Swimming Was Just the Start: Finding Fulfillment After Sport
After a standout swimming career, Caitlin Olliff spent years navigating uncertainty – until patience and persistence led her to a life she is proud to claim.
Caitlin Olliff had spent most of her life in the water — a decorated swimmer, All-American, and Olympic Trials finalist who built her identity around early mornings and relentless pursuit. But as she approached the end of her final semester at the University of Arizona, a quiet question began to surface: What comes next when the only thing you’ve ever known… ends?” Read about her journey here.
Caitlin sat on a plane, flying back from visiting her sister in Los Angeles. She had just wrapped up a few carefree days — family time, sunshine, a brief break from the day-to-day.
But as her flight took off, she started crying.
“I didn’t want to go back to Tucson,” she said. “That life I was living — it didn’t feel like mine anymore.”
Swimming, the thing that had shaped her life for over a decade, was over. The tunnel vision had cleared, and with it, the version of her life she thought she wanted.
That was the first moment she knew: something must change.
The Ending She Did not See Coming
Caitlin’s path through sport was marked by commitment and routine. Swimming was more than an identity — it was a lifestyle. Early morning lifts, long hours in the pool, academic challenges layered on top. She had always shown up, done the work, and stayed the course.
But when her athletic career ended, there was no real conversation about what came next.
“No one asked me what I wanted to do. Not my coaches. Not my parents. It just wasn’t something we talked about.”
She graduated in 4.5 years and returned home to Denver, ready to job hunt — and immediately hit a wall. Applications went ignored. She didn’t know how to build a resume or write a cover letter. She hadn’t gone to career fairs. She didn’t know where to turn for help.
“I just didn’t think it would be so hard,” she said.
Following the Wrong Things — Until They Taught Her What Was Right
Like many athletes, Caitlin defaulted to what she knew. She got a coaching job at a junior college in Florida where she liked the structure and was also able to lean into strength and conditioning.
But she knew, almost immediately: this isn’t it.
“I knew coaching wasn’t what I wanted long term. But I needed a job. I needed something.”
From there, she pursued a master’s degree at the University of Miami, interned in athletic communications, and got involved with big events like Wodapalooza — a major CrossFit competition that sparked her deepening connection to the sport. Although her part in running the event brought moments of excitement, something still felt out of sync.
“It felt like something was always missing,” she said. “I was trying so hard to make it fit, but it didn’t.”
The One Thing She Wouldn’t Do: Settle
Caitlin and her partner moved to Colorado to build their life closer to family. She bounced around jobs she didn’t love—swim schools, rec centers, early mornings, and odd hours.
She wasn’t afraid of hard work. She just knew she deserved more.
“I didn’t feel fulfilled. I didn’t feel proud. And I knew I didn’t want to live that way forever.”
What she didn’t do — even through doubt, financial stress, and a constant sense of disorientation — was settle.
Eventually, a casual connection at her gym passed her name along to a roommate. That roommate worked in finance and needed someone at the front desk of his firm.
It wasn’t glamorous. But it was a start.
And for the first time in years, Caitlin felt a spark of excitement. She found herself curious, motivated, and growing. That front-desk job led to more opportunity, and eventually, to her current role as a finance analyst at Lockheed Martin.
“I finally felt like I belonged somewhere,” she said. “And when people asked where I worked, I felt proud to say it.”
On Patience, Pride, and Reclaiming a New Identity
Caitlin’s story isn’t a straight line — but it’s marked by clarity, courage, and a deep refusal to stay stuck in something that didn’t feel like her.
“I watched people in my life stay in jobs they didn’t love. I knew I couldn’t do that. Even if my path looked messy from the outside, I wasn’t going to settle.”
She now sees how much of that grit came from her time as an athlete. And how the traits that made her successful in the pool — discipline, drive, self-awareness — showed up even louder outside of it.
When asked what advice she’d give to another athlete, or to her younger self, Caitlin didn’t hesitate:
“Be patient. Use your time wisely. Keep searching. You can work and make money — but don’t stop looking for the thing that speaks to you. When you find it, give it a real shot.”
Life is Bigger Than Sport — Even If You Can’t See It Yet
These days, Caitlin doesn’t lead with her athletic background. She doesn’t introduce herself as an All-American, even though she is.
“Swimming was a part of my life, and I’m proud of it. But it’s not who I am anymore. If someone’s going to be in my life, they’re going to like me for me — not because I swam fast in college.”
She wishes someone had helped her see that earlier — helped her imagine a future that wasn’t centered on sport, but built around values, purpose, and joy.
“Back then, I couldn’t imagine Boomer (her partner), or our future kids. I couldn’t see anything past practice, the next meet, the next lift. But now? Now I know there’s so much more. Life is so much bigger than swimming. And I’m just getting started.”
Have you ever found yourself at a crossroads, unsure of what comes next? Caitlin’s story reminds us that it’s okay to take time to figure it out.
We’d love to hear your experiences — what did your journey of transition look like? Share in the comments!
And if someone in your life could benefit from this message, feel free to pass it along. You never know how your story might inspire someone else.