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Hi there, it’s Jill!
Have you been watching the Winter Olympics recently?
I was following the freestyle skiing competitions and felt thrilled seeing Eileen Gu win three medals: two silver and one gold, adding to her gold medal victory at the 2022 Beijing Winter Olympics.
Today, I want to pause on her story to discover what’s sits behind such extraordinary achievements, and share what I’ve learned from her through a career development lens.
For those of you who’ve been following Anchor Growth for a while, you know I have a soft spot for learning from top athletes 😉.
Let’s dive in.
01
Eileen Gu in 10 Seconds
Eileen Gu is a world-renowned freestyle skier and Olympic gold medalist. Competing at the Winter Olympics in 2022 and 2026, she has earned six medals in total, establishing herself as one of the most prominent figures in winter sports today.
But skiing is only one part of her story.
02
One Athlete, Three Identities
Beyond being an elite athlete, Eileen is also a student at Stanford University and a fashion model signed with IMG, walking for brands like Louis Vuitton and appearing on covers such as Vogue.
On the surface, it’s easy to admire the highlight reel: young, intelligent, talented, and seemingly living three lives at once.
But what often gets overlooked is the discipline and structure required to sustain all three.
Her schedule is demanding by any standard.
She trains and studies during the week, flies across continents on weekends for competitions or fashion events, eats meals in the car to save time, and completes assignments during long-haul flights. Sometimes landing, she would going for a 10km recovery run, and then attending class the next morning.
Jet lag is routine. Pressure is constant. Most importantly, there are no “off” days.
While her work ethic and physical resilience are deeply impressive, what I find most enlightening is how she has structured her life, and what that can teach us about careers.
03
Create Opportunities to Try, With Options to Fall Back On
In The Black Swan, Nassim Taleb introduces the barbell strategy in investing:
allocate 80–90% of your assets to low-risk investments, and use the remaining portion for high-risk, high-upside bets. If the risky part succeeds, the payoff is handsome. If it fails, your downside is protected.
Viewed through this lens, Eileen’s life also resembles a carefully designed portfolio.
The stable pillar: being a Stanford student
With that education and her discipline, she has access to a conventional, high-quality career path if she chooses. This is her safety net.The high-risk, high-reward pillar: freestyle skiing
Olympic success is a rare and life-changing experience for every professional athlete. It’s a credential and a differentiator that last for a lifetime.The amplification pillar: modeling and media presence
This expands her reach beyond sports and academia. Not everyone follows skiing or attends Stanford, but millions engage with and media. Today, she has 3 million followers on Instagram globally and has built extraordinary commercial leverage through sponsorships.
Together, these three pillars form a tripod.
Even if one, or even two underperform, the system remains stable. It’s a structure that allows experimentation, absorbs failure, and creates optionality.
And that’s the real advantage.
Long-term success doesn’t come from never failing. It comes from building a system where failure is survivable, and learning compounds.
04
What Does This Mean for Your Career?
We don’t need Olympic medals, Ivy League degrees, or magazine covers to build a resilient career. What matters is designing a path that allows learning, reinvention, and recovery when plans change.
As AI lowers barriers between roles and automates single-dimensional work, career transitions will become increasingly common. The skills and perspectives you develop in one role may later complement a different function and amplify your advantage.
To achieve that, a well-constructed career is built with purpose. Much like Eileen’s portfolio, it doesn’t rely on one single skillset, but evolves through layered experiences, transferable skills, and intentional pivots.
Try ask yourself:
Where is my “stable base”?
Where am I taking thoughtful risks?
What experiences amplify my long-term options?
Final Thoughts
Eileen Gu’s story reminds us that sustainable success is rarely accidental. It’s often the result of designing a system that allows exploration without collapse.
As you think about your own career, the question may not be:
“What’s the next title?”
But rather:
“What kind of portfolio am I building, and does it give me room to grow, adapt, and try again?”
cheers to your journey.
— Jill
Founder of Anchor Growth Newsletter
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