Who Cares?

You Have Endless Amounts Of Money... What Do You Do NOW?

Episode Summary

Why We Struggle to Imagine Life After Success...Can You? What would you do if you never had to trade time for money again? In this episode of the Who Cares? Podcast, Jeff Jackel and Jay O’Brien run a ruthless (and funny) audit on “time well spent.” If money were infinite, would you still read business books, binge niche podcasts, and optimize your calendar—or would those motivations evaporate without ROI?

Episode Notes

We dig into: 

• purpose vs. productivity: are your “interests” secretly utility in disguise? 
• work you’d do for free: speaking, advising founders, making deals—when the driver isn’t dollars. 
• passion projects that create flow: woodworking, wine, art/design, and a wild genealogy case study (printing 400-page family history books). 
• the accumulation trap: why “enough” is a moving target and how to step off the hamster wheel. 
• travel + friendship in the social era: intense, camp-style bonds that used to fade—now they linger in your feed. 
• retirement reality: you don’t need “endless money” to test this—design days you’d love now. 
• the humor & truth of “10 lbs in a 5-lb bag”: busyness, lateness, and why we overcommit by default. 

Takeaway: build a life where your calendar would look the same whether or not you were paid. Identify the few pursuits that reliably put you in deep work/flow—and architect your weeks around them. 

Drop a comment: if you never had to work for money, what would you do all day for the next 60 days? How long before it gets stale? 

Be honest.