Macleans
Earlier this year, I was in the plush boardroom of the wealth-management division of a major Canadian bank, on a floor high above the branch where everyday transactions take place. The investment manager handling my account wasn’t happy. The strategy I’d recommended, she explained, could result in me paying quite a bit more money to the CRA. “That’s okay,” I responded. “I’m comfortable paying more in taxes.” She laughed nervously. “Well, that is the first time I have ever heard that.”
I’m rich. At 30, I sold my small Canadian technology company Dabble DB—an early online-database tool—to Twitter, and my family moved to San Francisco. For the next decade, I worked in senior technical roles at Silicon Valley startups, sometimes in person but mostly remotely from Galiano Island in B.C. I retired at 40 with enough wealth to do pretty much anything I wanted for the rest of my life. When I confided my financial status to a good friend from high school, she looked puzzled. “I’m sure you’re good at what you do,” she said, “but why would they pay you that much? It’s not like you’re a basketball star.” The truth is, I got lucky.
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