There are some time-tested career trajectories that you don’t want to mess with. Getting a Computer Science degree from Harvard and then a job at a top-tier Venture Capital firm is one of them. (Not to mention, Division 1 rowing.) But sometimes you feel a pull. Something awakens in your soul. You need to do something different. So you burn the ships. And go for an Olympic Gold. __In a totally different sport.__ Kristen Faulkner started cycling as a hobbyist in Central Park at 25 years old. Three years later she bailed on her VC career. And at 31 years old, she won Olympic gold. But this wasn’t a high-risk YOLO. It was a __well-executed__ and__bold pivot.__ ## New to RadReads? Hi, I’m Khe Hy. Nearly a decade ago [I quit my 7-figure job on Wall Street]() to become a writer. I explore topics like [money](), [happiness](), [ambition](), [relationships](), [productivity]() and [more](). I also host [The Examined Life Podcast]() where I explore life’s thorniest questions with a different guest each week. My newsletter is the best way to experience my work. Sign up here: ## Overcoming the sunk cost fallacy Faulkner [walked away from a lot.]() She could’ve easily stayed on the VC career track and lived a high-income (and [high-status]()) life. But who wants to [bury a dream]() when they’re only 28 years old? Now Faulkner played her cards right and got the coveted gold medal. But you know what’s even more impressive? She approached [the career pivot]() with a very specific strategy and took numerous steps to de-risk this _risky endeavor_. And even if professional cycling isn’t in the cards for you, Faulkner’s playbook is pure gold. ## 1\. She ran some experiments It’s easy to [fantasize about “dream careers.”]() Maybe [you want to be a DJ.]() Or the CEO of a public company. Or [a YouTuber.]() But being elite at anything requires sacrifices that aren’t always obvious. In [an interview with Voxwomen](), Faulkner explains how she needed to understand if she had “the physical aptitude to succeed as a professional cyclist.” To test if she was ready, she hired a professional cycling coach who: > Analyzed my numbers, built me a solid training plan, and gave me constant feedback on how I was developing as a rider. ## 2\. She put in the work Next there’s the fantasy of the _dream job_. And [the reality of the dream job.]() And usually, the intense gap between the two is where big personal initiatives go to die. Faulkner had a plan to ensure this wouldn’t happen: * She trained __2 hours every weekday__ before work * She raced __every summer weekend__ in amateur races * She used __all her vacation days__ for more competitive races ## 3\. She worked within her constraints A VC job ain’t no walk in the park. There are Zoom calls. Strategy meetings. [After-work networking.]() So Faulkner made some changes to accommodate a more intense training regime. First, __she moved closer to work__ to reduce her commute time. Next, she received permission from her boss “to __start and finish work later every Wednesday__ so she could fit in a 4-hour morning ride.” Lastly, she negotiated with her manager “to __work half-time and remotely for two months__ so that she could race in Europe.” Admittedly, Faulkner had a pretty cool boss. But her “asks” weren’t astronomical. ## 4\. She hit her breaking point Even with all those adjustments, she hit a breaking point. It turns out that full-time racing is not sustainable with a half-time job. That doesn’t mean she didn’t try (emphasis mine): > During the 7-day stage race at Ardèche, __I woke up at 6am everyday to respond to work emails, and then analyzed financial and business documents while in the team car on my way to each stage.__ > > After each stage, __I returned to the hotel around 7pm or 8pm, showered, and ate dinner while on Zoom meetings for work.__ I went to bed at midnight and woke up at 6am the next morning to repeat my routine. Now, she had to decide if it was time to [raise the stakes.]() ## Check out our most popular posts: * [It’s ok to take a walk without headphones]() * [Are you a post-achievement professional?]() * [One day, you’re no longer their favorite person]() * [The joy of leaving money on the table]() * [And one of my personal favorites…]() ## 5\. She made sure she wanted the successful version of the job Some people want to be startup founders – but they don’t want to be putting out fires all day. Others want to run hedge funds – but they don’t want their personal lives to be tied to markets. The successful version of a career, is often not as glamorous as you think. Take this quip about scaling the ranks of a law firm: > Becoming a partner at Big Law is like winning a pie-eating contest only to find the prize is more pie. Faulkner knew that the lifestyle of a professional cyclist was intense: > Racing professionally is very different from training and occasionally racing for fun. As a professional, I would need to move across the world, far away from my friends and family. I would spend most of my time traveling, staying in hotels with roommates, making less money, managing the stress of having to perform, and communicating across cultural and linguistic barriers. I would need to place a greater emphasis on my nutrition and physical health. Training would be much more intense, and I would have to eliminate vacations that did not accommodate my training schedule. But she had fallen in love with the sport and was ready to take the leap. And make the sacrifices. ## 6\. She managed her financial risk This one was a shocker. Before making her pivot, Kristen Faulkner [had not hit her retirement number.]() She didn’t have a financial model that showed that [she could retire early]() and live off the 4% rule. But that didn’t mean she didn’t have a backup plan if cycling didn’t work out. And it was a simple one: > If I didn’t receive a contract with living wage after two years, I wanted to make sure that I had enough savings to live off for six months until I found another full-time job. Yup, she made an [angel investment in herself.]() And this was made easier by the fact that she [lived quite frugally.]() > From the moment I graduated college, I supported myself financially, and I saved my money meticulously. I rarely spent money on vacations, dining out, or luxury items. After four and a half years of working and saving, I finally had enough savings to feel comfortable leaving my job. ## My friends, this is the playbook! Look, 99.9% of us aren’t going to [ditch our cubicles]() to pursue Olympic dreams. But we all have dreams of varying flavors. And Kristen Faulkner shows us that we can take tiny steps. Without blowing anything up. And maybe – just maybe – these little steps will turn into big steps. ## Are you a high-earner going through a career transition? Find purpose, navigate money scarcity and reimagine ambition with our Group Coaching program. [Apply today]()