Rolling with Rich


April 28, 2025
How lucky am I? Famed health and wellness podcaster Rich Roll asked me to join him for the third time to record a podcast episode that went live last Thursday.

You can watch and listen to it HERE.  

It was inspiring to ask Rich a few questions since he’s normally doing all the inquiries to his guests. Here are the five questions that I suggested every midlifer should ask themselves. If you listen to the episode, you’ll hear how Rich answered these:

  1. Ten years from now, what will you regret if you don’t learn it or do it now?
  1. How might you curate your life if you knew you’d never retire?
  1. How would your relationships improve if you thought of friendship as a practice (thanks, Jeff Hamaoui)?
  1. What excites you, agitates you, makes you curious, or feel neglected from earlier in your life as these are the breadcrumbs to your purpose?
  1. If a younger person asked you to give them 3 pieces of wisdom you’ve learned that have your “wisdom fingerprints” all over them, what would these be and what’s the origin story of each since our painful life lessons are the raw material for our future wisdom?

I’m doubly-lucky because Rich has agreed to join me in Los Angeles on June 5 for an in-person fireside chat for those of you lucky enough to sign up for this. We’re calling it “Wise and Wild” and during the day, you’ll join all kinds of inspiring MEA guest faculty (including my co-founders Jeff and Christine) focusing on navigating transitions, cultivating purpose, owning your wisdom, and thinking of friendship as a practice. Rich will join me later in the day for a conversation about midlife and beyond and, then, if you pay a little extra, you can join Rich, me and our MEA team for a private happy hour. 

The Early Bird price is just $97 for the day and $147 if you add on the more intimate happy hour. You can learn more about it HERE.

-Chip

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