Retirement Answer Man
Business & Finance
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 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
- 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…
- 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…
- 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 w…
- 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…
- 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 info…
- 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 in…
- 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,…
- 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 re…
- 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. Wa…
- 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 withdraw…
- 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 belon…
- 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 confid…
- 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…
- 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…
- 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…
- 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, an…
- 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…
- 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…
- 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…
- 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 fo…
- 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 mistake…
- 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 exp…
- 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…
- 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 explain…
- 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 addresse…
- 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 4…
- 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 strength…
- 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…
- Retirement Goal Case Study
💬 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…
- How to Navigate Goals as Life Unfolds
💬 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.…
- Building Agile Retirement Goals
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 ret…
- Setting Retirement Goals: The Paradox of Knowing What You Want
💬 Show Notes 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 ma…
- Simple Isn't Easy: Carl Richards on Life and Retirement
SHOW NOTES 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…
- The Difference Between an IRS Late Payment Penalty and Interest
SHOW NOTES 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 als…
- How to Read Your Social Security Statement
💬 SHOW NOTES 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 listen…
- Don't Get Cute with Your Retirement Investments
💬 Show Notes 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…
- Navigating Medicare in 2025
💬 Show Notes 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…
- Should I Do a "Free" Retirement Analysis?
💬 SHOW NOTES 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,…
- Direct Indexing vs. Mutual Fund or ETFs
💬 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…
- Elder Care Options for Singles
In this episode, Roger Whitney speaks with elder law expert Kathy McNair about crucial elder care considerations for individuals retiring alone. They cover the distinctions between elder law and estate planning, the importance of legal doc…
- How to Choose a Retirement Coach
Roger Whitney discusses how to select a retirement coach, detailing the qualities to look for and the differences between an advisor and a coach. The episode also addresses listener inquiries regarding Fidelity and Vanguard accounts, the R…
- Replay: How to Manage Your Scarcity Brain
Roger Whitney interviews Michael Easter, author of "Scarcity Brain," to discuss managing a "scarcity brain" and overcoming frugality. They explore evolutionary mismatches affecting resource management and how embracing short-term discomfor…
- Replay: Overcoming Frugality in Retirement with Dr. Dan Crosby
This replay episode of Retirement Answer Man features Dr. Daniel Crosby discussing the psychological challenges of transitioning from a saver to a spender in retirement. The discussion includes strategies for gaining confidence in spending…
- Replay: My Experience Moving to a Retirement Community
Brad discusses his experience moving to The Villages retirement community in Florida, detailing his decision-making process and how the community has impacted his retirement lifestyle. The episode offers insights for those considering reti…
- Replay: The State of Retirement Planning with Michael Kitces
This episode features retirement planning expert Michael Kitces discussing the evolving landscape of retirement planning. Key topics include the importance of flexible retirement spending, how to select a retirement planner, and the implic…
- Replay: How to Retire with Christine Benz
This episode features a replay of an interview with Christine Benz about her book "How to Retire." The discussion covers financial and non-financial aspects of retirement planning, including long-term care, the 4% rule, investing strategie…
- I Just Lost My Job. Can I Retire Now?
This episode of Retirement Answer Man explores the possibility of early retirement for a listener who lost their job, analyzing their financial situation and simulating various scenarios. It also features listener stories of successful ret…
- How to Quality Check Your Retirement Plan
This episode of Retirement Answer Man discusses quality checking retirement plans through concepts like "productive paranoia" and metacognition, while also sharing Scott's international travel experiences post-life change.
- How to Rebalance Your Portfolio in Retirement
This episode of Retirement Answer Man covers rebalancing a retirement portfolio with Roger Whitney. It details six steps for rebalancing, including reviewing spending, updating income estimates, and assessing plan resilience, alongside lis…
- How to Improve Your Retirement Travel
This episode of The Retirement Answer Man discusses improving travel in retirement, exploring motivations and obstacles. It features insights from Andrew Motiwala, founder of A Good Life Abroad, about living abroad and the advantages of th…