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Corporate Graduation™

Trade corporate success for entrepreneurial ownership. Every Saturday, receive one essay — 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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Don’t build a job that's worse than your corporate one

#015 | Read Online By Matt Doan · Sep 20, 2025 · 3-min read Freelancer vs. Entrepreneur “Should you find yourself in a chronically leaking boat, energy devoted to changing vessels is likely more productive than energy devoted to patching leaks.” —Warren Buffett You’re finally out of corporate—or getting close. Maybe you jumped. Maybe you were nudged. Maybe you just hit your limit. Now comes the big move: You take your corporate skills and reputation. You repackage it all into your own...

#014 | Read Online By Matt Doan · September 13, 2025 · 3-min read The Comfort Penalty You tell yourself you’ll get going when the time is right. After this quarter. After the next raise. After things “settle down.” Even when you know something’s off—that you’re clearly meant for more. But life isn’t that bad… right? You’re surviving. You're paid well. You’ve got the title. You’re respected. So you wait. Another day. Another week. Another year. That’s the trade most people are making. Quietly....

#013 | Read Online By Matt Doan · September 6, 2025 · 3-min read Breaking the Pattern of Deferred Freedom You keep climbing the ladder. Maybe it’s for status. Maybe for safety. Maybe because it’s all you know. You think: “If I keep going, I’ll eventually earn my freedom.” That logic runs deep. Decades of programming. You assumed promotions would unlock ease. That stock, bonuses, and seniority would finally give you control. But now, something feels horribly off. Or maybe you’ve already...

#012 | Read Online By Matt Doan · August 30, 2025 · 4 min read How to Solve the Whole Corporate Graduation™ Puzzle (Not Just One Piece) “I’ve had a few consulting gigs, but it’s slow going.” “I’m invested in a small real estate portfolio, but we keep hitting dips.” “I put $50K into a franchise, but it’s more draining than my current job.” I hear this all the time. From smart, ambitious people who want out of corporate life—but are stuck. Yes, they’re motivated. They’re not lazy or naive. But...

#011 | Read Online By Matt Doan · August 23, 2025 · 3 min read Make Your Employer Your Investor “It’s 10 AM. I’m at a coffee shop. And I’m done with my workday.” That’s my client, Travis. Director at a multi-billion dollar company. Just two weeks earlier, he was working 12-hour days. Holed up in his home office. Drowning in Teams messages and global pings. A ghost to his family. Burned out and buried. Then, everything changed. He faced the truth. He got strategic. He made his employer his...

#010 | Read Online By Matt Doan · August 16, 2025 · 3 min read The Illusion of Progress You say you want a profound shift in your world. To step beyond the constraints of corporate life. To design your own rhythm. To build a business, brand, and life that finally feels like yours. Yet despite all your intentions, little has changed. You’ve read the books. Listened to the podcasts. Ripped through endless AI chats. You keep gathering inputs, hoping: “Maybe just one more insight… one more...

#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...