The Lie Beneath Your HustleHow your hustle became your hiding place.You’re addicted to tactics because strategy requires something far scarier: honesty about what you actually want. I know because I was a tactics junkie too. Had my morning routine locked by 5:47am. Read every negotiation book, and got so good at managing up my boss thought I was magic. I got the promotion. Senior executive. The title I’d chased for years. Six months later I was in the hospital. My perfectly optimized life had collapsed. Turns out I’d mastered answering the wrong questions, and it nearly killed me. You’re Drowning in Other People’s AnswersOpen your browser history. Go ahead; I’ll wait. It’s likely a graveyard of desperate searches:
But every how-to article is someone else telling you what game to play. You lap it up because tactics feel like progress. You think you’re doing something. But you’re NOT progressing. Instead, you’re procrastinating on the real work. You’re hiding. You can wake up at 3am to journal about cold showers all you want, but you’ll still be dead inside by lunch. Upgrade Your QuestionsTactics are comfortable. Strategy is confrontational. Let me show you the difference between the garbage questions you’re asking yourself and the real ones you’re avoiding. Garbage: “What’s the best productivity system?” Real: “Why do I need military discipline just to survive my own life?” Garbage: “How do I get promoted faster?” Real: “Why am I begging for validation from people I don’t respect?” Garbage: “How do I find work-life balance?” Real: “Why did I design a life where work is prison and everything else is parole?” You get the point. The quality of your life depends on the quality of your questions. Keep asking garbage questions, and you’ll stay stuck in the life you claim not to want. Why “Why” Scares YouThe deep, soul-work questions don’t have tidy answers you can implement by Monday. There’s no framework for admitting you’ve been cosplaying someone else’s life. No app fixes an identity built on other people’s expectations. When you ask “how,” you stay busy. When you ask “why,” you get real. Reality tastes bitter.
I spent years perfecting tactics for a strategy I’d never questioned. World-class at climbing a ladder that was leaning against the wrong wall. The Day I Stopped Playing DeadAfter the hospital, after recovery, after the humiliation of optimizing myself into a medical emergency, I did something radical - and I encourage you to do the same. I stopped asking “how” and started asking “why.”
The answers sucked. They showed I’d been living like a well-trained corporate zombie, confusing motion with progress and exhaustion with importance. But once I got honest about the “why,” the “how” became irrelevant.
The tactics are simple when you quit playing the wrong game. It turns out you don’t need more hacks when you stop living a life that requires constant self-bullying to maintain. Time to Choose Your DiscomfortYou’ve got two options.
Why are you working so hard to build a life you need to escape from? Don’t Google it. Don’t journal it. Don’t turn it into another project. Just sit with how much that question pisses you off. That anger, that discomfort? That’s your soul trying to wake up. Stay comfortable with your tactical band-aids, or get uncomfortable with the truth. Your call. If that question made you want to punch something, congratulations. You’re ready for real work. But most of you will close this tab and wonder “how to find your passion.” Prove me wrong; close your browser. Go stare at your life for 60 seconds. Then decide if you’re done bullshitting yourself. Quotation I’ve Been Pondering“A life built on motion is easy. A life built on meaning is much harder, but well worth the effort.” — Tim Parkins Journal Prompt“Where in my life am I choosing motion over meaning. And why?”
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I help successful yet unsatisfied professionals craft a working life that works for them. Every Sunday night I send a newsletter with actionable tips, strategies, and reflections designed to help you work and live a better, more fulfilling life.
When You Stop Trusting the Path When the work still matters - but the way you’re chasing it doesn’t. When the destination is clear, but the path is uncertain. I spent at least four hours this week optimizing my home network. It wasn’t broken. It wasn’t even slow. But there I was, buying new mesh nodes, running speed tests, rearranging cables, and screwing with network settings like it was mission-critical work. I also browsed Black Friday sales for things I don’t need and don’t even really...
Driving Blind: Why Your Career Feels Like a Snow Squall When you can't see where you're going, someone else's taillights become your plan. Last week I hit a wall of snow on the highway. It was one of those classic Ontario squalls where visibility drops to fifty feet and every driver becomes a white-knuckled philosopher questioning their life choices. In that moment, I wasn’t “making decisions.” I was reacting. Slow down. Follow the taillights. Hope nothing suddenly materializes out of the...
The Subtraction Myth: Why Less Isn’t Always More Meaning isn't found in what you remove, but what you build. You can’t subtract your way to a positive — only to zero. You’ve read Essentialism. Deep Work. Maybe even Four Thousand Weeks if you were feeling existential. You tried their tactics. Said no to meetings, batched your emails, and protected your calendar like it’s a castle under siege. You subtracted the bullshit, set boundaries, focused on “what matters most.” And yet - you’re still...