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 Siriani (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 FULL SHOW NOTES: https://stackingbenjamins.com/top-5-retirement-plan-regrets-1758 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