Retirement Answer Man

Retirement Answer Man

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 financial number. It’s finding that balance between living well today and feeling confident about your retirement. It’s about gaining more freedom to pursue the life you want. Join the rock retirement community at www.rogerwhitney.com

Episodes

November 12, 2025 38 mins

💬 Show Notes


In this episode, Roger Whitney explores the psychology of loss aversion and how it affects financial decision-making. He introduces the new Retirement Toolbox segment, offering practical, actionable tools to help you strengthen your retirement plan. We also cover the benefits of Qualified Charitable Distributions and answer listener questions on retirement planning and asset allocation. Don’t miss this ins...

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In this episode, Roger Whitney explores the art of retirement goal setting with his signature blend of practical advice and thoughtful reflection. He sits down with Cesar Aguirre, who shares how leaving a corporate career led to a purposeful and fulfilling retirement, the evolution of his book, and the importance of aligning goals with personal values rather than just chasing big achievements. Roger also a...

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October 29, 2025 51 mins

💬 Show Notes


 In this episode, Roger Whitney wraps up our four-week series on smarter retirement goal setting. He dives into the ideas of buoyancy and Maslow’s hierarchy of needs, showing how they play a role in planning a retirement that actually works for you. Using two relatable avatars – the Grinder and the Dreamer – Roger shares practical, real-world strategies to help navigate the twists and turns of retirement p...

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October 22, 2025 55 mins

💬 Show Notes


In this episode, we continue our four-week series on better retirement goal setting with Roger Whitney. This week, we delve into the dynamics of navigating retirement goals as life unfolds and the concept of opportunity cost. In the second half, Roger has enlightening discussion with Dr. Bobby, where he explores the pros and cons of organic food and its relevance to our health and finances. Discover how to...

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October 15, 2025 45 mins

In this episode, Roger Whitney continues his four-week series on retirement goal setting, focusing on the importance of building agile retirement goals. He emphasizes creating the right conditions for discovering what you truly want in retirement, rather than fixating on specific desires. Roger shares insights on self-discovery, the anatomy of goals, and the significance of establishing a solid foundation for a fulfilling ...

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In this episode, Roger Whitney kicks off a four-week series on retirement goal setting, tackling the paradox of knowing what you want in retirement. He discusses the challenges of articulating desires for a life stage that many have never experienced, emphasizing the importance of not oversimplifying retirement goals. Tune in to explore how to set the right conditions for a fulfilling retirement and avoid ...

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In this episode, Roger Whitney sits down with Carl Richards, a financial advisor-turned-artist, to talk about keeping retirement planning simple and meaningful. They dive into the idea of “elegant simplicity,” the importance of knowing your goals, and making decisions that actually work for you. Plus, hear inspiring stories from club members to help you rock your retirement!


OUTLINE OF THIS EPISODE OF THE ...

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In this episode, we tackle the often-overlooked topic of taxes in retirement with expert Erin Coe, an enrolled agent. Discover how to avoid unexpected penalties and interest on your IRA distributions and Roth conversions. We also share an inspiring retirement success story from Lottie, reminding us of the importance of clarity and simplicity in planning. Tune in for practical advice that will help you rock yo...

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September 17, 2025 38 mins

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In this episode, we focus on empowering you to navigate retirement with confidence. We break down the process of reading a Social Security statement, examining each section and its significance. Additionally, we tackle listener questions regarding retirement strategies, second mortgages, and Roth conversions. Join us for practical insights that will help you make informed decisions as you approach this new...

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In this episode of the Retirement Answer Man, Roger Whitney sits down with Peter Lazaroff, Chief Investment Officer at Plancorp, for a thoughtful conversation on the power of simplicity in retirement planning. Together, they unpack the common traps of overcomplicating investments and the cognitive biases that often lead us astray. Peter also offers valuable insights into private equity and other complex in...

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September 3, 2025 41 mins

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In this episode, we explore the intricacies of navigating Medicare in 2025 with Medicare expert Danielle Roberts from Boomer Benefits. Discover the recent changes in Medicare Advantage and Part D plans that could impact your healthcare decisions. We also share inspiring stories of individuals embracing life in retirement and discuss the importance of reviewing your Medicare options annually. Tune in for va...

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In this episode, we explore the implications of the saying 'nothing is for free' in the context of retirement planning. Join Roger Whitney, a seasoned retirement planner, as he shares a heartfelt story from a listener, David, who exemplifies the spirit of 'rocking retirement.' Additionally, Roger tackles the critical question of whether to accept a free retirement analysis from brokers, discussing the pote...

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August 20, 2025 45 mins

💬 Show Notes


In this episode, Roger explores how naming and recognizing the different phases of life can bring clarity to the retirement journey. A listener’s question about inherited money sparks a conversation about direct indexing—what it is, when it makes sense, and what to watch out for. He also shares how to navigate calm, choppy, and rough waters in retirement planning so listeners can move forward with more con...

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August 13, 2025 51 mins

💬 Show Notes


In this episode, Roger Whitney welcomes elder law expert Kathy McNair to discuss the often-overlooked but crucial topic of elder care, especially for those retiring solo. They explore what elder law really means, how it differs from traditional estate planning, and why having the right legal documents—like healthcare proxies and powers of attorney—is vital for protecting your future and legacy. Alongside p...

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August 6, 2025 36 mins

💬 Show Notes


In this episode, Roger Whitney returns after a month off, ready to help you rock your retirement! He answers listener questions on a range of topics, including the benefits of choosing between Fidelity and Vanguard, the Rule of 55 for 401(k) withdrawals, and inherited IRA distributions. Roger also chats with  discusses the importance of finding the right retirement coach. Join us for practical advice and i...

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In this episode, Roger Whitney welcomes Michael Easter, New York Times bestselling author of 'The Comfort Crisis' and 'Scarcity Brain.' They delve into the concept of overcoming frugality and the evolutionary mismatches that affect our resource management in retirement. Discover how short-term discomfort can lead to long-term growth, the importance of taking the stairs in life, and the psychological implications of our mod...

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In this enlightening episode, we tackle the often overlooked mental shift required in retirement: transitioning from a saver to a spender. Join us as we revisit a compelling conversation with Dr. Daniel Crosby, Chief Behavioral Officer at Orion Advisory Services. We'll explore the psychological barriers many face in letting go of frugality and how to embrace the resources they've accumulated to enhance their lives. Dis...

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In this episode, we explore the journey of retirement through the eyes of Brad, a member of the Rock Retirement Club. Brad shares his experience of moving to The Villages in Florida, detailing his decision-making process, the community's offerings, and how it has transformed his retirement lifestyle. Join us as we uncover valuable insights and tips for anyone considering retirement living, all while enjoying the vibrant at...

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All of July we will be replaying some of our popular past episodes. In this episode, we engage with retirement planning expert Michael Kitces as we explore the evolving landscape of retirement planning. Discover the importance of flexibility in retirement spending and how to select the right retirement planner for your needs. We also discuss the implications of dying with too much money and the critical questions you s...

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All July long, we’re featuring a special replay series of standout episodes—and this week is no exception.

Join us for a special episode as we welcome Christine Benz to discuss her book, "How to Retire." In a captivating conversation in the Rock Retirement Club, we dive into topics like long-term care, the 4% rule, investing strategies, and simplification. Featuring insights from Fritz Gilbert, a member of the club ...

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