How To Face Failure (In Your Career) And Actually Learn From It

For many, being fired from two consecutive high-profile jobs would be enough reason to just call it a day (or at the very least, seriously reconsider their career path),  but then, Sarah Robb O’Hagan isn’t most people.

Once an unemployed Kiwi graduate, O’Hagan is now the chief executive officer of the successful Flywheel Sports, an American sporting company that operates indoor cycling ride studios across the US. She’s also the woman behind the ExtremeYOU movement, designed to help others become their best selves by embracing failure and maximising their potential. And if anyone knows about failure, it’s Sarah Robb O’Hagan.

Less than 20 years ago, O’Hagan was in a very different position. Stranded in a foreign country, laid off and in danger of being deported, the 20-something Sarah Robb O’Hagan was ready to give up on a career in marketing. Fired from her role at Virgin and then laid off from her vice-president of marketing position at Atari Interactive just two years later, she believed her career was officially over. The two experiences, to this day, still make her cringe. “I had to go through the experience of packing my desk into a box and walking through the office with everyone looking at me … twice,” the CEO would later recall in an interview with the Business Insider. “It was awful.”

As awful as it may have been, her predictions of the end of her career wouldn’t eventuate. Not long after leaving Atari, she went on to land a marketing director role at Nike. From there she became the president of multibillion-dollar sports drink company, Gatorade. And, in 2012, she was named president of Equinox Holdings, the parent company of fitness chains Equinox, Pure Yoga, and Soul Cycle. A far cry from the hopeless young marketing graduate at the turn of the millennium, the current CEO of Flywheel Sports is energetic, optimistic and eager to pass on advice to others who may be struggling to get their careers moving.

Sarah Robb O’Hagan acknowledges taking risks and facing failure is a difficult skill for those living in the modern age. “We are in a much more thriving time than our grandparents were and I think when you have less to lose you’re willing to take more risks,” she explains. “Whereas I feel we’re all being raised in a time where we have a lot to lose because life is good, so I think there are real cultural underpinnings to it.”

She believes many people in the work force with a tendency towards conforming and ‘editing ourselves down’ could actually be doing themselves a disservice by not being true to their character. The pressure to conform to business and industry norms is something the CEO and writer has grappled with herself. Describing a time early in her career when she worked for Air New Zealand, Sarah Robb O’Hagan says she would frequently find herself in a state of distress because of this. “At times, I would go home at night in tears because I had to put my presentations together in a way the company liked to do it and it was like speaking a foreign language for me,” the author explains. “I remember saying to my boss, ‘this is it, you should either fire me right now or I’m going to start doing things the way I know how to do them’.”

Dubbing it her ‘Jerry Maguire moment’, her brave decision to confront her boss would eventually pay off – not only for the business but at a personal level. “I was just so much more confident because I was effectively being myself, speaking my own language… as opposed to editing myself into a system that was very foreign to me.” Although she didn’t know it at the time, Sarah Robb O’Hagan’s refusal to conform would later become one of her greatest attributes. A technique she fondly refers to in her book as ‘getting out of line’, she stresses the importance of knowing when to challenge the status quo.


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