Spending Confidently in Retirement with Kevin Sebesta: EDU #2521

Chris’s Summary:
Jim and I are joined again this week by Kevin Sebesta from the Rock Retirement Club in this EDU episode. We explore what helps retirees start spending confidently—especially when markets are volatile or the saver mindset is hard to shake. Kevin shares how structure, support, and community all play a role, and why building confidence takes more than just having a solid financial plan.

Jim’s “Pithy” Summary:
Chris and I bring Kevin Sebesta back this week for round two, and this time we’re talking about what it really takes to start spending confidently in retirement. Kevin’s been retired for over a decade and now coaches others through the emotional messiness of it all—because let’s face it, knowing you “have enough” and actually feeling comfortable using it are two very different things.

We dig into how savers struggle to flip the switch, how things like the Fun Number and Minimum Dignity Floor can give people the permission they need to enjoy their money, and why building in a simple cash reserve might just be the difference between “Hey, let’s upgrade the cruise cabin” and “Let’s sit in steerage because the market dipped 8%.” We talk about community, support, peer influence (yes, even a little friendly shaming), and how watching other retirees live well can sometimes do more than a spreadsheet ever could.

Kevin shares some great anecdotes—including what happens when frugality runs too deep—and I get into my usual rants about emotional risk, the real cost of inaction, and why deferring fun until your 80s is a plan only a masochist could love. Retirement planning isn’t just about having a secure strategy—it’s about creating a life worth funding!

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