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...
8 days ago • 1 min read
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...
15 days ago • 1 min read
There's a strange paradox about January. Every ad, every influencer, every gym promo tells us this is the time to sprint. New goals. New habits. New you. Attack the year before it attacks you. But look outside. At least in the northern hemisphere, it's the middle of winter. The days are short. The light is thin. Every living thing is conserving energy. Except us. We're supposed to be "hitting the ground running." See the problem? The "new year, new me" energy isn't motivation. It's pressure...
22 days ago • 1 min read
Here's a question most people never get asked: What would be enough? Not "what do you want?" You've answered that a thousand times. Not "what are your goals?" You have spreadsheets for that. Enough. The number, the title, the lifestyle where you could exhale and say: this is what I was building toward. I'm here. If you're like most high achievers, that question just short-circuited something. The most successful people I know have never defined enough. They can tell you exactly what they're...
29 days ago • 2 min read
Right now, millions of people are doing the same thing. They’re opening fresh notebooks. Downloading goal-setting templates. Writing “2026” at the top of the page with something that feels like hope. By February, most of those pages will be forgotten. Not because they lacked discipline. Not because they didn’t try hard enough. But because the goals were never theirs to begin with. Here’s what most goal-setting advice gets wrong: it focuses entirely on the HOW. How to set SMART goals. How to...
about 1 month ago • 2 min read
First: we named the Success Trap. Second: we talked about why it's not your fault. Now: the five patterns. Most people recognize at least two. The Success Trap isn't one thing. It shows up differently depending on how you got caught in it. Over years of working with senior executives, I've seen five distinct patterns emerge. Each one is a different flavor of the same core experience: building exactly what you were supposed to build, and feeling like a stranger in it. See which ones land for...
about 1 month ago • 2 min read
Last time, we named it: the Success Trap. That quiet dissonance between what you've built and what you actually feel. Today: why it's not your fault. Let's get something out of the way. That feeling you have? The one where you've done everything right and something still feels off? You're not crazy. You're not ungrateful. You're not broken. You're responding exactly the way a human responds when they've been following someone else's map for a very long time. Here's what's actually happening....
about 2 months ago • 2 min read
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...
about 2 months ago • 2 min read