What if the scariest part of retirement isn’t running out of money—but losing your sense of identity? This week on The Stacking Benjamins Show, we tackle the fears that hold so many people back from financial independence and a joyful, purpose-filled retirement.
Joe Saul-Sehy and Doug are joined by an all-star panel of financial thinkers:
- Mark Trautman (Mark’s Money Mind)
- Paula Pant (Afford Anything)
- Jesse Cramer (Personal Finance for Long-Term Investors)
Together, they unpack the emotional, practical, and strategic side of planning your next chapter—whether you’re closing in on retirement or still working toward it.
- The biggest fears about retirement: from running out of money to running out of meaning.
- The “one more year” syndrome: why it’s so tempting to delay and how to break through.
- Time freedom vs. financial freedom: how to align your life goals with your money strategy.
- Tactics to conquer fear: income layering, diversified portfolios, annuities, and rental properties.
- Psychology matters: why no spreadsheet ever solved a midlife identity crisis.
- Real stories from the panel: wins, struggles, and lessons from guiding others through retirement transitions.
- Planning for healthcare and long-term care: because your body didn’t get the early retirement memo.
- Plus, the usual basement mayhem: trivia, playful host banter, and a few unexpected laughs (we won’t call them “funny”—you know the rule).
- Retire to something, not just from something. Purpose beats spreadsheets.
- Understand your income plan. Know where the money will come from, rain or shine.
- Plan for healthcare now, not later. Medicare, long-term care, and medical surprises deserve your attention.
- Don’t go it alone. The best plans are ones you understand, but it helps to get advice from trusted sources.
Whether you’re on the cusp of calling it quits or still deep in the grind, this episode will help you prepare—not just financially, but mentally and emotionally—for a retirement you’ll love.
Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201
Enjoy!
Our Topic:
Fear Will Hold You Prisoner; a Diversified Portfolio Will Set You Free (Millennial Revolution)
During our conversation, you’ll hear us talk about how fear can creep in as you approach retirement—and how a clear income plan and a well-diversified portfolio can help quiet the noise. We dig into the emotional hurdles like the “one more year” syndrome, explore the difference between financial freedom and time freedom, and share real experiences from people who’ve helped others navigate this transition.
Our Contributors
A big thanks to our contributors! You can check out more links for our guests below.
Mark Trautman
Thanks to Mark Trautman for joining our contributors this week! Hear more from Mark on his show, Mark’s Money Mind at marksmoneymind.com, and check out his YouTube channel, where he shares money lessons, personal stories, and community wisdom to help you create a stress-free life of financial freedom: Mark’s Money Mind on YouTube.
Jesse Cramer
Another thanks to Jesse Cramer for joining our contributors this week! Hear more from Jesse on his show, Personal Finance for Long-Term Investors – The Best Interest, on Apple Podcasts.
Learn how you can work with Jesse by visiting The Best Interest – Invest in Knowledge.
Paula Pant
Check out Paula’s site and amazing podcast at AffordAnything.com
Follow Paula on Twitter: @AffordAnything
Doug’s Game Show Trivia
- While Peyton Manning earned a whopping $16 million in 2016, how much did his brother Walter Payton make in 1979 when he was the second-highest paid player in the NFL, just behind O.J. Simpson?
Mentioned in today’s show
Join Us on Monday!
Tax laws are shifting again. We’ll break down the biggest new planning opportunities STACKERS need to know to stay ahead of the game.
Miss our last show? Check it out here: Understanding Your Financial Roadmap (with Nick Maggiulli) SB1712.
Written by: Kevin Bailey
Leave a Reply