Podcast
Retirement Answer Man
Hosted by Roger Whitney, CFP®, CIMA®, RMA, CPWA® · EN
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
27episodes
Episodes
Newest firstAll episodes
Decluttering for Retirement: Why It's So Hard and How to Push Through
2d ago00:44:34Tap to summarizeRoger 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 market uncertainty, international investing, gray divorce, healthcare options like MediShare versus ACA plans, and longevity planning. It closes with an inspiring Rockin’ Retirement in the Wild update from Beth, who shares how intentionally redesigning her life after burnout created a simpler and more fulfilling retirement.OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN(00:00) Roger previews the episode, shares details about the upcoming Noodle Live event, and outlines the next phase of the decluttering series.PRACTICAL PLANNING SEGMENT(02:18) Roger introduces one of the biggest challenges of decluttering: making the process feel too overwhelming and believing it has to be done perfectly. (04:20) Roger explains why clutter often persists because it lacks urgency and people wait for a triggering event before taking action.(06:57) He explores the emotional and practical obstacles tied to physical possessions, including memories, unfinished projects, family heirlooms, and sunk costs.(10:34) Roger breaks down financial clutter and why accounts, relationships, taxes, and uncertainty can make simplification feel risky.(11:52) He discusses relationship clutter, including obligations, organizations, unhealthy dynamics, and the fear of disappointing others.(14:20) How do we overcome these challenges?LISTENER QUESTIONS(15:17) Roger answers a question about whether global sentiment toward U.S. leadership should impact international versus domestic investment allocation decisions.(24:43) A listener facing gray divorce asks for guidance, leading Roger to discuss grief, rebuilding identity, and creating a new vision for retirement.(29:05) Roger shares his experience using MediShare and discusses important healthcare considerations before choosing alternatives to ACA coverage.(33:13) Roger responds to listener feedback on longevity planning and balancing the risk of overspending versus running out of money.ROCKIN’ RETIREMENT IN THE WILD(35:24) Beth shares an update on her retirement transformation after leaving a stressful healthcare career and intentionally creating a simpler life centered around flexibility, joy, and financial sustainability.SMART SPRINT(42:17) Identify the challenges you may face in decluttering your things, finances, or relationships and jot down one possible strategy to overcome each obstacle.REFERENCESlivewithroger.com — Register for Noodle Live on June 18!Submit a Question for RogerSign up for The NoodleNote: The opinions expressed are for informational purposes only and should not replace personalized advice from licensed professionals.
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Decluttering for Retirement: How a Simpler Life Helps You Rock Retirement
1w ago00:39:16Tap to summarizeRoger 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 questionnaires, discusses how retirees can structure portfolios around purpose rather than arbitrary scores, and answers listener questions on donor-advised funds and Social Security survivor benefits. The episode wraps with practical reflections on decluttering digital inputs and defining your personal motivation for simplifying your life.OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN(00:00) Roger explains how decluttering helps reclaim your attention in a world competing for your focus.(01:37) Roger previews week two of the decluttering series and introduces the themes of opportunity, risk tolerance, and listener questions.ROCKIN’ RETIREMENT IN THE WILD(02:07) Rick shares how he’s enjoyed five years of retirement without feeling pressure to chase a larger “purpose,” instead embracing freedom, reading, and travel after leaving behind a stressful corporate career.RETIREMENT TOOLKIT(03:30) Roger responds to a listener's question about how risk tolerance should fit into a three-bucket retirement strategy. (11:15) He outlines why retirement planning should focus on building allocations from the ground up based on purpose and time horizon.PRACTICAL PLANNING SEGMENT(18:03) Roger explores the opportunities created by decluttering your things, including reducing overwhelm, maintenance, and future burdens on loved ones.(20:53) He discusses how simplifying finances can increase clarity, reduce anxiety, and create greater confidence in retirement.(24:25) Roger explains how decluttering relationships and obligations can create space for more intentional connections.(25:33) He highlights the importance of reducing digital and news clutter to protect your attention and mental bandwidth.LISTENER QUESTIONS(28:28) Roger explains how donor-advised funds can help simplify a cluttered brokerage account while improving tax efficiency for charitable giving.(33:00) He answers a widower’s question about Social Security survivor benefits, timing strategies, and earnings test considerations.SMART SPRINT(36:00) Write down four or five benefits you hope to gain from decluttering your things, finances, relationships, or digital life to help stay motivated through the process.CLOSING THOUGHTS(38:20) Roger congratulates our podcast editor, Graham, on graduating from Baylor University.REFERENCESSubmit a Question for RogerSign up for The NoodleNote: The opinions expressed are for informational purposes only and should not replace personalized advice from licensed professionals.
