PODCAST · business
Retirement Answer Man
by 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 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
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Year-End Planning Checklist for Retirees
Episode Overview Year-end planning doesn't have to become a giant project. Roger walks through the key items every retiree should put eyes on before December 31st -- not to do everything, but to avoid the unforced errors that sneak up on you. He also takes listener questions on coordinating…
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The Perfect Portfolio with Peter Lazaroff
Peter Lazaroff, Chief Investment Officer of PlanCorp and author of The Perfect Portfolio, joins Roger to explore what makes a portfolio “perfect.” The answer isn’t a mathematically optimized portfolio—it’s one that serves your life. They discuss how to align investments with your goals and…
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Your Social Security Playbook: Building Your Strategy- Married Filers
Roger Whitney closes out his five-week Social Security series with a practical framework for married couples deciding when to claim. He explains how to coordinate benefits, avoid common mistakes, and make a decision that fits the household rather than relying on a single calculator or searching…
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Your Social Security Playbook: Building Your Strategy- Single Filers
Roger Whitney explains how solo filers can make a confident Social Security claiming decision without getting overwhelmed by complexity. He covers the biggest mistakes to avoid, introduces a practical decision-making framework, answers listener questions about survivor benefits, and closes with a...
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Your Social Security Playbook: The Levers You Control
Roger Whitney explains six levers that can influence Social Security benefits: reviewing your earnings record, choosing when to claim, managing retirement income, reconsidering an early claim, considering where you live, and coordinating spousal or survivor benefits. The episode emphasizes that…
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Your Social Security Playbook: How Your Benefit is Calculated
How is your Social Security benefit actually calculated? In this episode, Roger explains how you qualify for retirement benefits, how your earnings history determines your benefit, and why the age you claim matters. Understanding these basics will help you recognize the areas where you have…
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Your Social Security Playbook: How the System Works
Social Security is one of the most important pieces of a retirement plan, but how does the system work, and will it remain financially viable for future retirees? Roger begins a five-week series on building your Social Security playbook by exploring the program’s history, funding structure, and...
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Summer Reruns: Learn What to Ignore with Dr. Daniel Crosby
In this summer replay, Roger talks with Dr. Daniel Crosby about learning what to ignore in an age of information overload. They explore how to filter financial advice, align decisions with your values, and focus your attention on what truly matters to your finances and your life. OUTLINE OF THIS...
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Summer Reruns: Gabbing with Gretchen Rubin- Your Personality and How it Plays into Your Retirement Planning
This Summer Replay revisits Roger’s 2018 conversation with Gretchen Rubin about the Four Tendencies and how understanding your personality can help you create a retirement plan and daily life that truly fit who you are. OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN (00:00) Roger introduces...
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Summer Reruns: Keep Investments Simple with Peter Lazaroff
As part of Roger’s summer replay series, he revisits a conversation with Peter Lazaroff about the value of elegant simplicity in retirement investing. They discuss why more sophisticated strategies are not necessarily better, how added complexity can create unexpected risks, and why the money...
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Summer Reruns: Retiring Single with Tanya Nichols
August is encore month on the Retirement Answer Man podcast, giving Roger an opportunity to step back, reflect, and revisit some of the show's most impactful conversations. This week, he replays his discussion with Tanya Nichols on retiring single—a topic that remains just as relevant today....
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Retirement Toolkit: Never Worry About Money Again with Jesse Mecham
What if budgeting wasn't about restriction, but about giving every dollar a purpose? This week, Roger sits down with Jesse Mecham, founder of YNAB (You Need A Budget), to discuss the power of intentionality with money. Together, they explore how asking one simple question, "What is this money…
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Retirement Toolkit: How do you Balance Optimization with Simplification
How do you know when it's worth optimizing your retirement plan and when it's better to keep things simple? This week, Roger answers a listener question by exploring Aristotle's concept of the "golden mean," arguing that the best retirement decisions are rarely found at either extreme. He…
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Retirement Toolkit: How to Rebalance a Retirement Portfolio
This week Roger explains why rebalancing is one of the most important disciplines in retirement planning. In the Retirement Toolkit, he explores the difference between a traditional investment allocation and a retirement allocation, explaining how to organize your assets to support both your...
