How 9 Extremely Successful Businesspeople Handled Setbacks

Don't let a curveball throw you for a loop. Find out how Richard Branson, Craig Newmark, Rachel Zoe and other leaders met challenges head on.
April 24, 2014

No matter how smart, experienced or hard-working you are, you'll eventually come face-to-face with a setback or two in your career.

Sometimes the curveballs force you to prove everyone wrong, as Wall Street powerhouse Sallie Krawcheck did when no one—not even her longtime mentor—believed in her abilities. Other times it involves losing everything you hold dear, including your company, your marriage and your home, as oil magnate T. Boone Pickens faced in his late 60s. Or maybe you have to make heart-wrenching decisions in order to move forward: Billionaire Richard Branson chose to sell his record label in order to keep another company afloat—and cried in the streets of London after his decision.

The fact of the matter is, when that curveball is coming right at you, you've only got one option: Swing at it for all it's worth. Even if you miss, the experience of trying will stay with you forever.

And that's exactly what these major leaguers did. As LinkedIn's recent "Career Curveballs” blog series illustrates, each of them successfully moved on from their setbacks, taking powerful lessons along with them.

Below are our picks for the nine most moving—and informative—lessons from the "Career Curveball" series.

Richard Branson, Founder of Virgin Group


Richard Branson, Founder of Virgin Group


Branson was running a successful record label with such talent as The Rolling Stones, Culture Club and The Sex Pistols when he decided to get into the aviation industry. When Branson told his business partner, the partner shouted, "For God’s sake! You’re crazy. Come off it."

But to be a real entrepreneur, Branson believes you always have to be looking forward and not get too comfortable with what's working. So he stuck to his aviation vision, though not without some hardship along the way. At one point, in order to give the airline "the financial muscle to compete," as Branson puts it, he was forced to sell Virgin Records, a company he'd built from the ground up.

"It was the right decision but an incredibly tough curveball moment," Branson says. "I found myself running down Ladbroke Grove in London with tears streaming down my face and a $1 billion [check] in my pocket."

Today, the former high school dropout is the eighth richest person in the U.K., according to Forbes' list of the world's billionaires

Naomi Simson, Founder of RedBalloon

In the early 1990s, Simson started a new job as the loyalty club program marketing manager at a prestigious iconic Australian aviation brand she was proud to be working for. Little did she know that within months, she'd be miserable in her new job.

Soon after starting there, Simson was asked to help launch the first points-based frequency program to ever exist in Australia. Now doing two jobs for the same salary, Simson worked hard to launch the program, but her superiors didn't understand the time and effort it would take to get things off the ground. After months of handling a double workload, Simson finally got up the courage to ask for a raise. The general manager's response shocked her: “Who do you think you are to come into my office and ask for a pay rise?” he replied. “How do I know what value you add to this business?”

"I left his office trying to hold back the tears, feeling not only diminished but also angry and hurt," Simson says. "I was indignant: How could he not know my contribution?" A direct manager was able to negotiate a $5-per-week pay increase for Simson, which was "as insulting as the lack of recognition," she says, and Simson turned in her resignation letter the next day.

Not long after leaving, Simson was asked to join Apple, then, eventually, she started her own company, RedBalloon, which creates employee recognition and incentive programs. 

Sallie Krawcheck, Owner of 85 Broads


Sallie Krawcheck, Owner of 85 Broads


Before her career in finance, Krawcheck had been a journalist at Institutional Investor, so when she started working at research firm Sanford C. Bernstein, some of her colleagues didn't have much faith in her abilities as a financial analyst. Nonetheless, Krawcheck moved up the ranks to become director of research with the help and encouragement of her mentor.

Despite her experience, when her mentor left the company immediately after her promotion, Krawcheck experienced "a public nightmare vote of no-confidence," as she puts it.

"I will never forget the first research meeting after [my mentor] left and the humiliation I felt. My boss took me aside to ask me if I still felt able to do the job," she says. "The real answer, of course, was no; the answer I gave was yes, but I remember as I was saying it, my intestines felt like they were falling into my feet."

Without the day-to-day guidance of her mentor, Krawcheck was forced to think differently about the analysis side of the business and make decisions based on her own judgment. She did the job no one else thought she could do.

"I really don’t know what strategy we would have pursued at Bernstein if my mentor had stayed. But I do know that it is hard to conceive of and effect significant strategic change when a business is operating well," Krawcheck says. "I would have felt much more constrained, certainly seeking his counsel and most likely seeking his approval. There was a freedom in being forced to stand on my own two feet, even if it involved getting knocked off of them first."

Stan McChrystal, Co-Founder of McChrystal Group LLC

McChrystal had been a soldier for 38 years when his career came to an abrupt end after the publication of a Rolling Stone article in 2010. The former commander of all U.S. and NATO forces in Afghanistan was asked to meet in person with President Obama. At that meeting, he turned in his resignation letter, and the president accepted.

On that day, McChrystal had no idea what he was going to do with the rest of his life.

"... My very identity as a soldier came to an abrupt end. I’d been soldiering as long as I’d been shaving. Suddenly I’d been told I could no longer soldier, and it felt as though no one really cared if I ever shaved again," McChrystal says. "I’d caught a curveball directly on the chin; I wanted to find a corner of the dugout, away from TV cameras, to rub my head and maybe sniffle a bit."

But McChrystal didn't want to go on feeling like a victim. He refused to write a tell-all that would have labeled him as a victim—and would have probably ended up as an instant bestseller.

