Added On: Friday, November 21, 2008

How They Got Their Big Break

Maureen Farrell and Melanie Lindner 11.13.08, 3:45 PM ET

Here's the hard truth about big breaks: They don't just happen; people make them happen--through hard work, networking, courage, passion and pain.

And as much as modern culture has glorified the notion of the "big break" (with American Idol its ultimate homage), lasting success has a lot less to do with singular, transcendent moments than it does with incremental progress and unflagging grit.

"People do get lucky breaks, but usually they have already made a decision about what they want to do and have pursued it with tenacity," says Paul Bernard, a Manhattan-based executive career management coach.

Sometimes vision and tenacity don't kick in right away, as Jon Stewart knows. Voted "Best Sense of Humor" by his high school graduating class in Lawrenceville, N.J., Jonathan Stuart Leibowitz logged time after college as a construction worker, busboy, assistant high-school soccer coach and puppeteer for disabled children before mustering the confidence to move to New York. There he made his stand-up debut at The Bitter End--the same comedy club where Woody Allen began his career. After a few movie stints, Stewart went on to fake-news stardom as host of Comedy Central's The Daily Show.

Big breaks are also about spinning loss into opportunity. Barbara Corcoran, founder of The Corcoran Group, New York City's largest residential real estate agency, owes her rise to a painful event: breaking up with her boyfriend. Back in 1973, he lent her $1,000 to start a real estate agency and took a 51% stake. Seven years later, he ran off with the company's secretary, ultimately giving her full control of the company.

"Thank God, or I never would have been in business on my own and learned I could stand on my own two feet," Corcoran told last year. She did a lot better than that: In 2001 Corcoran sold the business for $71 million and is now a real estate commentator for CNBC.

Late-night funnyman David Letterman broke into show business with a flop. After a string of guest appearances on second-tier sitcoms and game shows, Letterman landed a hosting gig for a comedy pilot called The Riddlers. The series was a bust, but Letterman got noticed by the higher-ups at The Tonight Show with Johnny Carson. He soon became a regular guest, and the rest, as they say, is history.

Real estate mogul Larry Silverstein certainly didn't wait for his big break--in fact, he built his empire brick by brick. He began his career in the 1950s by converting a Manhattan industrial shack into an office building. It took myriad deals over five decades to get where Silverstein, 77, is today.

"I didn't have a clue what I was doing in the beginning," he told Forbes. "You have to stick with it." He'll need every bit of that conviction to pull off his finale--rebuilding the World Trade Center site, into which he sunk $800 million the summer before the Sept. 11, 2001, terrorist attacks.

No matter what, when lady luck comes knocking, you'd better be ready to pounce. Just ask rising actor Michael C. Hall. It took three years after graduating from New York University's Tisch School, but Hall got his break when he met director Sam Mendes at a musical workshop.

At the time, Mendes was directing Cabaret on Broadway. When the actor playing the "emcee" stepped down, Mendes called Hall to try out for the role. By that evening, Hall was practicing with the choreographer, and within days he was on Broadway. Hall has since landed cherry gigs on Dexter, airing on Showtime, and HBO's Six Feet Under.

The good news about big breaks is the best way to get them is by doing what you love. Case in point: Steven Spielberg. The legendary director has been making movies--and money--since he was a kid, when he charged a 25-cent admission fee per screening. While attending California State University in Long Beach, Spielberg made his first short film, the 24-minute Amblin’. After Sidney Sheinberg, then vice president of production for Universal's TV arm saw the film, he signed Spielberg to a long-term directorial contract. And we're all pretty happy about that.

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