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PODCAST

Retirement Answer Man

Roger Whitney, CFP®, CIMA®, RMA, CPWA®

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

business investing

All Episodes

41:58

Listener Questions: Should I Take Social Security...

Retirement Answer Man ·

2026/04/08

In this episode of the Retirement Answer Man, Roger Whitney explores the critical decision of when to claim Social Security benefits, weighing the pros and cons of taking them early versus delaying. Through listener questions, he delves into the impact of investment returns, health considerations, and income needs on retirement strategies. Roger also shares inspiring retirement stories and offers practical advice on managing retirement accounts and planning for the future. With insights

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42:50

Listener Questions: Should I Move My 401K into an IRA...

Retirement Answer Man ·

2026/04/01

Explore how meaningful travel experiences, storytelling, and thoughtful planning can enhance your retirement journey. In this episode, Roger answers listener questions on managing retirement accounts, health insurance, financial literacy, and shares inspiring stories and book recommendations.OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN(00:00) Introduction: Rock retirement with community questions and storiesROCKIN’ RETIREMENT IN THE WILD(01:39) A memorable travel story from Doug in

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59:32

Why Even the Best Retirement Calculator is Wrong

Retirement Answer Man ·

2026/03/25

Roger Whitney explores why retirement planning software—especially Monte Carlo simulations—can give a false sense of confidence if misunderstood. He explains what these tools actually measure, the hidden assumptions behind them, and why retirement is a complex problem that requires judgment, flexibility, and resilience—not just a high “success rate.” Roger shares how to properly interpret results, avoid common traps, and use software as a guide rather than a decision-maker so you can build

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61:09

Retirement Talk with Dr. Wade Pfau

Retirement Answer Man ·

2026/03/18

💬 Show NotesWade 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

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50:27

Healthcare Before Medicare: Retiree Feedback

Retirement Answer Man ·

2026/03/11

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.OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN(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

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67:51

How to Feel Loved with Dr. Harry Reis

Retirement Answer Man ·

2026/03/04

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.OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN(00:00) This show is dedicated to helping

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45:56

Healthcare Before Medicare: Creating Your Own Action...

Retirement Answer Man ·

2026/02/25

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

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52:46

Healthcare Before Medicare: How to Lower Your Costs

Retirement Answer Man ·

2026/02/18

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

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44:53

Healthcare Before Medicare: Your Options

Retirement Answer Man ·

2026/02/11

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN(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.PRACTICAL PLANNING SEGMENT(05:05) After last week’s sticker shock, Roger

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42:25

Healthcare Before Medicare: What Happens When You...

Retirement Answer Man ·

2026/02/04

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.OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN(00:00) This show is

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28:22

Retire on FIRE: Rocking an Early Retirement- The...

Retirement Answer Man ·

2026/01/28

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.OUTLINE OF THIS EPISODE OF THE

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47:45

Retire on FIRE: Rocking an Early Retirement- Henry...

Retirement Answer Man ·

2026/01/21

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.OUTLINE OF THIS

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53:53

Retire on Fire- Rocking an Early Retirement: Henry...

Retirement Answer Man ·

2026/01/14

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.OUTLINE OF

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49:56

Retire on FIRE- Rocking an Early Retirement: Meet...

Retirement Answer Man ·

2026/01/07

As the new year begins, Roger Whitney launches a new Retirement Plan Live case study, introducing Henry and Lucy, a couple in their mid-40s pursuing Financial Independence and Retire Early (FIRE). Roger revisits the 4% rule as a planning heuristic, explains when it can be helpful, and sets the stage for a live community analysis later this month. The episode closes with a Smart Sprint focused on updating your net worth statement and a listener’s word for 2026.OUTLINE OF THIS EPISODE OF THE

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37:44

Year-End Planning: Estimated Tax Payments

Retirement Answer Man ·

2025/12/31

As the year comes to a close, Roger Whitney reflects on the power of words, walks through an important year-end tax planning reminder for retirees, shares listener stories and perspectives, and invites listeners to choose a guiding word for 2026 as a way to approach retirement with greater intention and clarity.OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN(00:00) This show is dedicated to helping you not just survive retirement, but have the confidence and clarity to lean in and rock

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46:24

Year-End Planning: The Basics of Charitable Giving

Retirement Answer Man ·

2025/12/24

In this Christmas Eve episode, Roger Whitney explores the basics of charitable giving as part of an intentional retirement plan, with a timely focus on year-end decisions. He explains how charitable deductions work, common planning mistakes to avoid, and why generosity is most effective when paired with a resilient financial plan. Roger also shares a Rocking Retirement in the Wild story from a listener who is actively living a purpose-filled retirement, reflects on the corporate language we

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40:11

Year End Planning: RMD Rules for IRAs & Inherited IRAs

Retirement Answer Man ·

2025/12/17

In this episode, Roger Whitney walks listeners through the complexities of inherited IRAs, highlighting the impact of the SECURE Act of 2019 and clarifying the distinctions between eligible and non-eligible designated beneficiaries. He explains how these classifications affect withdrawals and tax planning, making the rules easy to understand. Roger also answers listener questions on topics like retirement team selection and funding health insurance with HSA accounts. Beyond the numbers, he

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41:10

Year-End Planning: Annual Gifting Rules

Retirement Answer Man ·

2025/12/10

In this episode, Roger Whitney, a retirement planner with 30 years of experience, breaks down annual gifting limits and year-end planning. He shares practical strategies for giving that make a real impact and create meaningful experiences for loved ones. Roger also answers listener questions, providing clear guidance to help you navigate your retirement with confidence.OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN(00:00) This podcast is dedicated to helping you rock

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36:36

Year-End Planning: Tax-Loss Harvesting

Retirement Answer Man ·

2025/12/03

💬 Show NotesIn this episode, Roger Whitney kicks off a month-long series on year-end planning for retirement. He shares insights on tax loss harvesting, a technique that can help you minimize capital gains tax. Listen in as Roger explains the basics of capital gains, the importance of proactive planning, and the potential benefits of offsetting gains with losses. Plus, he introduces a smart sprint action item to help you optimize your tax strategy before the year's end!OUTLINE OF THIS

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38:07

Should I Use My Traditional IRA to Fund My Life or Do...

Retirement Answer Man ·

2025/11/26

💬 Show NotesIn this Thanksgiving Eve episode, Roger Whitney encourages listeners to carry gratitude into everyday life, emphasizing the value of recognizing specific moments and taking “mental snapshots” of what matters. He also addresses common retirement questions, including how to think about traditional versus Roth IRAs and whether to use IRA withdrawals or pursue Roth conversions. It’s a clear, practical discussion to help you reflect and make informed planning decisions.OUTLINE OF

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665 results

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