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Retired cyclist Amy Charity.The Globe and Mail

A low point in Amy Charity's racing career was when she had to spend a night sleeping in a cellar, on a deflating air mattress, next to a teammate, with a cat on her head.

An even more painful one, but still drawing her infectious laugh, was when her shoulder ripped up in a crash. There she was, having quit a career in finance to race bikes full time, recovering from a severe acromioclavicular shoulder tear for eight weeks, when she desperately needed to get back on the bike.

In bicycle racing, particularly women's racing with its smaller sponsorship money, every race, every result not only counts toward possible selection for the national team, each counts toward the team even extending a racer's contract for another season. Eight weeks incapacitated are excruciating, to say nothing of the many other crashes.

In order to race full time, Ms. Charity had left everything she had worked for professionally during her years of climbing the corporate ladder in the financial sector.

"In my mind at the time – it's so funny to think about it – but there was nothing in the world I wanted more than to be a professional bike racer. It was worth trading off everything," she said by phone from her home in Steamboat Springs, Colo.

By all accounts, Steamboat Springs is wonderland, an unspoiled ski resort during the snowy season, an idyllic cycling town every other season, with endless, beautiful roads and Denver a distant three-hour drive away.

But Steamboat Springs is also a hard place to find professional work. And Ms. Charity had a financial-sector job, a good one, working in investor relations for a $2-billion hedge fund, "essentially talking to potential investors, and finding new investors and answering the first line of questions that they had."

She loved the job. She had spent nine years before that, fresh from university, working her way into senior management with the credit-card company Capital One, a job that moved her to various cities, including Nottingham, England, where she met lasting friends and her future husband, and got into cycling as a hobby. Having grown up as a swimmer, she got serious one year and competed in Ironman Switzerland.

Yet her financial career remained her priority. After returning to her home state of Colorado, she took the job with the hedge fund. "Things were really, really good."

Then came the summer of 2013, and cycling took over.

There are times in everyone's life when an alternate path becomes a possibility. And there are a million reasons why we don't follow it: reliance on a steady paycheque, a pension. Maybe a spouse's career or kids override the dream. Maybe accepting a steadier existence becomes the dream itself.

Ms. Charity's dream unfolded when a friend suggested trying an uphill race, the Lookout Mountain Hill Climb in Golden, Colo. They drove through a snowstorm to get there. It was her first race, so she competed in the novice Category 4. "And I ended up winning that. I was like, 'Wow, that was so fun.' I just got the bug for it. So I spent the rest of the summer doing every race that I could," she said.

She rose to Category 2 by season's end, which is no easy feat. In many races, Cat 2s will compete with the pros. The next year she was Cat 1, the highest level of racing without a professional team contract. She was competing in events such as the five-day Tour of the Gila stage race in New Mexico against top women's teams.

"That's when I started sending my résumé to pro teams. I got rejected by all of them," she said, again with her infectious laugh. Most teams ignored her, despite her stellar showing at races. One team, though, did get back to her, noting that Ms. Charity's age at the time, 35, was the only reason that it didn't sign her. But a fortuitous friendship with the U.S. head of the Wilier bicycle company helped introduce her to the small Vanderkitten women's team.

"I was not a paid rider my first year. They said, 'You'll get bikes and everything you'll need,' but that was it. It was terrifying," she said. Her hedge-fund employers also said she needed to choose between finance or full-time racing.

"It was the hardest decision," she said. "In my whole life after college, I had health insurance, potential bonuses, a salary and a lot of comfort. And all I had when I left that job was a contract that said, 'Here are the races that we'll do, and you may or may not race in these races.'"

She ended her first season in the red, having spent thousands more out of pocket to get herself to races than the actual prize money the team shared. She came closer to breaking even in her second year, a season which included competing for the U.S. women's cycling team in Europe, the highest level of pro racing. She was a domestique, a role in which she had to shelter the team leader and do everything to keep her in a good position in the pack of riders.

In her third year, Ms. Charity had joined the larger, dominant North American cycling team Optum (now Rally Cycling) and was given a nominal salary. Not enough to pay the grocery bill, "but at least you can sort of get by."

She had to rely on her savings. Her husband, Matt Charity, had been a competitive cyclist in Britain in the early 1990s, so he understood. He was encouraging, but her racing career required both to adopt a minimalist lifestyle. "I became the most frugal person ever. In hotel rooms, I was like, 'Awesome, free shampoo.'"

At the end of 2015, in her late 30s, she retired from cycling after a significant accomplishment, competing at the 2015 world championships in the team time trial. She has since written a book about her cycling years, The Wrong Side of Comfortable, gives talks and works for a non-profit organization promoting Steamboat Springs.

She's also retiring at a time when cycling suddenly has other options for talented riders to make money in mass-start events, such as Gran Fondos (long, timed rides for mass participants in which the front tends to be a competitive race, like a city marathon) and gravel grinders (the same idea but on gravel and off-road). It's a way for pros and retired pros, especially those who remain in the public eye such as Ms. Charity, American Alison Tetrick and Canadian Emily Batty, to earn prize money and sponsorship fees.

It's different than the pressures of fulltime team racing. "I have to tell you that racing is so hard, when you're in that lifestyle. There were days when I was like, 'I can't wait to sit at a desk and drink a coffee,'" she said. Still, "I didn't want to be 50 or 60 years old and say, 'I had some talent as a cyclist. I wonder if I could have raced in Europe.' You don't want to live with that could-have-been in the back of your mind."

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