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Decluttering for Retirement: It's More Than Cleaning Out Your Closet
2w ago00:50:19Tap to summarizeRoger 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 intentionally design a life aligned with who you want to become. The episode wraps with listener questions across a variety of retirement planning topics, including follow-ups on last week’s discussion around longevity. OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN(00:00) Roger introduces retirement as a “refresh” moment and explains why decluttering is essential to stepping into a new identity. (01:11) Roger outlines the month-long decluttering series and introduces the three key domains: things, money, and relationships.ROCKIN’ RETIREMENT IN THE WILD(3:43) Will realized that selling his BMW wasn’t about the car, but about letting go of a past version of himself and it inspired him to keep decluttering. PRACTICAL PLANNING SEGMENT(05:13) Roger defines the core problem of clutter, explaining how accumulated decisions create overwhelm and limit future possibilities.(07:42) Roger explores physical clutter and how decades of possessions tied to past life stages can prevent you from envisioning a new lifestyle.(13:32) He breaks down financial clutter, including scattered accounts and legacy investments, and why simplification becomes critical in retirement.(17:26) Roger discusses relationship and obligation clutter, emphasizing the need to be intentional about who and what you invest your time in.LISTENER QUESTIONS(22:20) A widow shares her experience navigating longevity risk and loss, prompting a discussion on planning flexibility, spending, and building a support network.(29:33) Roger responds to a listener’s approach to modeling longevity scenarios and explains how to use projections to inform better life decisions rather than just optimize numbers.(35:30) He evaluates whether an annuity recommendation actually solves a meaningful problem or simply adds complexity.(41:30) Roger discusses the trade-offs between saving more versus using existing cash, highlighting flexibility and optionality in retirement planning.SMART SPRINT(46:07) Spend time this week identifying areas of clutter in your things, money, and relationships and simply observe what may no longer be serving you.CLOSING THOUGHTS(47:20) Roger reflects on listener feedback and The Noodle Live.REFERENCESSubmit a Question for RogerSign up for The NoodleNote: The opinions expressed are for informational purposes only and should not replace personalized advice from licensed professionals.
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How Long Will You Live After Retirement?
3w ago00:57:48Tap to summarizeRoger 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 lifespan so you can better align your money with how you actually want to live.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 confidence to lean in and rock it.(01:13) Roger introduces the idea that we plan heavily for running out of money but rarely consider the probability of running out of life.(02:04) Roger recognizes everyone who reached out about Sherlock’s passing and plays an audio message from a listener.ROCKING RETIREMENT IN THE WILD(03:50) Jerry shares how returning to backpacking in retirement helped him reconnect with friends and stay physically and mentally engaged.PRACTICAL PLANNING SEGMENT WITH DR. BOBBY(05:50) Roger and Dr. Bobby explore why longevity assumptions are often flawed and how they directly impact how much money you think you need.(23:54) The conversation shifts to the limits of predicting lifespan and the emotional and behavioral implications of trying to do so.(29:55) Real-life examples illustrate how longevity assumptions influence major life decisions like when to retire and how to spend your time.ROGER’S LONGEVITY FRAMEWORK(35:25) Roger introduces a practical approach to making more thoughtful longevity assumptions without overcomplicating the process.SMART SPRINT(53:10) Use a simple longevity calculator to form a baseline assumption and decide how conservative you want to be in your planning.ON THE BOOKSHELF(54:35) Roger shares what the team is reading.REFERENCESSubmit a Question for RogerSign up for The NoodleActuaries Longevity IllustratorHumans vs Retirement podcast with Dan HaylettBOOKSThe Fellowship of the Ring by J.R.R. Tolkien Alice's Adventures in Wonderland by Lewis Carroll Note: The opinions expressed are for informational purposes only and should not replace personalized advice from licensed professionals.
