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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 each had this experience. Independently. Years apart. For a long time, success came relatively easily. Not without effort, but the formula worked. Do the things, get the results. Climb the ladder, reach the next rung. Then it stopped working. And here's what we both realized: That stumble was the wake-up call. When success flows, you don't question the path. Why would you? It's working. The metrics say you're winning. The people around you confirm you're doing great. But when it stops working, you're forced to look up and ask: Wait. Is this even what I want? We may not have questioned any of it if things had kept going well. That's the strange gift hidden in the stumble. It creates space for a question that success had been drowning out: Is this what I actually want? Or just what I've proven I can do? Those are very different things. And most high achievers never confront the difference until the stumble makes them. If you're in a season where things aren't flowing the way they used to, where the formula isn't working, where the confidence feels shakier...maybe that's not a problem to fix. Maybe it's an invitation to ask the questions you've been too successful to ask. What would you be doing if achievement wasn't the answer? Who would you be if the ladder disappeared? The stumble isn't the failure. The stumble is the opening. What's been your experience with the stumble? And how have you been navigating it? Hit reply. Share your thoughts. I read every message. This week, sit with this: What question have you been too successful to ask? |
You built everything you were supposed to build. And you're questioning everything. Quietly. It's not burnout. It's not weakness. It's the slow realization that somewhere along the way, you stopped living your life and started managing it. You're not alone in this. I spent 25 years chasing achievement before I saw it clearly. Every Tuesday, I write about what I found. The patterns. The permission to want something different. The occasional uncomfortable truth. No optimization hacks. No hustle. Just honest exploration from someone a few steps ahead on the same path.
Hey Reader, I’ve noticed there’s one person who’s come up in the last few newsletters that I haven’t named yet: My mentor, Mike. Over the past 15 years, we’ve worked together on countless projects, navigated some tricky situations, and had a lot of honest conversations with each other. Reflecting on my years of working with Mike, I wanted to spend this week exploring what it means to be a good mentor. A lot of us might have been the mentee over the course of our careers, but might not have a...
Hey Reader, Happy Tuesday, friends. About ten years ago, a pretty senior partner asked me to lead something for him. I don’t remember exactly what it was but I remember that as he was explaining things to me, there was a growing sense that I wasn’t the right person for this project. On top of that, my mentor had previously pointed out that I was taking on too much work. Leading one more project would only lead to even more of me stretching myself thin. The advice almost everyone gives for...
Hey Reader, Happy Tuesday, friends. Think of someone you've had to deliver difficult news to. Someone whose reaction you couldn't quite predict. Maybe it's a senior stakeholder, or someone on your team. Either way, you know them well enough to know how they receive things can vary depending on the day. Before that conversation, you probably spent more time than usual thinking about how to frame things. Choosing your words carefully. Picking the right time of day. Maybe even running through a...