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There's a moment in Alice in Wonderland that I keep thinking about. Alice comes to a fork in the road and asks the Cheshire Cat which way she should go. His answer: "That depends a good deal on where you want to get to." "I don't much care where—" "Then it doesn't matter which way you go." We laugh because it's absurd. Of course it matters which way you go. But here's the thing: most of us are Alice. We're moving fast, working hard, optimizing everything. And we never got clear on where we're actually trying to end up. Then we wonder why we feel like we're walking in circles. The Success Trap isn't about lack of effort. It's about misdirected effort. We walk faster and faster through the forest, collecting achievements like breadcrumbs, and somewhere around year fifteen we look up and think: How did I get here? Is this where I wanted to go? The honest answer, for many of us: we never actually decided. We defaulted. We followed the path that was handed to us. We optimized for speed without questioning direction. And now we're deep in a forest that doesn't feel like ours, wondering if it's too late to choose differently. It's not. But the work isn't moving faster. It's getting clear on where you actually want to go. Not where you should want to go. Not where the world says success lives. Where you want to end up. This doesn't require a ten-year plan. It means asking questions you may have skipped in the rush to achieve. How often are you deciding which way to go, versus letting others decide for you? And what would change if you decided your own path? Hit reply. Share your thoughts. I read every message. This week, sit with this: If you could arrive anywhere five years from now, what would that life actually look like? Not the résumé version. The real one. Where do you live? Who's close to you? What does your time go toward? What have you stopped doing? Don't answer with goals. Answer with details. Notice what comes easily and what feels hard to imagine. Both are data. The Cheshire Cat was right. If you don't know where you're going, any road will take you there. But when you get honest about where you want to end up, even partially, even imperfectly, the path starts to reveal itself. P.S. Having trouble finding YOUR direction? Try out the Before You Climb worksheet. |
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.
Think about who you were ten years ago. Your priorities. Your certainties. The things you thought you’d never change your mind about. The identity you would have described if someone asked. Now think about how much has shifted since then. Not just circumstances. You. The way you see the world. What matters. What doesn’t anymore. If you’re honest, the change is probably significant. Maybe dramatic. And yet. If I asked you how much you expect to change in the next ten years, the answer would...
We've gotten very good at eliminating friction. One-click purchases. Algorithmic playlists. Instant everything. The entire tech economy is built on the premise that friction is the enemy, that smoother is better, that the goal is to remove every obstacle between you and what you want. And for some things, that's genuinely useful. But here's what I've started to notice: The easier something becomes, the less it seems to mean. The song that plays automatically doesn't land the same as the one...
There's a story about a martial arts student who approaches his teacher. "How long will it take me to master this craft?" The teacher considers him. "Ten years." The student nods, then leans forward. "But what if I practice twice as hard? What if I train every day, longer than anyone else? How long then?" The teacher smiles. "Twenty years." Most of us are the student. We believe that more effort solves everything. That if something isn't working, we just need to push harder. Stay later. Grind...