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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

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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35:50

My Advisor Recommended an Annuity. Should I Buy It?

Retirement Answer Man ·

2025/11/19

💬 Show NotesIn this episode, Roger Whitney dives into the essentials of required minimum distributions, explaining the age thresholds, how the amounts are calculated using IRS life expectancy tables, and how to manage multiple IRAs and 401(k)s. He also answers listener questions, including whether a flexible premium deferred income annuity might make sense and how to determine how much you can safely give to loved ones or charity now. Packed with practical advice and actionable insights,

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38:35

How Do I Build My Initial Cash Cushion for Retirement?

Retirement Answer Man ·

2025/11/12

💬 Show NotesIn 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 insightful discussion designed to help you confidently navigate and optimize

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46:05

The 10 R's for a Joyful Retirement with Cesar Aguirre

Retirement Answer Man ·

2025/11/05

💬 SHOW NOTESIn 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 addresses listener questions on planning, discretionary spending, and

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51:36

Retirement Goal Case Study

Retirement Answer Man ·

2025/10/29

💬 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 planning. Tune in for insights that will help you make your retirement not

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55:36

How to Navigate Goals as Life Unfolds

Retirement Answer Man ·

2025/10/22

💬 Show NotesIn 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 align your retirement goals with your evolving self and make informed

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45:42

Building Agile Retirement Goals

Retirement Answer Man ·

2025/10/15

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 retirement. Tune in to learn how to navigate your retirement journey

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32:02

Setting Retirement Goals: The Paradox of Knowing What...

Retirement Answer Man ·

2025/10/08

💬 Show NotesIn 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 the pitfalls of external scripts and societal expectations.OUTLINE OF

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59:26

Simple Isn't Easy: Carl Richards on Life and Retirement

Retirement Answer Man ·

2025/10/01

SHOW NOTESIn 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 RETIREMENT ANSWER MAN(00:00) The ultimate goal in building a retirement plan

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35:01

The Difference Between an IRS Late Payment Penalty...

Retirement Answer Man ·

2025/09/24

SHOW NOTESIn 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 your retirement!OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN(00:00)

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38:00

How to Read Your Social Security Statement

Retirement Answer Man ·

2025/09/17

💬 SHOW NOTESIn 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 chapter in life.OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER

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49:17

Don't Get Cute with Your Retirement Investments

Retirement Answer Man ·

2025/09/10

💬 Show NotesIn 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 investment strategies—highlighting when they might help, and when they

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41:23

Navigating Medicare in 2025

Retirement Answer Man ·

2025/09/03

💬 Show NotesIn 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 valuable insights and practical tips to ensure you make the best choices

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40:18

Should I Do a "Free" Retirement Analysis?

Retirement Answer Man ·

2025/08/27

💬 SHOW NOTESIn 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 potential costs and consequences involved. Tune in for insightful advice on

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45:47

Direct Indexing vs. Mutual Fund or ETFs

Retirement Answer Man ·

2025/08/20

💬 Show NotesIn 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 confidence and control.OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER

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51:37

Elder Care Options for Singles

Retirement Answer Man ·

2025/08/13

💬 Show NotesIn 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 practical insights on guardianships and conservatorships, Roger shares a

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36:24

How to Choose a Retirement Coach

Retirement Answer Man ·

2025/08/06

💬 Show NotesIn 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 insights to help you navigate your retirement journey!OUTLINE OF THIS

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35:37

Replay: How to Manage Your Scarcity Brain

Retirement Answer Man ·

2025/07/30

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 modern abundance. Tune in for insights that can help you not just

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28:36

Replay: Overcoming Frugality in Retirement with Dr....

Retirement Answer Man ·

2025/07/23

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. Discover practical strategies to gain confidence in spending, overcome the

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