Hard won. Freely shared.
The things I wish someone had told me—about the climb, the summit, and everything that happens when you stop long enough to look around.
I’m Not Angry
Most high performers are very good at not being angry. That's precisely the problem.
How Narrow is the Summit?
This is where most conversations about habits stop short — and where the real leverage lives.
The habits that actually move the needle are rarely dramatic. They are almost offensively small. Replacing the nightly glass of wine with a twenty-minute walk. Showing up to the gym because it's Tuesday — not because you feel like it, not because the weather is cooperating, not because everything else is in order. Because it's Tuesday and that's what you do. Researchers call this implementation intention — the if-then structure that removes the decision from the behavior entirely. If it's Tuesday, I train. If I feel the urge to decompress with alcohol, I go outside instead. The decision has already been made. All that remains is execution.
Rich Isn’t Wealthy
Success is not predictable. But the probability of it is influenceable. And understanding the difference between those two things is one of the most clarifying shifts a high achiever can make.
The Hall of Mirrors
There's an old idea—more folklore than science, it turns out—that long-married couples begin to look alike. The theory goes that years of unconsciously mirroring each other's facial expressions gradually reshape their features. Recent research has largely debunked it, but I've always found the underlying intuition worth holding onto. Not the part about faces. The part about what prolonged closeness actually does to how you see yourself.
Marriage is a hall of mirrors. Not the funhouse kind, though it can feel that way—the kind that show you angles of yourself you can't access alone. Some of those reflections are flattering. Some are accurate in ways you'd rather not confront. And some are distortions, shaped less by who you actually are than by what you've each carried into the room. Knowing which is which—that's the work. And most of us are not nearly as good at it as we think.
My New Identity
At 48, shortly after finishing a half Ironman in the top 20% of my age group, I learned something that stopped me cold: I was in terrible shape.
I didn't see it coming. Fifteen years of endurance sports—ocean swims, duathlons, two full IRONMAN triathlons, thousands of miles logged pedaling and pounding pavement. I looked like an athlete. I felt like one. I performed like one (though in one narrow lane). And I was certain that was enough.
It wasn't.
The Wheel That Rolls
For most of my adult life I measured myself with a single number. Net worth. Revenue. Ranking. It didn't matter which—what mattered was that there was always a scoreboard, and I always knew where I stood on it. That kind of clarity feels like direction. It isn't. It's just a very convincing substitute.
After I left Wall Street I sat down with a mentor who gave me a deceptively simple assignment. Draw a wheel. Eight spokes—money, body, work, mind, love, play, community, and spirit. Extend each spoke from the hub based on how fulfilled you actually feel in that domain. If you're genuinely satisfied, the spoke reaches the rim. If you're not, it doesn't. Then look at what you've drawn and ask yourself honestly: is this wheel rolling?
Mine wasn't rolling. It wasn't close.
The Work Beneath the Work
For years, I thought growth meant learning new skills, building better systems, chasing bigger goals. Forward motion felt like the answer to everything. If something was uncomfortable, you worked through it. If something was unresolved, you outran it. I was very good at both, which meant I was also very good at accumulating unfinished emotional business while telling myself I was too busy to deal with it right now.
Strong Before Smart
You cannot think clearly if your body is breaking down beneath you. You cannot make sound decisions under chronic sleep deprivation, or lead with any real presence when you're running on cortisol and caffeine and whatever's left of last quarter's momentum. Strength, stamina, and sleep are not the rewards of a successful life. They are the operating system that makes one possible. And, most importantly, sustainable.
Climbing with the Wrong Map
Most of us only stop to question our direction when we feel lost. That's the cruel irony of ambition. While we're moving—while the calendar is full and the credentials are accumulating and the years are compounding—we mistake investment for direction. We push harder, move faster, tell ourselves we've come too far to turn around now. Until one day we look up, catch our breath, and realize we've been climbing the wrong mountain entirely. All that effort. All that sacrifice. And we're nowhere near where we actually wanted to go.
What keeps most high achievers stuck on the wrong mountain isn't ignorance—it's accounting. The more we've invested in a particular path, the more psychologically costly it becomes to question it. Economists and behavioral scientists call this the sunk cost fallacy: our deeply irrational tendency to continue down a road not because it's leading somewhere worth going, but because we've already spent so much getting this far. The years of climbing. The relationships built around a particular identity. The version of yourself you've been performing for so long it no longer feels like performance. None of that investment changes whether the mountain ahead of you is the right one. But it powerfully distorts your ability to see clearly—and almost guarantees you'll keep climbing long past the point where honest assessment would tell you to stop.
The First (and Only) Time I Got Lost on a Mountain
There's a well-documented phenomenon in psychology called overconfidence bias—our near-universal tendency to overestimate the accuracy of our own knowledge and judgment. The more experienced we become in one domain, the more we unconsciously assume that expertise travels—that the skills and instincts that made us successful in one arena will translate cleanly to the next mountain we decide to climb.
They don't. Not automatically. Not without a map.
By that point I had been operating exactly like this for a decade in my professional life—scaling a single career mountain with the same blind certainty my doctor friend and I brought to Mount Silverheels. Moving fast. Trusting my gut. Mistaking hustle for navigation. And here's the part that's hardest to admit: I wasn't even sure I was on the right mountain. I was just good at climbing.
There's a seductive comfort in forward motion—in the burn of effort, in feeling busy, in the belief that you're gaining elevation. It quiets the deeper question, the one you don't want to ask while you're mid-stride: Is this actually where I want to go?