Tom Henske is a former collegiate goalkeeper and three-time national champion at the University of Virginia whose path after soccer unfolded very differently than he expected. After recurring shoulder injuries brought his playing career to an end, Tom found himself facing the uncertainty of life beyond sport — eventually beginning a career in financial planning that would span more than three decades.

In this episode, Tom reflects on the lessons goalkeeping taught him about resilience, recovering from mistakes, and putting in the work when no one is watching. He shares how returning to soccer as a high school goalkeeper coach gave him an opportunity to mentor the next generation, and how those experiences ultimately sparked a deeper interest in helping young people understand money and prepare for life beyond athletics.

Now a professor of personal finance working with students and student-athletes at UVA, Tom has brought his career full circle. He helps athletes build the financial confidence and habits they can carry long after their playing days are over. Tom discusses financial literacy in the age of NIL, the importance of starting early, and why confidence with money can create greater freedom to pursue purpose and eventually, pay it forward.

Tom is also continuing to bring these ideas to a wider audience. His recently released TEDx Talk was selected as an Editor’s Choice by TED, furthering the conversation around financial literacy and empowering the next generation to build confidence with money.

Watch Tom’s TEDx Talk: https://www.youtube.com/watch?v=4GpcY-mAIRc

Connect with Tom: https://www.totalcents.com/about

This conversation is about navigating unexpected transitions, trusting the skills sport gives you, playing the long game, and finding meaningful ways to use what you've learned to help the people coming after you.

Shahar Biran is a former collegiate tennis player competing at Old Dominion University for undergrad, and then completing her MBA while finishing her final year of eligibility at the University of South Carolina. Like many international athletes, her transition to college athletics required adjusting not only to a new country, but also to a completely different style of competition — trading the independence of individual tennis for the dynamics of being part of a team.

After graduation, Shahar found herself navigating the uncertainty that often follows an athletic career. Inspired by her own experience of navigating the college recruiting process without much guidance, she now works with Momentum NYC, a recruiting agency that helps international junior tennis players pursue opportunities to compete and study in the U.S. Through her work, she now supports athletes through every step of the journey, from recruitment and academics to visas and settling into college life.

In this episode, Shahar reflects on the challenges of leaving competitive tennis behind, the unexpected feeling of missing the pressure and adrenaline of competition more than the sport itself, and how she has found a new outlet for that competitive energy by helping the next generation of athletes. She also shares her perspective on navigating cultural transitions, embracing life beyond sport, and learning to let go of the "all or nothing" mindset that once defined her athletic career.

Brett Stern is a former collegiate tennis player whose life revolved around pursuing excellence on the court from a young age. After training at one of the country's most elite tennis academies and competing at both UC Irvine and the University of Florida, Brett faced a reality many athletes encounter: letting go of the dream that had defined so much of his identity.

In this episode, Brett reflects on the difficult transition away from competitive sport, the loss of structure and purpose that followed, and the challenge of building a new life beyond athletics. He shares how the mindset that fueled his tennis career — resilience, problem-solving, discipline, and persistence — became the foundation for his success in business, where he has spent the last three decades working alongside his father in the family business.

Brett also discusses the importance of finding fulfillment in new pursuits, and learning that purpose can evolve over time. Through honest reflection and hard-earned perspective, he offers reassurance to athletes navigating uncertainty and reminds us that growth often happens long after the final match is played.

Madeline "Maddie" Davis Tully is a former collegiate rower at Princeton University whose athletic journey carried her from the Ivy League to the U23 U.S. National Team and the World Rowing Championships. After stepping away from elite competition on her own terms, Maddy transitioned into coaching, where she spent over two decades developing athletes and helping to build championship programs at Stanford, Ohio State, and Boston University.

In this episode, Maddy reflects on the two major transitions that shaped her life: retiring from competition and, years later, leaving a coaching career that had defined her identity. She shares how each transition required letting go of a role she deeply loved while trusting that something meaningful could exist on the other side.

