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Retirement Answer Man

Retirement Answer Man

Roger Whitney, CFP®, CIMA®, RMA, CPWA® 653 episodes Latest Jun 10, 2026

A top retirement podcast hosted by Roger Whitney, a certified financial planner. It covers both financial and personal aspects of retirement, including creating a paycheck, Medicare, Social Security, tax management, and non-financial topics like travel. The podcast aims to help listeners retire with confidence and find balance between living well today and feeling secure about the future.

Episodes

Know What You Pay: A Guide to Investment & Advice Costs Jun 10, 2026 2516 Roger Whitney explores the relationship between cost and value in retirement planning, focusing on how to better understand the fees associated with financial advice, investments, and insurance products. Using a listener question about an annuity recommendation as a starting point, he explains why investors need clarity around what they are paying so they can determine whether they are re
Take the Retirement Leap of Faith with Jordan Grumet Jun 3, 2026 3536 Roger Whitney explores the idea that retirement always involves both excitement and uncertainty. While people spend years gathering information, running projections, and refining plans, there comes a point when no amount of additional analysis can eliminate risk. Through a conversation with Dr. Jordan Grumet, Roger discusses why retirement ultimately requires a leap of faith, how fear of
Decluttering for Retirement: Your Step-by-Step Plan May 27, 2026 3663 In this episode, retirement expert Roger Whitney and Marie Kondo consultant Dr. Lindsey Hardegree explore the transformative power of decluttering. They discuss how clearing physical and emotional clutter can pave the way for a joyful and intentional retirement. Lindsey shares practical strategies from the Konmari method, focusing on identifying what truly sparks joy and letting go of the
Decluttering for Retirement: Why It's So Hard and How to Push Through May 20, 2026 2674 Roger Whitney continues the decluttering series by focusing on the hidden challenges that keep people stuck. Rather than treating decluttering as a massive life overhaul, he explains how perfectionism, emotional attachment, deferred decisions, and fear of change can quietly create friction across our belongings, finances, and relationships. The episode also tackles listener questions on m
Decluttering for Retirement: How a Simpler Life Helps You Rock Retirement May 13, 2026 2356 Roger Whitney continues the decluttering series by exploring the opportunities that come from simplifying your life, finances, and relationships. He explains how reducing complexity can create more mental space, clarity, and confidence in retirement while also making it easier to focus on what matters most. Along the way, Roger dives into the origins and limitations of risk tolerance ques
Decluttering for Retirement: It's More Than Cleaning Out Your Closet May 6, 2026 3019 Roger Whitney kicks off a new series on decluttering for retirement, explaining how the accumulation of “stuff”—from physical belongings to financial accounts to relationships—can unconsciously shape our decisions and limit our ability to envision a fulfilling next chapter. He reframes retirement as a rare opportunity to reset your identity, let go of what no longer serves you, and intent
How Long Will You Live After Retirement? Apr 29, 2026 3468 Roger Whitney explores one of the most overlooked variables in retirement planning: longevity, and how assuming you’ll live too long can quietly force you to save more, spend less, and potentially miss out on life. Through a conversation with Dr. Bobby Du Bois, he challenges default planning assumptions, walks through the real trade-offs, and introduces a practical way to think about life
Listener Questions: How Do I Create a Diversified Portfolio? Apr 22, 2026 2886 Roger Whitney breaks down how to create a diversified portfolio by explaining the core principles of diversification and asset allocation, then answers listener questions on topics like using allocation funds, shifting from the S&P 500 to total market funds, and strategies like buy, borrow, die. He emphasizes that while diversification reduces unnecessary risk, asset allocation is the
Listener Questions: What Should I Be Doing When I'm Two Years from Retirement? Apr 15, 2026 2876 In this episode, Roger Whitney breaks down essential elements you need to consider before and during retirement. From understanding inflation risks to strategic asset reallocation, this episode offers practical advice to help you make informed decisions and craft a retirement that aligns with your values.OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN PODCAST(00:00) Introduction and
Listener Questions: Should I Take Social Security Early and Invest It? Apr 8, 2026 2518 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 an
Listener Questions: Should I Move My 401K into an IRA When I Retire? Apr 1, 2026 2570 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 com
Why Even the Best Retirement Calculator is Wrong Mar 25, 2026 3572 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

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