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Listener Questions: How Do I Create a Diversified Portfolio?
Apr 2200:48:06Tap to summarizeRoger 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 most important decision—especially in retirement, where portfolios should be structured into three buckets: contingency, liquidity, and growth—to balance stability, income needs, and long-term growth.OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN(0:00) Building wealth for retirement and investment strategies.RETIREMENT TOOLKIT(01:27) Basics of asset allocation and diversification.(02:38) Explanation of unsystematic and systematic risks.(06:26) Risk management and modern portfolio theory.(09:08) Key components and decisions in portfolio construction.(13:12) Key takeaways and practical advice.(16:10) Importance of contingency, liquidity, and growth funds.LISTENER QUESTIONS(18:20) T-Bone asks a question about asset allocation funds (26:55) An audio question about portfolio diversification(33:44) Michael asks about the ‘buy, borrow, die’ strategy (39:55) Listener shares a suggestion for what to do with a t-shirt collectionROCKING RETIREMENT IN THE WILD(40:55) Dennis shares that two years into retirement, he’s happy without a defined “purpose,” pushing back on the idea that retirement needs one.(43:22) Tim and Tammy embrace a flexible “pre-tirement” lifestyle, teaching remotely while traveling, volunteering, and exploring all 63 U.S. national parks.SMART SPRINT(45:22) Review your asset allocation and clearly define your contingency, liquidity, and growth buckets.CONCLUSION(46:09) Roger ends with a heartfelt reflection on loss and gratitude, reminding listeners to cherish meaningful moments.REFERENCESSubmit a Question for RogerSign up for The NoodleNote: The opinions expressed are for informational purposes only and should not replace personalized advice from licensed professionals.
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Listener Questions: What Should I Be Doing When I'm Two Years from Retirement?
Apr 1500:47:56Tap to summarizeIn 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 overview of upcoming topicsRETIREMENT TOOLKIT(01:49) Why inflation poses a significant risk to retirees(02:32) What is inflation and how is it measured (03:33) Causes of inflation: demand, supply constraints, and rising costs(05:20) Historical inflation rates and what they mean for your planning(06:48) How to choose a realistic inflation assumption in your plan(08:40) Strategies to hedge against inflationROCKIN RETIREMENT IN THE WILD(12:47) Jim’s story: diversity in retirement activities and the importance of adaptabilityPRACTICAL PLANNING SEGMENT(16:07) Mike’s question reframed: focus on designing your retirement life first, not account tactics(17:50) Roger reviews Mike’s facts(18:56) The importance of building a feasible plan of record, estimating expenses, and creating a realistic monthly budget for retirement(23:13) Clarifying values and how they shape your retirement goals(25:20) Income side of the plan: social security, pensions, and tax considerations(30:15) Once the plan is feasible, start testing versions of the plan and planning paycheck(31:52) 401(k) and 457 decisions can wait—focus on positioning assets for income first(33:12) Consider building after-tax savings now to increase future optionalityLISTENER QUESTIONS(35:50) Listener shares story about roadside cafe(36:20) Michael asks a question about ROTH conversions in a down market(38:50) Steve asks how to better time Roth conversions to avoid triggering IRMAA Medicare surcharges?SMART SPRINT(45:14) Smart Sprint: Before acting, ask yourself “what problem am I actually solving?”ON THE BOOKSHELF(46:25) Roger talks about his love of notebooks and shares book recommendationsREFERENCESSubmit a Question for RogerSign up for The NoodleON THE BOOKSHELFUgmonk NotebooksTheo of Golden by Allen LeviThe Three Musketeers by Alexandre DumasNote: The opinions expressed are for informational purposes only and should not replace personalized advice from licensed professionals.
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Listener Questions: Should I Take Social Security Early and Invest It?
