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Corporate Graduation™

Trade corporate success for entrepreneurial ownership. Every Saturday, get one memo — to help you navigate the complex shift from the default path to an authentic life powered by a premium business, with bold thinking and grounded conviction.

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Futureproof yourself

#009 | Read Online By Matt Doan · August 9, 2025 · 3 min read Futureproof Yourself There’s a shift happening right now It’s quiet for some. Undeniably loud for others. Jobs are flattening. Titles are losing meaning. AI is rewriting the rules before you even learn them. And the people who will thrive in the years ahead? They won’t be the ones with the flashiest credentials. They won’t be the ones frantically trying to keep pace with the latest tech. They’ll be the ones with the most courage....

#008 | Read Online By Matt Doan · August 2, 2025 · 2 min read The Energy Tax It was always Sunday afternoon that hurt the most. That was the time I’d start packing. Laptop, chargers, button-downs, just enough ties to keep the image sharp. Early Monday morning, I’d be back at the airport—bleary-eyed, stomach tight, apologizing to my family again. “I’ll be gone three nights this time. Maybe four.” It became routine. Predictable. A successful consultant living the dream. Except it was eating me...

#007 | Read Online By Matt Doan · July 26, 2025 · 3 min read The Harmonized Life We just got back from an epic family trip across Europe. Probably the most enjoyable vacation I’ve ever had. To start, we flew business class—not because of corporate status or points, but because we built a business that earns it. We swam in the crystal-clear waters off the Croatian coast. Biked through Amsterdam parks, wind in our hair, with the little dude in tow. Rode public trams like locals. Ascended 400...

#006 | Read Online By Matt Doan · July 19, 2025 · 3 min read It Gets Late Fast You think you have time. But the signs are everywhere. Some loud. Some silent. You don’t recognize the worn face in the mirror. You wake up tired, even on weekends. Great jobs used to be everywhere, but suddenly you’re “too experienced.” Ageism doesn’t shout; it creeps in quietly, until one day you’re no longer the clear choice—you’re the backup plan. You once fantasized about traveling the world with your family...

#005 | Read Online By Matt Doan · July 12, 2025 · 3 min read The Onlyness Edge “Matt, you’re not technical enough.” That sentence didn’t just sting—it split something open inside me. I was the head of a global strategy team. I could see complex systems from high orbit, translate ambiguity into clarity, navigate board-level decisions with fluency. But apparently, that wasn’t enough. They wanted me to blend in. To become more like everyone else. To chase technical certifications and stack...

#004 | Read Online By Matt Doan · July 5, 2025 · 3 min read The Happiness Decision 7:30 AM. James sat in his home office, second cup of coffee in hand. His eyes glazed over. He stared blankly at the next slide deck on his screen—a presentation he had to critique and send back to his team. It wasn’t the task itself. It was the endless repetition. The constant urgency. The sinking feeling that none of it truly mattered. The relentless corporate carnival played on: a flood of pings and dings...

#003 | Read Online By Matt Doan · June 28, 2025 · 3 min read Let Fear Light the Way “You need to leave this marriage.” Those words landed like a thunderclap in my therapist’s office. I remember sitting there, stunned, a thousand thoughts crashing through my mind. Three kids—how could I possibly walk away and miss the majority of their childhood? The weight of that decision felt crushing. I never imagined I’d be the person contemplating this, yet here I was, grappling with a truth I couldn’t...

#002 | Read Online By Matt Doan · June 21, 2025 · 3 min read The Two Selves Gap 2,000 people. Spotlights, panels, applause. It was a massive cybersecurity conference in Dallas. I was dressed sharp. Confident. Mic’d up on stage, saying all the right things. To anyone watching, I was “on.” Articulate. Poised. Respected. But inside? I felt numb. I had delivered those lines a hundred times before. And in that moment, they felt dead—like I was cosplaying a version of myself that once made sense,...

#001 | Read Online By Matt Doan · June 14, 2025 · 3 min read The Forgotten Phase of Leaving Corporate Most people assume that leaving corporate is a moment. A decision. A resignation letter. A dramatic pivot. A number in their bank account. But the truth? It’s rarely a clean break. It’s a phase. A process. A slow unwinding of one identity… and a gradual construction of another. I call it the Gray Space. You’re not fully in, not fully out. You still show up to meetings. You still collect the...

Read this (+ previous posts) online Issue #190 Read time: 3 minutes We’ve been trained to believe freedom comes decades from now. But that’s only true if you keep playing by traditional rules. Here’s how to accelerate what actually matters — starting now. The Secret You want freedom. But not the kind they sell you on Instagram. You want to wake up energized — clear on what you’re building and why it matters. You want to be present with your family without guilt or distraction. You want work...