The Cookie Jar: Gamifying Post-Retirement Plans

Today, I'm thrilled to welcome Fritz Gilbert back for his second appearance on the podcast. Fritz is an award-winning blogger and author of The Retirement Manifesto, one of the most influential retirement blogs in the country. He has now been retired for six years, and while many people think the big transition ends the day you leave the workforce, Fritz's journey proves that retirement continues to evolve in meaningful, surprising, and deeply personal ways.

Recently, he announced he is stepping away from full-time blogging to spend more of his life "outside the walls," shifting his time toward family, exercise, charitable work, and the flexibility that first drew him to retirement. Fritz explains why stepping back wasn't a loss—it was a necessary reshuffling of cards in the ongoing "game of retirement poker."

In our conversation, Fritz discusses the surprising emotional journey of redefining retirement. He explains why he has never struggled with boredom, depression, or identity loss, and highlights how he avoided the most difficult retirement phase that nearly 70% face.

We also talk about one of the most overlooked elements of retirement satisfaction: giving yourself permission to spend your money—or gift to your kids—while you can enjoy the benefits, rather than clinging to your savings out of habit or fear. Fritz explains why intentional spending is not only rational but also often essential for living a fully realized, purposeful retirement.

In this podcast interview, you'll learn:

• How Fritz avoided boredom, identity loss, and the infamous "retirement dip."
• The surprising emotional transition his wife experienced after caregiving.
• Why replacing the non-financial benefits of work is a must.
• How to refine a bucket strategy and reduce interest-rate risk in retirement.
• The real challenge of Roth conversions and why liquidity matters.
• Why many retirees spend too little and how Fritz overcame that fear.
• How to support adult children without jeopardizing their independence.
• Why the 90/10 rule becomes unavoidable in retirement.

Show Notes: HowardBailey.com/537

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