He went from working in a factory to being rich enough to retire at 32—but 3 decades later, this millionaire still works and takes public transport

Bill Holland achieved what many people spend their entire careers chasing: by age 32, he had made enough money to retire for good. But over three decades later, the now-67-year-old still hasn’t hung up his hat.

The former CEO of CI Financial, one of Canada’s largest investment management firms, didn’t take a conventional path to the top. Despite graduating from Toronto’s York University, Holland drifted through a string of self-described “crappy jobs,” like delivering 7Up, working in a factory, and serving as a doorman at a Toronto bar before finding his footing in finance.

At 27, he landed a customer service representative position at Mackenzie Financial Corp.—a demanding job that required fielding roughly 120 customer calls a day, according to a recent profile in Canadian business publication Financial Post.

“People would complain about how hard the job was, but unless you are doing something that involv...