"Last Thanksgiving, my dad and I were sitting on his back porch, and he was telling me about a new supplier he'd found for his shop. He was genuinely excited. Not startup-pitch excited. Not Series-A excited. Just... quietly, deeply engaged in a problem he'd been solving variations of for three decades. And something shifted in me that I'm still processing months later."
"I looked at him - 67 years old, same business, same town, same routines - and for the first time in my life, I didn't feel an ounce of pity. I felt envy. That's a weird thing to admit when you've spent your entire adult life building the opposite. I sold my first company at 27. A mobile app for small business appointment management. It wasn't a massive exit, but it was enough to make me feel like I'd outgrown my father's world."
"And it took a failed startup, deep debt, a relationship that fell apart because I was emotionally unavailable, and about fifteen years of therapy to understand why. The story I told myself for twenty years In my twenties, I had a narrative about my dad that felt airtight. He was a good man who played it safe. He had talent - the guy can fix anything, talk to anyone, solve logistical problems that would make most people's heads spin - but he never "went for it.""
Last Thanksgiving the narrator watched his 67-year-old father become quietly excited about a new supplier, and felt envy rather than pity. The narrator had sold a company at 27 and believed ambition required constant expansion, using the father's steady business as a cautionary contrast. After a failed startup, deep debt, a broken relationship, and fifteen years of therapy, the narrator reevaluated that belief. Ambition proved tied to identity rather than a binary trait, and the father's skill, consistency, and contentment represented long-term mastery rather than stagnation. The narrator admits previous judgments were spectacularly wrong.
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