Much of Dick Costolo's professional track record is impressive: In June 2007, he sold his company FeedBurner to Google for a reported $100 million. And from 2010 to 2015, Costolo was CEO of Twitter. In 2013, he took the social media company public.
But some of his early career decisions seem to make less sense when you think of his corporate success.
Costolo graduated in 1985 from the University of Michigan with a major in computer science. But he turned down computer programmer job offers to move to Chicago and try to make it in improv. His goal was to appear on NBC's "Saturday Night Live."
He never made it as a professional comedian.
Still, Costolo says his time in Chicago studying improv was extremely valuable.
And that life experience informs his own best advice for young people who are trying to figure out what to do with their lives: Don't do what you are supposed to do, Costolo tells CNBC Make It.
"First of all, there is extraordinary pressure on students to come out of college sort of knowing what they're supposed to do," says Costolo. "I gave the commencement speech at the University Michigan in 2013 and I specifically told them, 'Don't do that — don't do what you think you're supposed to do.'
"Instead, take risks. Take big chances," he says. "The younger you are, the more risks you can take. You've got fewer responsibilities and probably don't have a mortgage or even you know kids or dogs or cats yet."