Retirement Unscripted, with Joe, John, and Jeff

In this episode of Retirement Unscripted, Timm Glover joins us for a thoughtful conversation about whether it’s possible to “fail” at retirement, ultimately arguing that fulfillment comes not from titles, accomplishments, or work, but from a deeper sense of identity, purpose, values, and personal integration. The discussion explores how life’s challenges often awaken self-awareness, why retirement...

In this episode of Retirement Unscripted, we talk with retired hospice physician Bob Friedman about how years spent caring for patients at the end of life shaped his perspective on retirement, purpose, forgiveness, and living with fewer regrets. Bob shares how nurturing his lifelong passion for music helped him transition smoothly into retirement, turning songwriting, recording, and teaching his g...

In this episode of Retirement Unscripted, the hosts welcome guest David Sunderland, who is approaching retirement with clarity and enthusiasm, sharing how a simple, unscheduled vacation moment sparked his desire to embrace that next phase of life. The conversation explores common retirement challenges—financial readiness, family uncertainty, and identity—while emphasizing that true “freedom” often...

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, entrepreneurship, and the evolving meaning of work, play, and legacy in a noisy modern world. Retirement...

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, creativity, and the anxiety that can follow major life transitions. Clint shares how embracing learnin...

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 friendships, spousal expectations, and embracing openness, learning, and flexibility rather than rigid plans...

In this episode of Retirement Unscripted, we welcome Florence Ricks, who shares her journey of repeatedly “retiring” only to reinvent herself through purpose-driven work, learning, service, and creativity. The conversation reframes retirement as a series of inflection points focused on authenticity, relationships, and making a meaningful difference in the lives of others.

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