The Decade's 10 Best Career Moves

Who made proactive moves necessary for success in this volatile decade? Who shot themselves in the foot? And what can we learn from them both? The Daily Beast picks the winners and losers, career-wise.

Gary Gershoff / Getty Images

Gary Gershoff / Getty Images

Millard “Mickey” Drexler

Current position: CEO, J. Crew

Signature move: Success is the best revenge

At Gap Inc., Drexler turned a sleepy denim retailer into an arbiter of casual style and forever changed the way Americans dressed. Then, on May 22, 2002, after 19 years with the company, the last seven as CEO, it all came to a screeching halt. Frustrated by a 29-month sales slump, founder Don Fisher fired The Merchant Prince. “I was devastated,” Drexler told The Daily Beast. “I cried.”

Redemption, it turns out, was just across the shopping mall. J. Crew came calling, and Drexler jumped at the chance to give the down-on-its-luck preppy clothier a new sheen. How did he know it was the right move? “My vision of the future was so compatible with what I thought J. Crew could be,” he says. Seven years later, Gap has foundered, while J. Crew has prospered. Drexler has long since moved past the anger he felt on the day he was fired and even made peace with Fisher, who died in September. “People who have bounced back often say it’s better the second time around,” Drexler says. “In my case, that’s true.”

Mario Tama / Getty Images

Hillary Rodham Clinton

Current Position: Secretary of State

Signature Move: Professional divorce

Just a decade ago, Clinton was viewed by many as the pathetic wife, a brilliant woman who placed her own career ambitions on hold to further her philandering husband‘s interests. Unlike other former first ladies, however, Clinton was not about to spend the rest of her life at charity lunches or tea parties. Her 2000 senatorial run launched Clinton into an orbit separate and distinct from that of her charismatic husband's—one of the most brilliant career moves in modern political history.

Of course, that was just the beginning. Her bid to become the first female president cemented her stature, and today, as secretary of State, her role in American politics currently eclipses her husband‘s. “She was willing to work in the trenches to revamp her identity,” says Pamela Mitchell, a career coach and author of the soon-to-be released Ten Laws of Career Reinvention: Essential Survival Skills for Any Economy. True, Clinton has made mistakes. (The botched health-care overhaul and her vote to support the war in Iraq are two that come to mind.) But like her or hate her, it’s hard not to respect her.

Michael Loccisano / Getty Images

Susan Lyne

Current Position: CEO, Gilt Group

Signature Move: Get back in the saddle

You name it in the media world, Lyne has done it. She went from editing Premiere magazine to running all of prime-time programming for ABC Entertainment. Then, in spring 2004, just weeks before she was to unveil a fall lineup that included future hits Desperate Housewives and Lost, she was shown the door. “For 48 hours, I thought the world had ended,” Lyne told The Daily Beast. “Then I realized what an incredible opportunity I had.”

She took the summer off and did some soul-searching. She also dipped her toe back into the media word, joining the board of Martha Stewart Living Omnimedia. When Stewart shipped out to Alderson Federal Prison Camp that September, she became CEO. Over the next four years, she returned the company to profitability and then moved on. Next stop: Gilt Group, an online sample sale that attracts the young and trendy with discounts on the latest fashions. “I tend to get bored when things are going well,” Lyne says. “I love the excitement of a turnaround or a startup. That allows me to take a different kind of risk than a lot of people are comfortable with.”

Scott Wintrow / Getty Images

Tom Freston

Current Position: King of all media

Signature Move: Patience as a virtue

He built MTV and Nickelodeon into powerhouse cable networks, and then in 2006, Viacom Chief Sumner Redstone abruptly gave him the ax, reportedly for passing on buying MySpace—a move that now looks prescient. Thirteen days after he was fired, he boarded a plane with his wife, her mother, and his brother and began a tour of 30 countries, including Singapore, Cambodia, China, and Afghanistan. Oprah Winfrey finally tracked him down in Burma and convinced him to consult for her OWN Network. U2 frontman Bono also pressed him into service helping revamp the singer’s humanitarian organizations. Then Richard Holbrooke recruited him as a trustee of the Asia Society. He’s now also working with Moby Media, an Afghan-based television company.

With a full plate, Freston says getting canned turned out to be a blessing in disguise. “The tendency is to go right back and do a variant of the same thing,” he says. But if you use the experience “as a punctuation mark, it becomes an opportunity to craft a new chapter in your life.”

Sipa via AP Photo

Tom Ford

Current Position: Director, The Single Man

Signature Move: Channel your creativity

His designs helped turned Gucci into a provocative symbol of luxury and excess as well as a highly profitable fashion brand. The good times stopped rolling when Ford and business partner Domenico De Sole clashed with Gucci’s new owners, PPR, over creative control. Ford resigned in 2004, leaving fashionistas everywhere in despair. The months that followed were difficult. “I didn’t know who I was,” Ford told Tina Brown in a recent Daily Beast interview. “I didn’t know what I had to say. I didn’t have a way to say it. It was very painful.” What he learned after a short hiatus was that “I never want to retire until the day I drop dead.” In 2007, Ford launched a men’s wear brand that sells custom-made suits and $75 socks, as well as eyewear and fragrances. His directorial debut, The Single Man starring Colin Firth, has garnered several award nominations, including three Golden Globes. And ladies, the wait is over. Ford recently confirmed that he will begin designing women’s clothing again, perhaps as soon as next fall.

