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In this episode of Retirement Unscripted, the hosts welcome entrepreneur Maggie Kuyper for a cross-generational conversation about redefining retirement as freedom of time, identity, and purpose rather than a fixed age or finish line. Together they explore financial anxiety, comparison culture, ent…

Episode 1

The very first episode. Joe, Jeff, and John discuss their backgrounds and how they are adjusting to a new chapter of life.

Jeff Pickering

In this episode, we talk with Jeff Pickering about his transition toward retirement, focusing on the emotional tipping points, identity shifts, and uncertainties that come with stepping away from a long career in sales. The conversation explores the importance of relationships, intentional friendsh…

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This episode explores the universal question, “What’s next?” through a conversation with entrepreneur Clint Smith, who reflects on life after selling the software company he co-founded. Drawing parallels between exiting a business and retirement, the discussion examines identity, purpose, family, c…
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