Lessons from an Olympic Champion About Wealth and a Meaningful Life

The 2026 Winter Olympic Games in Milan-Cortina, Italy are underway.

By the numbers, the summer games first held in Athens in 1896 dominate with twice the sporting competitions and almost four times more athletes.

But not for Minnesota, the land of five-month winters. In number, Minnesota’s 24 athletes in these Games trail only Colorado with 30, and beyond the number, the athletes are powerhouses in women’s and men’s hockey, Alpine and Nordic skiing, curling, and speed skating.

Our family’s interest in these Olympic games is a story of connection and friendship. Olympic and World Champion Nordic Skier, Jessie Diggins, has announced her retirement from skiing following these winter games.

Jessie was my daughter’s teammate in high school. Since I cooked her dinner and washed her dishes, I feel free to ride her coattails and fame for just this brief note.

National Public Radio interviewed Jessie leading into these games from the Green Mountains of Vermont. Her Olympic gold medal in 2018 changed her life. Except she kept on winning ─ 33 world cup victories and three FIS World Cup titles ─ recognizing the best female skier in the world.

Is this just a trip down memory lane for me, or can we find our own life lessons from someone who’s reached the top of a sport combining complex technique with grueling physical demands, often performed in bitter cold?

Reflecting on her victories, she said in the NPR interview, “You know the award ceremony is the coolest ten minutes of your life, but then it’s over. What you’re left with is the process.” Back to work but finding joy in the practice.

Her purpose has changed, grown up, and become more important. She describes her higher profile as a platform to advocate for mental health for woman in sport, for climate change, and for love, compassion, acceptance of people, all people. “I want to make sure you know who I’m racing for when I get to the start line at the Olympics.”

Having public struggles with eating disorders showed Jessie she needed a team ─ coaches, trainers, teammates, nutritionists, and therapists. “I’m a strong, gritty, tough woman, and I need help. I shouldn’t have to just figure this out on my own.”

With adult children, I think about things differently now. Behavioral finance author Brian Portnoy said it best, “Funded contentment starts with figuring out the stories that define us. It is the ability to underwrite a meaningful life.”

What is wealth to you? Do you take care of your health? What is your most consistent stressful thought or topic? Are you going to be okay?

My children, two of them skiers and one still playing adult league hockey, will send me text updates tracking Jessie’s races. I will still see a clumsy, firebrand girl full of life, grit, and humor moving to Michael Jackson’s Thriller on skit night.

It’s not too much to ask ourselves to add some fun to our wealth planning journey, to ask for help, and to set our sights on something bigger than our station today.

Funded contentment feels like a good start to a meaningful life.

Good luck, Jessie.