Ep. 14 — A journey to pickleball and purposeful retirement (Wild Willie)

Meet "Wild Willie", a retired lawyer who refused to let retirement be a sentence to boredom. After 45 years of legal battles, Willie strategically mapped out his freedom years with five purposeful activities to ensure longeivity —pickleball being one of them. In this fun-filled episode, Willie serves up laughs with stories of embarrassing court moments and impromptu pizza deliveries, while also sharing the secret sauce to his 58-year marriage. From pandemic paddle-newbie to passionate player, Willie shows us that retirement isn't about slowing down—it's about finding new courts to conquer! Discover how this grandfather of nine balances family adventures, continued mentoring, and competitive play in a second act that might just be better than the first.

Highlights

• Willie's strategic five-pillar approach to retirement planning that goes beyond finances
• How pickleball became one of his five intentional retirement activities during the pandemic
• His ongoing work as a professional mentor, sharing leadership wisdom accumulated over 45 years
• The unexpected origin story behind his "Wild Willie" nickname
• His 58-year marriage secret: friendship as the foundation of lasting love
• Surviving a devastating financial crisis in the '80s and rebuilding for retirement
• The embarrassing court moment that had everyone laughing (including Willie)
• Why multi-generational family vacations create memories that last a lifetime
• His practical advice for those approaching retirement: plan for purpose, not just pension
• The surprising social connections that make pickleball about much more than just the game

Chapters

00:00 Introduction to Wild Willie

03:06 Leadership and his career as a lawyer

06:33 Happy to have a large number of his grandkids close by

07:51 Golf brought him to North Carolina

08:48 The secret to being married for 58 years

11:53 Transitioning to retirement by truly preparing for it

18:01 Deciding that he was going to start playing pickleball during retirement

21:15 Why having a close knit relationship with his grand kids is important

23:10 Multi generational family vacations

28:48 Embarassing moments on the courts

30:03 Meeting the coolest people on the courts

31:50 Doing what he was told and delivering pizza

33:57 Pet peeve of people not following the rec play rules

35:03 Mentoring the next generation is so important

43:03 "Younger next year" ad staying active is his secret

46:30 The impact of the pickleball community