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Welcome to Second Summit Brief. Every Tuesday morning, a quiet moment before the noise. For leaders who've succeeded by every measure, and are quietly wondering if there's more. Let's start with the question you might be afraid to ask out loud: What if you succeeded brilliantly...at someone else's dream? You hit the numbers. Got the title. Built the thing everyone said you should build. And somewhere along the way, a quiet thought started showing up uninvited: Is this it? Not a crisis. Not burnout. Something harder to name. A gap between what your LinkedIn profile says and what your nervous system knows. You're not falling apart. You're succeeding. That's what makes this so disorienting. I call it the Success Trap. It's what happens when you climb with discipline, talent, and relentless effort to reach a summit that was never actually yours. Someone else drew the map. Parents. Professors. The culture that rewards titles and compensation and corner offices. You followed the trail because it was well-marked and the view was supposed to be worth it. And now you're standing at the top, looking around, thinking: I worked really hard to get here. But I'm not sure this is my summit. Here's what I've learned: this is way more common than anyone admits. On the drive home. In the shower. At 2am when the house is quiet. A lot of people are feeling this. Senior leaders with decades of success. Founders who built exactly what they set out to build. Partners at firms they once dreamed of joining. Externally crushing it. Internally questioning everything. But nobody talks about it. Because how do you say "I have everything I'm supposed to want, and something still feels off" without sounding ungrateful? Without sounding broken? So it stays quiet. And in that silence, people assume they're the only one. You're not the only one. In my work with senior executives, I've noticed when the real conversation starts. It's usually after the strategy talk, when the door is closed. It sounds like: "Can I tell you something I haven't told anyone?" The Success Trap isn't a character flaw. It's not a failure of gratitude or discipline or perspective. There are real reasons this happens. The way our brains are wired: chasing the next hit of achievement because it kept our ancestors alive. The way society defines success: a narrow path that looks like progress but might just be someone else's definition of winning. The way families pass down expectations: sometimes spoken, sometimes just absorbed. These forces are powerful. And mostly invisible. This week ahead: notice when something lands. A meeting that drains you. A conversation that lights you up. Your body is keeping score, even when your mind hasn't caught up. What about this resonates? What are you struggling with? Hit reply. Share your thoughts. I read every message. Next up: We'll go deeper on this. Why this isn't your fault, and why the dissonance you're feeling might actually be the sanest response to an insane setup. |
Second Summit Brief is a weekly letter for high-achieving leaders who’ve realized the summit they climbed isn’t the one they want to stay on. Each edition blends reflection and strategy to help you see the patterns keeping you stuck and find the clarity, courage, and integration that define your own second summit.
There's a question most high achievers avoid at all costs: Who are you without the title? Not what you do. Not what you've built. Not what's on your LinkedIn. You. The person underneath the credentials. If that question makes you uncomfortable, you're not alone. For most of us, identity and achievement have been fused together for so long that we can't see where one ends and the other begins. We became the role. The performer. The one who delivers. And it worked. That identity got us...
There's a version of the Success Trap that doesn't look like burnout or emptiness. It looks like things just...not working the way they used to. The formula that always delivered starts to sputter. The wins get harder. The confidence that came from a long track record starts to crack. Not catastrophically. Not publicly. But enough that you notice. I was talking with Kathy Wu Brady recently (follow her on LinkedIn), and we stumbled onto something that stopped us both mid-conversation. We'd...
You're allowed to outgrow a place that once felt right. Even if everyone says you're thriving. This is one of the hardest forms of misalignment to recognize. There's no obvious villain. No toxic boss, no unreasonable workload, no clear reason to leave. You deliver great results. You get along with the people around you. You've built your success over years. And still...something feels off. When something's obviously wrong, it's clear you need to make a change. But it's much harder to see...