The 10 Greatest Career Moves of All Time

Publication: BestLife

By Isaac Guzman

Sometimes the only thing separating a VP from a CEO is one savvy move.
From life-altering to Lilliputian, pesky decisions swarm us daily, like no-see-ums in a Tallahassee swamp. Most of us just slap at them with the haphazard petulance of a zebra's tail. But our heroes know better. Especially when it comes to bailing out a stalled career or emerging stronger from a nightmarish day at the office. Here are the men to meditate on when you reach your next occupational hazard, for they are the ones who made the modern world's greatest career moves.
10. David Bowie
The challenge: Born David Jones, he had been playing saxophone in an R&B outfit called Davey Jones & the Lower Third. But in 1966, another Davy Jones turned up... and he was in the big leagues as lead singer of the Monkees.
Move: Changed last name to Bowie, traded sax for guitar, dabbled with Buddhism and avant-garde theater. In 1969, scored a major (Tom) smash with "Space Oddity."
Lesson: Sometimes, the very things that have gotten you where you are can be the same things that will prevent you from going to the next level. "Adapt to change, keep experimenting, and don't let small things prevent you from building an extraordinary career," says executive coach Rachelle J. Canter, PhD, author of Make the Right Career Move.
9. Carl Bernstein
The challenge: After six years at the Washington Post, Bernstein was stuck covering a journalistic backwater, Virginia politics, in 1972.
Move: Helped out on the first day of Watergate break-in coverage. As Bob Woodward moved forward with the reporting, Bernstein got back on the story by rewriting Woodward's copy without being asked.
Lesson: "A great idea often starts with one person and is refined by another," says Karen Danziger, managing partner at the Howard-Sloan-Koller Group, in New York City. "I'm not suggesting you ride on coattails, but if you see something you're passionate about, get on the bus. It's better to be a passenger on the bus that's going where you want to go than the driver of the bus that's heading for a dead end."
8. Charles Bukowski
The challenge: A Skid Row regular who bedded fellow barflies and brawled like a sailor, Bukowski was celebrated for his writings about life lived at the bottom of a bottle. After decades of debauch, the plot was wearing thin. The acclaim wouldn't stop his lifestyle from killing him.
Move: Relocated to a working-class suburb in San Pedro, California. Didn't sober up completely (it would take a round of chemotherapy a decade later to do that), but managed to keep his life together and a BMW in the garage. Now a literary lion, he befriended Sean Penn, Madonna, and Norman Mailer. Married-and stayed married to-his second wife, Linda, and enjoyed his success with only a fraction of the earlier chaos.
Lesson: "Life is a series of choices," says Canter, "and you can always make a different choice today."
7. Ralph Lauren
The challenge: Having moved from tie salesman to $10-million-a-year fashion phenom, Lauren (whose family changed its name from Lifschitz when he was 16) was good at designing clothes, but manufacturing costs were out of control, and Polo was going broke in the early '70s.
Move: Farmed out production and marketing on every-thing but his men's line; plowed his life savings into the plan. Within a decade, he was doing $1 billion of business a year.
Lesson: Assessing your strengths with steely objectivity and then concentrating your efforts "is one of the least applied concepts in corporate America," says Bill Pullen, a career coach in Washington, D.C. "My motto is 'Do what you do best and find people to help with the rest.'"
6. Matt Groening
The challenge: Everybody in L.A. was reading Groening's weekly comic Life in Hell, which featured a cast of existential rabbits and a pair of gay twins named Jeff and Akbar. But in Hollywood, the money he was making seemed like a pittance.
Move: Producer James L. Brooks asked him to pitch animated shorts for The Tracey Ullman Show, but Groening didn't want to give up the rights to his franchise. So on the spot, Groening sketched out five scrappy characters based on him and his family. He sold Brooks on the Simpsons instead of the rabbits.
Lesson: Just because the idea came to you in two minutes doesn't mean it's not genius. "Intuition is our sixth sense and the most underused in the human experience, especially in the professional and business world," says Pullen.
5. Frank Sinatra
The challenge: In the early 1950s, Sinatra was a has-been crooner, being forced by producer Mitch Miller to sing-and woof-novelty tunes such as "Mama Will Bark." In 1952, Columbia Records dumped its former golden boy.
Move: Sinatra decided it was time to grow up out of his bobby-sox image. He took a challenging role in From Here to Eternity and won an Oscar. He parlayed that into a deal with Capitol Records, demanding that he be paired with adventurous arrangers such as Nelson Riddle, and recorded dark brooding records such as "Only the Lonely." It's the greatest comeback in pop-culture history.
Lesson: The Chairman of the Board has taught us so much that we won't even try to sum up his vast reserves of wisdom. We'll just note that he reveled in the spoils of his move. Years later, he reportedly ran into Miller in a Vegas hotel. Miller approached, his hand extended, and Sinatra blew him off: "F--k you! Keep walking!"
4. King Camp Gillette
The challenge: As a worker drone in a bottle-stopper outfit, young Gillette was looking for a way to echo the success of his employer. He, too, wanted to profit from America's rapid move toward disposability.
Move: When his straight razor went dull, Gillette had his great vision. Instead of charging a fortune for high-quality straight razors, he'd make cheap blades that could be thrown out. He sold the shave, not just the razor, inventing a new business model.
Lesson: "He looked for the most meaning-ful lesson in his past experience: disposability," says Jordan Ciambrone, a certified wellness coach in New York City. "You have to put in the time and do the research, and then the connections are made and the revelations come."
3. Eric Schmidt
The challenge: A Silicon Valley programming prodigy, Schmidt was a chief architect of Java at Sun Microsystems and later rose to CEO of Novell. But by the end of the '90s, Novell was being left in the dust by Microsoft. When the company was bought out, Schmidt headed to Google.
Move: Fortysomething Schmidt let his then-girlfriend drag him to the Burning Man Festival. He hated it and left early. When he later interviewed to be CEO of Google, founders Sergey Brin and Larry Page hired him... because he was the only candidate who had been to the desert free-for-all. Thanks to one hot, dusty date, he's now a billionaire.
Lesson: "You have to be willing to take the risk to present something that makes you unique and different," says Joel Garfinkle, a Bay Area executive coach. "If you stand out, you create opportunities for yourself."
2. Justin Timberlake
The challenge: In 2002, 'NSync's sales were slipping, manager Lou Pearlman was taking most of the group's money, and Timberlake's dim-but-doable girlfriend Britney Spears was said to be cheating.
Move: Dumped all three, scored a triple-platinum hit with "Justified," and later hooked up with both Cameron Diaz and Jessica Biel.
Lesson: "The company you keep can hinder or help your potential for success," says Tory Johnson, CEO of Women for Hire, a New York-based recruitment services firm. "Align yourself with people who lift you up: those who are smarter, savvier, and wiser than you are."
The savviest career move of all time... Kenneth Cole
The challenge: In the mid-'80s, Cole designed his first line of shoes. To attract buyers, he planned a stunt: Peddle them from a tractor trailer parked outside a footwear trade show in New York City's crowded Midtown. But the city grants that kind of parking permit only to filmmakers.
Move: Got new letterhead, changing his company's name from Kenneth Cole Inc. to Kenneth Cole Productions, and told the city he was going to shoot a documentary called The Birth of a Shoe Company. Secured a permit and sold 40,000 pairs in two and a half days.
Lesson: "There are often loopholes that yield creative solutions to problems," says Danziger. "Finding the creative way to have a win-win is what brings respect and admiration from your peers."