In this episode, Rory speaks with Michael Kay, former CPA, CFP®, certified life planner, and author of How to Craft Your Chapter X, about why the most important retirement planning has nothing to do with money and everything to do with identity, purpose, and joy. Michael shares how decades of advising high-performing professionals revealed a consistent pattern: most people have no plan for who they'll be once the title is gone. He explains why curiosity is the antidote to identity loss, how embracing discomfort in retirement is a zero-risk proposition, and why grieving the end of a career is a necessary step most people skip. They explore the Wheel of Life as a diagnostic tool, why George Kinder's famous "third question" helps connect values to action, and how retirement reshapes relationships, not just individuals. Michael also shares how his monthly Zoom community gives men a safe space for vulnerability and why he replaced achievement-driven purpose with the Three G's: groundedness, growth, and generativity. Want to know how advisors can help clients, and themselves, craft a meaningful next chapter? Find out the answers to these questions and more in this deeply personal conversation with Michael Kay.

"Rory Henry is a registered investment adviser representative of Arrowroot Family Office. This podcast is published independently through Advis-ROR®, an outside business activity, and does not represent the views of Arrowroot Family Office.  It is intended for informational and educational purposes only and does not constitute investment advice. Michael Kay is not a client of Arrowroot nor was there any compensation for his inclusion in this podcast."