my family to Colorado with no clear plan for the future.
Fast-forward 8 years…
Since that epiphany in Masa’s dining room, I’ve spent over a thousand days outside instead of in an office. I climbed a second mountain—both literally and metaphorically—and the view from this summit is better.
I still work hard—in fact, I recently started a business. But now I work on my terms. My career is just one part of my identity, and not the defining one.
The other guys seated at Masa’s table that day undoubtedly took their careers to great heights. They’re richer than me, but…
Who’s more successful?
That’s not for me to answer, but here’s what I’ve observed in my 30-year pursuit of happiness:
Financial wealth is common. There are a lot of rich guys out there, but very few have threaded the needle, with career success and also…
—Passionate non-work pursuits
—Exceptional health & fitness
—A close, loving family
—Control of their time
—A lasting marriage
The rare breed that achieves success across multiple dimensions—they’re the ones I want to emulate.
👔 The other day, while rummaging around in our basement, I stumbled upon the Armani suit I wore in that meeting with Masa. It was dusty—a relic of a distant world.
Everyone’s path is different—maybe yours involves Armani suits and boardrooms. My point is:
Choose your mountain carefully—because you just might make it to the top.
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