Retirement Roadblocks & Resilient Planning: The Squirrels Gone Wild Edition (SB1676)

The Stacking Benjamins Show

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: https://stackingbenjamins.com/four-things-that-can-derail-your-retirement-plan-1676

Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201

Enjoy!

Learn more about your ad choices. Visit podcastchoices.com/adchoices