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.

FULL SHOW NOTES: https://stackingbenjamins.com/what-is-holding-you-back-from-reaching-your-goals-1713

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

🎧 Dive deeper, grab resources, and check out past episodes at StackingBenjamins.com

Enjoy!

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Allin Cottrell

The AI-powered Podcast Player