Now the founder of her own leadership and performance coaching practice, Maddy works with high-achieving professionals navigating seasons of growth and change. She discusses the importance of moving toward something—not simply away from something—the lessons athletics continue to teach long after competition ends, and how redefining success can create space for a more intentional and fulfilling life.

This conversation is a thoughtful reflection on identity, leadership, purpose, and embracing the next chapter with confidence.

Maddy's leadership and performance coaching practice can be found at https://www.mdtlead.com/

Lae Kollasch is a former track and field athlete whose collegiate career took her from the University of Northern Iowa to the junior college level. As her priorities began to shift, Lae realized she could no longer give the sport everything it deserved, leading her to make the difficult decision to step away from competition and begin redefining her identity beyond athletics.

In this episode, Lae reflects on the emotional challenges of leaving behind the athlete identity she had carried for years, describing the transition as an "ego death" and opening up about the mental health struggles that followed. She shares how leaning on her support system, embracing uncertainty, and allowing herself the freedom to change directions helped her move forward.

Lae also shares how she built a career in the fitness industry from the ground up after relocating to Phoenix, eventually launching Offsite Pilates, her own mobile fitness community. We talk about entrepreneurship, creating spaces where people feel connected, and how the lessons she learned as an athlete continue to shape the way she coaches today. This conversation is an honest reminder that leaving sport doesn't mean leaving behind everything it taught you.

Dillon Schoen Toohill is a former Stanford lacrosse player and team captain whose transition out of athletics unfolded alongside one of the most challenging seasons of her life. After losing her father just before her senior year, Dillon found herself navigating both the emotional weight of grief and the identity shift that comes with stepping away from a sport that shaped her for years.

In this episode, Dillon reflects on her decision to pursue a career beyond lacrosse, earning a master’s degree at Stanford before building a career in finance and strategy with roles at Apple and in the digital health space. She shares how athletics prepared her for the demands of professional life while also opening up about the uncertainty that followed the end of her playing career.

Dillon discusses the ways she has stayed connected to sport through endurance challenges that honor her father’s memory, including half-Ironman races and fundraising efforts for cancer research. Additionally, she offers a unique perspective on supporting her husband through his own transition out of professional football, as they navigate the opportunities and unknowns that come with life after sport together.

This conversation explores identity, grief, resilience, and the reality that growth often happens in the seasons when life doesn't go according to plan.

Brandyn Curry is a former Harvard basketball player whose athletic journey took him from the Ivy League to professional basketball overseas. After graduating, Brandyn spent several seasons playing professionally in Europe before a devastating knee injury in Romania ended his playing career and forced him to confront life beyond the game sooner than expected.

Now serving as Program Director for The SHIELD Foundation, Brandyn helps former athletes navigate the often-overlooked challenges of transitioning out of sport. In this episode, he shares the realities of a career-ending injury, the emotional and physical toll of losing the game he loved, and how that experience ultimately led him to a new purpose.

Brandyn reflects on the importance of advocating for your own health, building meaningful relationships before, during, and after your athletic career, and why the lessons learned through sport can continue to shape life long after competition ends.

This conversation explores identity, resilience, and what it means to turn one of life's hardest setbacks into an opportunity to help others find their next chapter.

Aubrey Peterson is a former Division I softball player at the University of Utah and a longtime member of the Great Britain national softball team. Competing internationally for seven years, Aubrey traveled the world while balancing the transition from collegiate athletics to the reality of becoming an independent athlete — navigating sponsorships, training, and life beyond the structure of college sports.

In this episode, Aubrey reflects on the unexpected turns that shaped her transition out of elite competition. After COVID paused international play at the height of her career and injuries shifted her perspective on returning to the game, she began building a new life rooted in community, outdoor adventure, and coaching. Now based in Bozeman, Montana, Aubrey owns and operates a batting cage facility while staying connected to sport in a new way.

She shares honest insight into athlete identity, burnout, retirement, and the importance of separating who you are from what you play. This conversation explores trusting yourself through uncertainty, finding purpose after sport, and redefining what it means to stay competitive long after the game ends.