Big goals often look simple until you are in the middle of them, tired, uncertain, and second-guessing everything.
How do you stay steady when the plan shifts? How do you prepare for the parts you cannot predict?
In this episode, Josh Leonard shares how a grueling 60-mile mountain bike race deepened his view on preparation, mindset, and the importance of thinking ahead. He talks about the parallels between physical endurance and retirement planning, the value of support systems, and how steady habits create a more intentional life.
Key points:
- Planning missteps that made the Austin race tougher, and why preparation shapes outcomes
- How heat, hydration, and equipment choices influenced the long ride and its lessons
- Why support systems matter when facing difficult moments or big goals
- How intentional preparation mirrors the steps needed for retirement planning
- The value of seeking growth at every stage of life and staying engaged
- And more!
Resources:
Connect with Josh Leonard:
Popular Podcasts
Stuff You Should Know
If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.
The Joe Rogan Experience
The official podcast of comedian Joe Rogan.
Two Guys, Five Rings: Matt, Bowen & The Olympics
Two Guys (Bowen Yang and Matt Rogers). Five Rings (you know, from the Olympics logo). One essential podcast for the 2026 Milan-Cortina Winter Olympics. Bowen Yang (SNL, Wicked) and Matt Rogers (Palm Royale, No Good Deed) of Las Culturistas are back for a second season of Two Guys, Five Rings, a collaboration with NBC Sports and iHeartRadio. In this 15-episode event, Bowen and Matt discuss the top storylines, obsess over Italian culture, and find out what really goes on in the Olympic Village.