Michael Terry honed his wit while working in finance. Now he’s a full-time comedian.

by Chris Taylor

Michael terry once led a double life. After 12-hour days at his buttoned-down job as an investment banker, he’d slink into the grimy streets of New York City to hit the comedy clubs. His secret life performing stand-up didn’t quite sink to the moral nadir of, say, former New York governor Eliot Spitzer’s. But to people like Terry’s conservative midwestern father, the notion of giving up a well-paid gig raising money for hedge funds in favor of the creative life was just as obscene.

For four years Terry, 37, was able to juggle his corporate and creative halves — until he kept moving up the ladder. “My job was becoming all about office politics, and that just didn’t interest me in the least,” he says. So last summer he opted for his true love full-time, hitting the stage with his sketch-comedy troupe Party Central USA.

It was a bit of luck that allowed Terry to make the jump. As the credit crisis was first revving up, his employer Morgan Stanley was looking to lay people off, so he volunteered to get canned. By raising his hand he got a severance package equal to about three months of salary, which, along with an accumulation of company stock and some savings, could fund a stab at comedy for a couple of years — but only if he cut his budget to the bone. “Part of me is still a numbers dork, so I sat down and budgeted every single line item in my life, right down to my subway pass and pairs of socks.” By slashing his entertainment budget and not eating out he was able to chop incidental expenses from $2,000 a month to a lean $500.

The biggest challenge, says the Wharton grad, was the lack of daily structure. “For 14 years I’d worked in an environment which was as regimented as you could possibly imagine,” Terry says. “Now I could wake up and watch Oprah all day, and nobody would tell me what to do.” He decided to block out 40 to 60 hours a week for writing, editing, or performing and treat that schedule as seriously as if each minute were a personal sit-down with Morgan Stanley’s CEO.

Terry has now notched two commercials and a spot on the satirical news show of the Onion, and has been invited to submit his work to Saturday Night Live. But he warns that anyone opting for a performer’s life should develop the thickest of skins. “ ‘You’re not funny’ is certainly more painful than ‘You’re not making managing director this year.’ ” On the flip side: “The first time I did stand-up, the audience applauded so much after one of my jokes that I had to wait and let it die down before I could continue. Best feeling in the world.”

The Tactics

1. PUT SOME STRUCTURE IN YOUR LIFE: “For a creative person, this is the real challenge,” says Andrew Susskind, a Los Angeles–based life coach. He recommends the Getting Things Done, or GTD, method. “It’s a time-management system developed by consultant Dave Allen (davidco.com) that maximizes stress-free order and productivity. A couple of its key techniques: the 43 Folders method of slotting every task into its daily or weekly place, and the Two-Minute Rule of tackling chores immediately if they can be done in under two minutes. Instead of being overwhelmed by all the things you have to do every day, you record, review, and prioritize them in a very systematic way.”

2. FIND A MENTOR RIGHT AWAY: This is essential if you’re entering a new creative field. “Reach out to your university alumni association or mentoring organizations like SCORE (score.org) to find the right match,” says VocationVacations’ Kurth. “Keep in mind that just because someone has great credentials doesn’t mean they’d be a good mentor. They have to have a passion for the field and truly want to share what they know. You can even take the relationship to the next level by volunteering or working part-time with them.”

Read the rest of Men’s Journal’s Change Your Life package here:

Make your hobby your livelihood

Devote yourself to a cause

Leave it all behind

This article originally appeared in the January 2009 issue of Men’s Journal.