HeyJaredTake Back Retirement
You're a woman on the cusp of "retirement" naturally feeling some anxiety. We are two financial planners who take this subject seriously (but ourselves less so). We will help you feel more confident about your choices by cutting through the myths and mysteries.
- Indexed episodes, last 90 days
- 5
- Latest publication
- Sep 15, 2026
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- Earliest in this view
- Jul 15, 2026
Latest episodes
143: Am I Allowed? The Permission Paradox, with Dan Haylett (opens the original)
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"The one thing you're guaranteed to run out of is time." Our hosts, Stephanie McCullough and Kevin Gaines, welcome back financial planner Dan Haylett, founder of Humans vs. Retirement and author of The Retirement You Didn't See Coming , to unpack his viral essay "The Permission Paradox." Digging through his own client conversations for patterns, Dan found the two words that came up most were "permission" and "allowed." The people who have saved diligently for decades are often the ones least abl
142: Don't Wait Until 65: Medicare Planning For Gen X And Beyond with Danielle Kunkle Roberts (opens the original)
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"Everything government touches is complicated." - Danielle Kunkle Roberts Our hosts, Stephanie McCullough and Kevin Gaines, bring on Danielle Kunkle Roberts of Boomer Benefits, and author of 10 Costly Medicare Mistakes You Can't Afford to Make . As the title of her book suggests, Medicare isn't free. Believing otherwise is mistake number one! Premiums, deductibles, and coverage gaps are real costs that blindside retirees, especially anyone who leaves the workforce before 65 and needs an ACA brid
141: Estimating Spending in Retirement Calculations: Front-end the Fun! (opens the original)
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"Spreadsheets are great at math; they suck at flexibility." Our hosts, Stephanie McCullough and Kevin Gaines, take aim at the assumption that every retiree spends the same inflation-adjusted dollar amount, every year, until death. It's the number your 401(k) statement spits out, the number the 4% rule promises, and it's wrong in two directions at once! First, it ignores life's lumpiness such as the new roof, the wedding, the pandemic-delayed trip to Greece. These are one-off costs that planners
140: Don't You Dare Call Me Retired: Amy Bernstein on Creativity, Doubt, and Uncoupling Your Worth From Your Paycheck (opens the original)
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"You need to uncouple your self-worth from your income." Amy Bernstein does not like the word "retired". Our hosts, Stephanie McCullough and Kevin Gaines, aren't too fond of the word either. A former journalist and federal government communications veteran, she didn't quit anything cold. She shortened her commute first, then went part-time, then, when the pandemic made her last part-time job untenable, took the final step. What followed was less a plan than experiments guided by whatever sparked
139: What Women Need to Know about Moving Investment Accounts (opens the original)
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"As with all things with the IRS, document, document, document." Our hosts, Stephanie McCullough and Kevin Gaines, explain what actually happens when you move an investment or retirement account from one custodian to another. The mechanics may seem as simple as filling out a form and waiting a few days. But Kevin walks through the fine print that trips up even seasoned advisors. Taxable accounts can usually move without triggering a sale, so cost basis and unrealized gains transfer intact. Retir
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