Retirement Roadblocks & Resilient Planning: The Squirrels Gone Wild Edition (SB1676) | The Stacking Benjamins Show Podcast

Retirement might be the goal, but the journey? Full of curveballs. On today’s episode, Joe Saul-Sehy is joined by special guest co-host Len Penzo of LenPenzo.com, along with OG and Neighbor Doug, for a no-holds-barred look at what really derails retirement plans—and how to build a strategy that can handle the chaos.

From unexpected job loss to rising long-term care costs, adult kids moving back home, and even changing relationship dynamics, this episode dives into the often-overlooked risks that can chip away at your retirement dreams.

Inside the episode:

What to consider when evaluating long-term care insurance

How job instability late in your career can throw off your timeline

The growing trend of adult children impacting their parents’ retirement

Grandparents becoming full-time caregivers—and the financial toll that brings

Relationship shifts and widowhood in retirement

Downsizing, austerity planning, and staying financially flexible

Plus, our TikTok Minute features Gary V on why taking a step backward might be the smartest move forward. And as always, Doug brings the trivia heat—this time, with a nostalgic nod to a certain potato-headed toy.

With Len Penzo in the basement, the insights (and squirrel references) are extra sharp. Prepare to laugh, learn, and rethink what “retirement ready” really means.

FULL SHOW NOTES: link

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Enjoy!

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