Want to know what keeps retirees up at night? It’s not what they did—it’s what they wish they’d done ten years earlier.
Joe Saul-Sehy is joined by Jill Sirianni (Frugal Friends), Jesse Cramer (The Best Interest), and Doc G (Earn & Invest), who all pull up chairs in the basement for a powerhouse roundtable on the five regrets that show up again and again when people hit retirement. These aren’t hypothetical “what-ifs”—they’re real stories from a real CFP, sharing tales about people who wished someone had told them sooner.
From botched investment allocations that left people either too risky or too conservative, to tax mistakes that cost tens of thousands, to the heartbreaking pattern of people who saved everything but never actually enjoyed their money—this conversation gets real about what actually matters when you’re trying to retire with confidence (and joy).
The good news? Every single one of these regrets is avoidable. The panelists share what to do now so you don’t become one of these stories later, including the estate planning moves that take ten minutes but save your family years of headaches, and why the biggest retirement regret isn’t financial at all—it’s emotional.
Plus: Doug’s trivia challenge pits the panel against each other for bragging rights, because even serious money talk deserves a little competition.
What You’ll Walk Away With:
• The five regrets that show up over and over in retirement—and the specific moves that prevent each one
• Why your investment allocation in your 40s and 50s might be setting you up for regret in your 60s
• Tax strategies that keep more money in your pocket (because giving Uncle Sam extra is nobody’s retirement dream)
• The simple estate planning steps most people skip—and why your family will thank you for not skipping them
• How to give yourself permission to actually enjoy your money instead of hoarding it out of fear
This Episode Is For You If:
• You’re decades from retirement but want to avoid the “I wish I’d known” moments
• You’re closer to retirement and worried you’ve missed something important
• You want to hear top financial minds debate what actually matters (spoiler: they don’t always agree)
• You’re tired of generic retirement advice and want to hear what real retirees actually regret
• You believe retirement should be about living well, not just having enough
Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201
Enjoy!
Our Topic:
5 Big Retirement Planning Regrets
Our Contributors
A big thanks to our contributors! You can check out more links for our guests below.
Jill Sirianni
Another thanks to Jill Sirianni for joining our contributors this week! Hear more from Jill on her show, Frugal Friends Podcast at FrugalFriendsPodcast.com.
Check out her book Buy What You Love Without Going Broke: An Empowering Personal Finance Guide with a Mindful Spending Plan, Take Control of Your Finances Today!
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.
Doc G
Another thanks to Doc G for joining our contributors this week! Hear more from Doc G on his podcast, Earn & Invest, on Apple Podcasts.
Check out his latest book The Purpose Code: How to unlock meaning, maximize happiness, and leave a lasting legacy.
Doug’s Game Show Trivia
- If a meteor landed on a house today, how much would a homeowner’s annual insurance premium likely increase?
Mentioned in today’s show
- Voices for Good: See how your donation helps kids learn smart money habits and gives you a chance to win a Vegas getaway!
Join Us on Monday!
Colin O’Brady shares how to overcome self-imposed limits, chase big goals, and recharge through challenging experiences like solo treks and long walks.
Miss our last show? Check it out here: Financial Literacy for Kids + Are Annuities Actually Safe? SB1757.
Written by: Kevin Bailey
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