Why the Best Success Stories Often Begin With Failure

One writer’s unexpected bout of unemployment inspired him to catalogue the misadventures of those who came before him

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Illustration by Lisel Ashlock

Long before the iPhone made him the god of gadgets, Steve Jobs launched his tech career by hacking land lines to make free long-distance calls.

Bob Dylan’s band, the Golden Chords, lost a high-school talent competition to a tap dancing act.

Behind every success story is an embarrassing first effort, a stumble, a setback or a radical change of direction. It’s these first clumsy steps on the road to fame and fortune that fascinate writer Seth Fiegerman, who edits the blog OpeningLines.org, a collection of case studies on the origins of famous careers.

“When you see someone who’s very successful, you almost imagine that it was a foregone conclusion, that they’re a genius, that they were destined for great things,” says Fiegerman, who began the blog in 2009, after an early setback in his own career. “I think the big takeaway is failure and setbacks, far from being uncommon, are in many ways essential.”

After Fiegerman, now 26, graduated from New York University in 2008, he landed a coveted first job as a research editor at Playboy magazine. But he had worked there for just half a year when management announced that most of the staff would soon be laid off.

As unemployment loomed, Fiegerman felt adrift. He began to explore the Playboy archives, discovering a trove of interviews with celebrities ranging from Marlon Brando to Malcolm X. Many of these successful people shared tales of their less promising early days, and Fiegerman quickly became obsessed with these origin stories.

“It kind of paired well with this feeling that I had of, ‘Oh my God, what do I do?’” Fiegerman says. “And I found solace, in some ways, reading about the obstacles that famous figures had to overcome.”

He began devouring biographies and soliciting interviews with writers and musicians he admired, using the blog to document the fits and starts that began the careers of the famous and the infamous. Success, he learned, was less a matter of innate talent and more the product of perseverance, a willingness to stumble and stand up again and again.

“You kind of assume that great geniuses [are] like Mozart,” Fiegerman says. But few successful people were child prodigies, and prodigies don’t necessarily find success. “Most people don’t stick to it.”

Author Jennifer Egan stuck with it. She told Fiegerman that her first novel was so bad even her mother hated it. But Egan kept writing, and her writing got better—in 2011, she won a Pulitzer Prize for her novel about growing old in the digital age, A Visit From the Goon Squad.

Knowing about a hero’s early flops and foibles might disillusion some fans, but Fiegerman finds comfort in rough beginnings. “The only thing that would have disappointed me is if I’d researched all these guys and women and found out that they got it right on the first try, because, OK, I did not,” Fiegerman says with a laugh.

Like his subjects, Fieger­man found that his own early setback wasn’t permanent. He landed a new job in journalism, and today he works at the tech news website Mashable, covering, appropriately enough, start-up businesses. While he has less time for the blog, he hopes his collection of origin stories will help other young people realize it’s OK to fail.

“I hope some of them benefit from it,” he says. “But if nothing else, I feel like I benefited from it a little bit.”

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