Career

10 People Who Turned Failure Into Massive Success

It can be difficult to imagine the likes of JK Rowling and Bill Gates encountering roadblocks on their way to millions – but they did, and are living proof that just because the going’s tough now, it won’t necessarily be this bumpy in the future. In fact, they credit their failures with making them more determined to succeed. If you’ve had hiccups in your career, this may be the reassurance you need.

From fashion designers and tech-company founders, to journalists and, well, Oprah, these success stories show that everyone stumbles on the road to glory. You may have been fired, accidentally sent a whingey email to your boss instead of your colleague, or are struggling to get your money-making idea off the ground but, as the below winners prove, you can still make it to the top.

Arianna Huffington

You’d think that after having her second book rejected by 36 publishers, Arianna Huffington would have thrown in the towel and declared defeat. This initial failure was in addition to being dropped from hosting duties on a BBC show early on in her career, supporting her ex-husband in a failed bid to become a Republican senator, and her first foray into the world of digital, a website that called for Bill Clinton’s resignation (clearly not a success). Since, she’s had no troubles finding people to read her work, with her internet newsroom, The Huffington Post, getting clicks by millions each month. And her book career? She’s racked up 15 tomes – proving her mother’s adage that “failure is a stepping stone to success”.

Oprah Winfrey

Of all the women in the world, the last person you’d expect the words ‘unfit for television’ to apply to would probably be Oprah Winfrey. But that’s exactly what a producer at a Baltimore TV channel told her before firing her from an evening news reporter job. Far from letting it get her down, she segued into a career as a talk-show host, which saw her giving away cars and gaining a cult following for 25 seasons. Now, she’s worth more than $3 billion, runs a media empire, and is a respected philanthropist.

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Jeff Bezos

You wouldn’t think that the guy who was so successful at selling books online that he’s credited with single-handedly ruining the bookstore industry (only to turn around and open a bookstore) had experienced any failure. But, prior to founding Amazon, Jeff Bezos launched zShops, an online auction site, which crashed and burned. Learning from his errors, Bezos repurposed the idea and started Amazon. He now encourages his staff to take risks – even if there’s every chance they might fail. Indeed, even Amazon has experienced its fair share of disasters – billions of dollars of them, in fact – including Amazon Destinations (a hotel booking site), and its attempt at a smartphone, Fire Phone.

JK Rowling

Much like the titular character of her Harry Potter series, JK Rowling has had quite the bumpy ride on her way to defeating evil (or, in her case, becoming one of the bestselling authors ever, and one of the wealthiest women in the world). Fired from her secretarial job for writing stories during work hours, Rowling was living on welfare as a single mother when she started writing about a bespectacled boy wizard and his pals. She received rejection letters from 12 publishers before signing a deal with Bloomsbury – who warned her she’d need to get a day job if she ever wanted to make any money. Now? She’s the first female ever to become a billionaire author.

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Jerry Seinfeld

We’ve all had that nightmare where we get up on stage to give a speech or perform and… nothing happens. That nightmare became a reality for Jerry Seinfeld the first time he took to a comedy club stage. The moment he stepped in front of the audience, he forgot every single word of his act. Eventually, he was booed and jeered off the stage. The next night, he took the plunge again to applause and laughter (the good kind). He went on to write and star in one of the most successful sitcoms of all time, earning a tonne of dough along the way, and coining a litany of slang we still use today – think ‘close talker’, ‘shrinkage’ and ‘double dip’.

Hillary Clinton

She may have failed in her Presidential bid but, long before that, she was fired from a slightly less prestigious position. Before starting her stint at Yale, Clinton worked her way around Alaska doing odd jobs to make ends meet. As she tells it, she started a job at a fishery, and was handed a spoon and a pair of boots and told to scoop out the insides of the salmon. Before long, her fellow workers were yelling at her for being too slow, and “literally kicked me out”. They gave her a second chance, putting her on a production line packing the salmon. She questioned the quality of the salmon, came back the next day, and the entire operation had vanished. What did she take from this failure? She’s called it the “best preparation for being in Washington that you can imagine”.

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Bill Gates

Notable geek Bill Gates is another tech luminary who has taken note of his failures to pave the road to success. Before founding Microsoft, the former richest man in the world co-founded a company named Traf-o-Data, which designed a computer that processed paper tape from traffic counters. Though this attempt went the same way as the Betamax, he and his business partner Paul Allen learnt from their failures and used them to launched Microsoft. He has said of his successes and failures that, “it’s fine to celebrate success, but it is more important to heed the lessons of failure”.

Anna Wintour

While her name is now one that any fashionista worth her salt is familiar with, Anna Wintour’s sartorial career didn’t get off to a flying start. Beginning her industry tenure at Harper’s Bazaar in New York as a junior fashion editor, Wintour’s shoots were deemed a little too edgy by her editor, who gave her the boot after being in the job for only nine months. Thirteen years later she was sitting in the editor’s chair at US Vogue, where she has remained ever since. Like the others on this list, she has embraced her failure, telling an interviewer, with her notorious candour, “everyone should be sacked at least once in their career because perfection doesn’t exist”. Amen.

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Fred Smith

If you ever need proof that sometimes your uni lecturers don’t know what they’re talking about, look no further than FedEx founder, Fred Smith. Smith pitched the idea for FedEx – a company that would deliver small, high-priority packages late at night to avoid traffic congestion – to his professor at Yale, as part of a business assignment. His professor awarded him a poor mark, which only strengthened his resolve to get his idea off the ground. In his first 26 months in business, Smith experienced $29 million in losses, before bringing in $75 million in his third year. After profits went from $2 billion to $98 million during the GFC, the company tightened its belt, only to experience record high profits come 2013.

Vera Wang

A keen figure skater from the age of eight, Vera Wang competed in the US Figure Skating Championships, but failed to make the US Olympic team. Knowing that she would never be able to compete at the level she wanted, she pursued a career in fashion – and became an editor at Vogue, a position she retained for 17 years. After some time, however, she realised that her second career was stagnating, and that she would never be in line for the editor-in-chief position. From there, she started her now-celebrated bridal gown label and hasn’t looked back. She’s now worth around $1 billion.


Che-Marie Trigg is a freelance writer and full-time subeditor. Her work has appeared in Virgin Australia Voyeur, Collective Hub and GoPlaces with Toyota magazines among others, as well as on websites like Broadsheet and Junkee. Follow her on Instagram @chemariet