"I faced some immediate and profound questions: What am I in the world if not a soldier? Who am I to those around me if not a General Officer?" he asks. "This was not a query for consultants or confidants. I needed to step back up to the plate and prepare to read the next pitch."

His next move was to focus on people, a skill the Army had taught him in all those years as a commanding officer. "Like leaders in many walks of life, my business has been to serve with, and for, others," he says. "By focusing on this simple truth, and allowing it to guide my decisions through a difficult time, this curveball ultimately opened as many doors as it closed. From starting a [consulting] company to teaching at Yale, the past few years have been full of incredible experiences shared, most importantly, with true and lifelong friends."

T. Boone Pickens, Founder of BP Capital and TBP Investments Management


T. Boone Pickens, Founder of BP Capital and TBP Investments Management


In 1996, four decades after founding it, Pickens lost his company, Mesa Petroleum. At the same time, his 24-year marriage was ending, he was forced to move out of his home into a hotel, and his best friends were killed in a car accident. Pickens was 68 years old and was eventually diagnosed with clinical depression. With the odds stacked against him, he could have called it quits, but he didn't.

Instead, he decided to focus on improving himself mentally and physically. When things started getting better, Pickens realized "it wasn’t the world against Boone; it was Boone against Boone," he explains.

"Once I put the past behind me, my mind cleared, my focus returned, and I was on my way," Pickens says. That's when he founded a new company, BP Capital, which has become a leading commodities fund.

"Things will get better if you hang in there and believe in yourself," Pickens believes. "The attributes and skills that made you successful in the first place don’t disappear. I had been struggling at the plate for five years or so, but I was entering a period when nearly every swing would result in the ball going out of the park."

Glenn Kelman, CEO of Redfin

When Kelman was 28 years old, he was in charge of product management for Plumtree Software, a company co-founded, but he had problems with the board. On the day he was asked to meet with the chairman, Kelman knew he was going to get fired. At the end of their 45-second chat, Kelman told the chairman he wouldn't leave and promised to change—he even cried. He was given just one more chance, and Kelman went back to work with a new mindset.

"All the things I imagined my successor doing, I did," Kelman says. "The company went public. The CEO and I became good friends. I was able to look on my eight years there as a success, not a failure."

Since his career setback, Kelman has never stopped feeling lucky—even in his role today as CEO of Redfin. "I've sometimes wondered if Bill Gates would still be burning to save Microsoft today if only he had earlier been fired from it, as Steve Jobs was fired from Apple," he writes. "Feeling lucky also fills you with love. Most CEOs walk around the office like we own the place, without realizing that the place itself isn't worth owning: A business's value comes from the people who walk out the door every night, who have to decide each morning whether to walk back in. One of the simplest things you can do as a leader is honor their choice and appreciate their work."

Craig Newmark, Founder of Craigslist


 Craig Newmark, Founder of Craigslist


Newmark has always been very candid about his difficulties and lack of managerial skills. "Any career success I enjoy has been by virtue of getting downsized," he says. "For me, that means either laid off or otherwise made an offer I couldn't refuse, like an internal transfer, sometimes with a big demotion."

At IBM in Detroit, Newmark helped sell a lot of computer systems, but he was a poor team player and often lost his patience. He once lost it in front of customers and "created an instant perception of not playing well with others."

Around this time, Newmark began working at Charles Schwab, which moved him to San Francisco, where he started a mailing list about arts and tech events in the city. As the mailing list grew, he took on more and more employees, who, in 2000, effectively told him he wasn't a good manager. His solution? To demote himself from CEO to customer service rep.

"By that point," he says, "I'd internalized the big lesson: that the only way I learned and moved ahead was the right kind of trauma."

Inge Geerdens, Founder and CEO of CVWarehouse

Early in her career, Geerdens wasn't as lucky as Kelman was— she was actually fired and forced to leave the company she'd been working for. But still she managed to come out on top.

In 1995, a young and eager Geerdens was working for a recruiting firm that didn't believe it was necessary to invest in technologies. When Geerdens suggested the importance of the Internet to her boss, she received a cold shoulder.

"I suppose my disappointment showed when I left her office. I got sacked just a few days later," Geerdens says. "I guess juniors are simply too young to have a vision on the future of the company. Therefore, I was trouble."

This lack of faith in her ideas lit a fire under Geerdens, however, and she decided then that she would never work for another boss. She soon started her own tech-savvy recruiting firm, and within five years, the brand was so strong, she was able to sell it.

As for her former boss? Her company went bankrupt five years later.

Rachel Zoe, CEO of Rachel Zoe Inc.


 Rachel Zoe, CEO of Rachel Zoe Inc.


Fashion icon Zoe knows how to turn any dilemma into an opportunity by focusing on the good and faking it until you make it. Her advice? Never tackle problems on your own; instead, turn to the people you trust the most. For Zoe, those people have been her mentors and close family members.

But don't turn to these people unprepared. If you find out that things didn't turn out the way you thought they would, Zoe advises, you should always have a list of possible solutions ready before you present the problem to others. As a designer, Zoe says the prototypes of her designs haven't always come out as she expected. But instead of starting from scratch, she and her team work to find a middle ground that will please both her and her customers.

And if you find yourself with an opportunity you're not quite ready for, resist the urge to panic, Zoe says, and just dive in. This happened to Zoe when she received her first big styling job to dress Jennifer Garner for the Emmy Awards in 2003. Instead of passing on the job because she was too nervous and inexperienced, she trusted her gut and accepted the job. Eleven years later, Zoe is one of the top fashion stylists in the world.

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Photos: Getty Images