
A top retirement podcast. Roger Whitney, CFP®, CIMA®, CPWA®, RMA, guides you on how to actually do retirement well financially and personally. This retirement podcast isn't afraid to talk about the softer side of retirement. It will teach you how to retire with confidence. Two-time PLUTUS winner for best retirement podcast / blog and the 2019 winner for best financial planner blog. This retirement podcast covers how to create a paycheck, medicare, healthcare, Social Security, tax management in retirement as well as retirement travel and other non-financial issues you'll need to address to rock retirement. Retirement isn’t an age OR a finan...
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<p>💬 Show Notes<br><br></p><p>Wade Pfau, author of The Retirement Planning Guidebook and creator of the Retirement Income Style Awareness (RISA®) assessment joins Roger for a wide-ranging conversation on the big questions of retirement income planning. Wade breaks down why the RISA is a better fit for retirement than a traditional risk tolerance questionnaire, how to think about real estate and reverse mortgages as retirement tools, and what the research actually says about annuities — including when to buy, whether to add inflation protection, and how fixed index annuities with living benefits really work. This podcast is a replay...

<p>Roger Whitney dives into practical strategies for navigating health care before Medicare, sharing insights from retirees, survey results, and listener questions. Together they explore real-world solutions for coverage gaps, timing withdrawals, and managing medical expenses in early retirement.</p><p><br>OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN</p>(00:00) This show is dedicated to helping you not just survive retirement but have confidence in your financial and life decisions.(00:40) Roger introduces the focus: pre-Medicare health care, survey insights, and practical strategies.<p>LISTENER EXPERIENCES AND STRATEGIES</p>(03:00) Roger shares experiences and questions from listeners navigating pre-Medicare coverage...

<p>Roger Whitney shifts from financial planning to the non-financial pillar of relationships, sharing a live conversation with Harry Reis about how to feel more loved and connected in retirement. Together they explore the science behind belonging and loneliness, introduce practical mindsets for deepening relationships, answer listener questions, and close with the team’s latest book recommendations.</p><p><br>OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN</p>(00:00) This show is dedicated to helping you not just survive retirement but have the confidence and clarity to lean in and rock it.(00:27) Roger outlines the month ahead: a focus on...

<p>Roger Whitney wraps up the four-part series on navigating health care before Medicare by introducing a practical decision-making framework using the OODA Loop—observe, orient, decide, act—to help you avoid unforced errors and make a confident judgment call. He walks through organizing your retirement cash flow, estimating MAGI and ACA subsidy eligibility, evaluating COBRA, ACA, and private coverage options, and weighing tax optimization against simplicity and continuity of care. He’s joined by Taylor Schulte of Define Financial to discuss how professionals navigate Roth conversions, Social Security timing, ACA cliffs, and the trade-offs between optimizing for subsidies versus long-t...

<p>Roger Whitney continues the four-part series on navigating health care before Medicare, focusing this week on controlling costs—both through everyday decisions and by understanding how the Affordable Care Act (ACA) subsidy system works now that the expanded credits have expired. He explains the return of the 400% federal poverty level “cliff,” walks through how modified adjusted gross income (MAGI) impacts premiums, shares listener experiences with inflation and subsidy loss, and explores the ethical tension around optimizing for government benefits.</p><p><br>OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN</p>(00:00) This show is dedicated to helping you not ju...

<p>OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN</p>(00:00) This show is dedicated to helping you not just survive retirement, but have the clarity, confidence, and comfort to lean in and rock it.(00:30) Roger introduces week two of the four-part series on health care before Medicare and explains why assumptions about health care costs can shut down curiosity, create false tradeoffs, and delay retirement decisions.<p>PRACTICAL PLANNING SEGMENT</p>(05:05) After last week’s sticker shock, Roger shifts the focus to observing health care options before tackling cost mitigation next week.(05:28) Option #1 — COBRA: how continuation coverage works, who qual...

<p>Roger Whitney kicks off a month-long series on navigating health care before Medicare, introducing Cerberus—the three-headed dog of Greek mythology—as a framework for understanding the biggest challenges retirees face when leaving employer-sponsored coverage. He breaks down the three heads of Cerberus, answers listener questions about retirement planning, and shares recent book recommendations from himself and the team.</p><p><br>OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN</p>(00:00) This show is dedicated to helping you not just survive retirement, but have the confidence to lean in and rock it.(00:30) Roger introduces the Cerberus framework and outl...

<p><br>As the Retirement Plan Live series wraps up, Roger Whitney shares wisdom from retirees further along the path to help Henry and Lucy think beyond the numbers. Listeners in their 50s, 60s, and 70s reflect on purpose, work, health, money, and joy—offering perspective on what really matters when retiring early. Roger closes with his own observations from decades of coaching, a Smart Sprint focused on learning from others, and listener-submitted words for the year.</p><p>OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN</p>(00:00) This show is dedicated to helping you not just survive retirement, bu...

<p><br>As the Retirement Plan Live case study continues, Roger Whitney helps Henry and Lucy move from dreaming to feasibility, organizing the real financial resources available to support an early retirement in their 40s. This episode centers on trade-offs, confidence, and the reality of giving up earned income decades early. Roger and the couple walk through income assumptions, assets, and risk tolerance before closing with listener advice, a Smart Sprint, and words for the year.</p><p>OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN</p>(00:00) This show is dedicated to helping you not just survive retirement, but...

<p>As the Retirement Plan Live case study continues, Roger Whitney helps Henry and Lucy articulate what they want their FIRE retirement to actually look like—starting with values, dreaming without constraint, and then translating that vision into concrete goals. Along the way, Roger shares wisdom from older retirees about purpose, productivity, and flexibility, invites listeners to reflect on their own “magic,” and closes with a Smart Sprint and listener-submitted words for the year.</p><p>OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN</p>(00:00) This show is dedicated to helping you not just survive retirement, but to have the co...