Ian Sylves is a former collegiate and professional hockey goalie whose relationship with the game began almost as soon as he could walk. Growing up in Buffalo, New York, Ian spent much of his life on the ice before eventually playing Division III college hockey and continuing his career professionally, including time overseas. After years of pushing through injuries, deteriorating back issues ultimately forced him to step away from the sport before he was ready.

In this episode, Ian reflects on the difficult reality of leaving hockey when his body made the decision for him, and the identity shift that followed. He shares how navigating ongoing health challenges, the loss of his father, and uncertainty about what came next forced him to rethink what he wanted his life beyond hockey to look like.

Ian also discusses how the qualities he developed as a goalie — discipline, emotional control, adaptability, coachability, and learning to recognize patterns — continue to shape his work today in financial planning and his approach to coaching the next generation of goalies. Through his story, Ian offers a thoughtful perspective on accepting the unexpected, finding purpose beyond competition, and recognizing that the lessons learned through sport can continue to serve you long after your playing career ends.

Want to connect with Ian? Find him on LinkedIn here: https://www.linkedin.com/in/iansylves/?isSelfProfile=false

Genevieve Henderson, is a former collegiate soccer player, therapist, business owner, and the host of What the Hell Do I Do Now? In this 100th episode, Gen reflects on a career and life path that has been anything but linear, sharing how unexpected changes, setbacks, and new opportunities ultimately shaped the work she does today.

After stepping away from collegiate athletics, Gen moved through coaching, fitness, graduate school, clinical work, and private practice before realizing how deeply her experiences as an athlete connected her to her work as a therapist. She shares how the podcast, which began as a passion project, eventually became a meaningful way to support athletes navigating the transition out of sport.

Gen also reflects on the identity disruption that comes with leaving athletics behind and the common themes she has heard throughout 100 conversations with athletes. She discusses why your athletic identity doesn't simply disappear when your sport ends, the importance of honoring what sport has given you while discovering who you are beyond it, and why the first year after sport can feel especially disruptive.

Through her own experiences with imposter syndrome, the pressure to prove herself, and the tendency to equate productivity with worth, Gen offers an honest look at the process of building a life beyond athletics. This episode is a reminder that there is no single path after sport, that it's okay for your journey to change direction. The person you become after athletics can still carry the best parts of who you were as an athlete.

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.