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Retirement Toolkit: How Does Step Up in Cost Basis Work
This week Roger talks about one of the biggest challenges retirees face today: information overload. He explains why more information doesn't always lead to better decisions and why building a great retirement starts with focusing on what matters most to you. In the Retirement Toolkit, Roger...
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Retirement Toolkit: How Required Minimum Distributions (RMDs) Work
This week Roger explores the idea of "digging where your feet are" and how focusing on what you can do today can reduce anxiety about the future and regret about the past. In the Retirement Toolkit, he explains the basics of Required Minimum Distributions (RMDs), including when they begin, which...
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IRMAA: The Medicare Premium Surprise and How to Avoid It
This week Roger breaks down IRMAA Medicare surcharges and why retirees should understand them without letting them dominate retirement planning decisions. He explains how the income thresholds work, common planning mistakes to avoid, and what happens if you cross into a higher premium bracket....
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Mutual Funds vs. ETFs- Which is Better for Retirement?
This week, a simple quote about wasting time sparks a deeper conversation about why retirement isn't meant to be endlessly optimized. In the Retirement Toolbox, we compare mutual funds and ETFs, exploring their differences in costs, trading, and tax efficiency. Listener questions cover Roth...
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Know What You Pay: A Guide to Investment & Advice Costs
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…
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Take the Retirement Leap of Faith with Jordan Grumet
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....
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Decluttering for Retirement: Your Step-by-Step Plan
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…
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Decluttering for Retirement: Why It's So Hard and How to Push Through
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...
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Decluttering for Retirement: How a Simpler Life Helps You Rock Retirement
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...
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Decluttering for Retirement: It's More Than Cleaning Out Your Closet
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...
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How Long Will You Live After Retirement?
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...
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Listener Questions: How Do I Create a Diversified Portfolio?
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.…
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Listener Questions: What Should I Be Doing When I'm Two Years from Retirement?
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…
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Listener Questions: Should I Take Social Security Early and Invest It?
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…
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Listener Questions: Should I Move My 401K into an IRA When I Retire?
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....
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Why Even the Best Retirement Calculator is Wrong
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,...
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Retirement Talk with Dr. Wade Pfau
💬 Show Notes 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...
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Healthcare Before Medicare: Retiree Feedback
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....
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How to Feel Loved with Dr. Harry Reis
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...
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Healthcare Before Medicare: Creating Your Own Action Plan
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...
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Healthcare Before Medicare: How to Lower Your Costs
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...
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Healthcare Before Medicare: Your Options
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…
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Healthcare Before Medicare: What Happens When You Retire Before 65?
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...
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Retire on FIRE: Rocking an Early Retirement- The Challenges of Retiring Early
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...
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Retire on FIRE: Rocking an Early Retirement- Henry and Lucy's Resources
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…
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Retire on Fire- Rocking an Early Retirement: Henry and Lucy's FIRE Goals
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…
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Retire on FIRE- Rocking an Early Retirement: Meet Henry and Lucy
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...
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Year-End Planning: Estimated Tax Payments
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...
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Year-End Planning: The Basics of Charitable Giving
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…
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Year End Planning: RMD Rules for IRAs & Inherited IRAs
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...
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Year-End Planning: Annual Gifting Rules
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,...
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Year-End Planning: Tax-Loss Harvesting
💬 Show Notes In 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...
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Should I Use My Traditional IRA to Fund My Life or Do Roth Conversions?
💬 Show Notes In 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…
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My Advisor Recommended an Annuity. Should I Buy It?
💬 Show Notes In 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...
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How Do I Build My Initial Cash Cushion for Retirement?
💬 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...
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The 10 R's for a Joyful Retirement with Cesar Aguirre
💬 SHOW NOTES 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…
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ABOUT THIS SHOW
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
HOSTED BY
Roger Whitney, CFP®, CIMA®, RMA, CPWA®
CATEGORIES
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Frequently Asked Questions
How many episodes does Retirement Answer Man have?
Retirement Answer Man currently has 670 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.
What is Retirement Answer Man about?
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...
How often does Retirement Answer Man release new episodes?
Retirement Answer Man releases new episodes frequently with a large back catalog of 670 episodes. Check the episode list for recent publication dates.
Where can I listen to Retirement Answer Man?
You can listen to Retirement Answer Man on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.
Who hosts Retirement Answer Man?
Retirement Answer Man is created and hosted by Roger Whitney, CFP®, CIMA®, RMA, CPWA®.
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