Sipa via AP Photo

Susan Boyle

Current Position: Recording artist

Signature Move: Bravery in the face of humiliation

For most of her 48 years, Boyle lived a remarkably unremarkable life. She grew up singing in her parish church, trying like so many other hopefuls to break into the big time. She once used all her savings to record a CD that she sent to record companies to no avail. It was her mother who urged her to audition for Britain’s Got Talent. The two were devoted fans of the show. But Boyle resisted, believing she was too old. Then, after her mother died in 2007, Boyle, who lived with her cat Pebbles and publicly declared that she’s never been kissed, was so grief-stricken that she stopped singing for two years.

When she heard the show was holding auditions in Glasgow, near her home in Blackburn, she put her inhibitions aside and took the plunge as a tribute to her mother. Boyle grabbed the world spotlight with her stunning rendition of I Dreamed a Dream. It was one of the most viewed videos of the Internet age. The rest, as they say, is history. “She was willing to step outside her comfort zone,” Mitchell says. “And she had someone who believed in her more than she believed in herself.”

Bill Pugliano / Getty Images

Sarah Palin

Current Position: Bestselling author

Signature Move: Plays by her own rules

When she was plucked from obscurity as John McCain’s running mate in the 2008 presidential election, the Alaska governor got a rare chance to make her mark on the national stage. But one flub after another (the Katie Couric interview, her wardrobe malfunction) left Palin open to ridicule and helped unhinge McCain’s bid. After the election, her political future seemingly put on ice, Palin headed back to Alaska.

But she didn’t stay there for long. She resigned as governor—a move that was mocked, but has freed her up to dominate the Republican political discussion and actively promote one of decade’s biggest publishing successes, Going Rogue: An American Life. “She didn’t just do what was expected of her and she struck while the iron was hot,” Mitchell says. With her uncanny knack for coining quotable phrases (“death panel” anyone?) she continues to have a growing impact on the political debate.

Peter Kramer / AP Photo

Jennifer Hudson

Current Position: Actress, singer

Signature Move: Small ego, big comeback

First, the American Idol finalist was voted off the show. Then Simon Cowell, who had the first option on her recording rights, passed. Hudson went back to singing the local club circuit. Her big break had come and gone and that was that.

Or was it? Hearing about an open casting call for the movie Dreamgirls, she attended an open casting call just like any other anonymous actress. She won the part of Effie White, an Oscar for Best Supporting Actress, and the cover of Vogue magazine. “She didn’t see the setback as the end of the road,“ Mitchell says. “She was willing to go back and start again.” Despite a personal tragedy (her mother, brother, and nephew were murdered in 2008), Hudson continues to perform, at the Super Bowl, the Grammy Awards, and a fundraiser with President Obama.

Paul Sakuma / AP Photo

Jamie Dimon

Current Position: CEO, J.P. Morgan Chase

Signature Move: Don’t drink the Kool-Aid

It was a partnership made in banking heaven. For 16 years, beginning in 1982, Jamie Dimon and Sandy Weill worked pinstripe-to-pinstripe building what would become the financial behemoth Citicorp. Then it was over. Weill fired his longtime protégé in 1998, and for two years Dimon kept a low profile.

He re-emerged as Bank One CEO. And when J.P. Morgan Chase acquired Bank One, he became first president and then CEO of the giant Wall Street firm. While his competitors—led by Citigroup—gorged on exotic financial instruments that would turn toxic, Dimon played it (relatively) safe, leaving his firm in a (relatively) strong position after the meltdown, and himself as the rare hero in a saga filled with villains.

Despite this, Dimon, in a rare show of self doubt, told the Harvard Business School graduating class of 2009 that he hesitates to give advice, “because it sounds like I did” everything right, when “I did not.” When you fail, he told students, it's OK to get depressed and cry. But eventually, you have to “get over it.” Success, he said, isn’t only based on the things you do right, but how well you survive the things that go wrong.

Stephen Lovekin / Getty Images

Robert Downey Jr.

Current Position: Sherlock Holmes

Signature Move: Married well

It’s a comeback made for the big screen. Promising young actor is laid low by drug addiction. Repeated attempts at rehab fall flat and the actor’s behavior turns increasingly bizarre—he was once arrested for driving naked on Sunset Boulevard—until he is all but un-hireable. An attempted comeback with a role on the TV show Ally McBeal backfires. Then, in 2002, starring opposite Halle Berry in Gothika, he meets executive producer Susan Levine. With her help, he gets clean and gets hitched. (The two married in 2005.) Salvation came in the form of a comic-book hero. Downey landed the title role in the blockbuster hit Iron Man, putting him back on the map. Next up: the starring role in Sherlock Holmes.