Apr 800:41:58Tap to summarizeIn 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 and offers practical advice on managing retirement accounts and planning for the future. With insights into the psychological and financial aspects of retirement, this episode equips listeners with the knowledge to make informed decisions about their financial well-being.OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN(00:00) Introduction: Navigating retirement decisions with confidenceROCKIN’ RETIREMENT IN THE WILD(00:42) Highlighting stories of unique retirement adventures(01:08) The non-financial benefits of enjoying freedom day-by-day(04:25) Cultural pressure to plan and set goals in retirement(06:19) Retirement dreams: taking the world's longest flightPRACTICAL PLANNING SEGMENT(07:32) Addressing the dilemma: take Social Security early and invest it?(09:22) Key facts impacting Social Security claiming strategy(12:23) Investment return scenarios (14:17) Benefits of not taking SS early: market risk, guaranteed income, simplicity(19:00) Managing uncertainty and balancing investment returns(21:23) Strategies for inherited Roth IRAs and mega backdoor Roth approaches(24:40) Inheritance, aspirational goals, and resilient plans(32:03) How to avoid fees moving 401kSMART SPRINT(36:00) Smart Sprint: Download your most recent Social Security statement ON THE BOOKSHELF(37:19) Book recommendations from the teamREFERENCESSocial Security Statement – Create or access your account to view benefitsUnforgettable: The Art and Science of Creating Memorable Experiences by Phil MarshonHow the Word is Passed by Clint SmithSubmit a Question for RogerSign up for The NoodleNote: The opinions expressed are for informational purposes only and should not replace personalized advice from licensed professionals.
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Listener Questions: Should I Move My 401K into an IRA When I Retire?
Apr 100:42:50Tap to summarizeExplore 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 community questions and storiesROCKIN’ RETIREMENT IN THE WILD(01:39) A memorable travel story from Doug in Greece and the value of experiential travelRETIREMENT LIFE LAB(03:50) The significance of experiences over souvenirs for meaningful memoriesLISTENER QUESTIONS(06:15) Addressing listener questions on managing retirement accounts and consolidating assets(06:43) Handling required minimum distributions and tax considerations for late retirees (Vern's story)(09:23) Reasons to keep or roll over 401(k) assets, including inertia, access, and creditor protection(12:32) Audio question about health insurance and budgeting(18:10) Correcting misconceptions about MAGI and ACA subsidies (Michael’s feedback)(20:08) Insights on the blind spots of retirement planning software and AI’s role in financial planning(23:00) The emerging role of AI as a thinking partner in retirement planning(25:43) Managing required minimum distributions and tax planning for late retirees (Michelle’s situation)(28:08) Using professional help vs. DIY approaches for RMDs and taxes(31:24) Dan’s pursuit of a meaningful second career in financial literacy and how to prepareON THE BOOKSHELF(35:42) Recommended bookshelf: The Art of Spending Money, Devil in the White City, Inside the Greatest Crash, and Once an EagleSMART SPRINT(41:37) Smart Sprint: Create an experiential gift to cherish memories with loved onesREFERENCESThe Art of Spending Money by Morgan HouselDevil in the White City by Erik LarsonInside the Greatest Crash by Andrew Ross SorkinOnce an Eagle by Anton MyrerAging and Healthcare Planning ResourcesConnect with Roger Whitney:Submit a Question for RogerSign up for The NoodleNote: The opinions expressed are for informational purposes only and should not replace personalized advice from licensed professionals.
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Why Even the Best Retirement Calculator is Wrong
Mar 2500:59:32Tap to summarizeRoger 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 results, avoid common traps, and use software as a guide rather than a decision-maker so you can build a retirement plan that supports a great life.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 confidence to lean in and rock it.(00:30) Roger introduces the episode topic—why your retirement calculator’s success rate can be misleading.PRACTICAL PLANNING SEGMENT(02:50) Roger explains his perspective as a long-time practitioner and outlines his experience using Monte Carlo-based retirement tools.(05:05) Complicated vs. complex problems: why retirement can’t be “solved” like a math equation and must instead be managed over time.(09:30) Concerns about overreliance on software—from advisors scaling businesses to individuals misinterpreting results.(11:30) What retirement software actually measures.(13:25) What software does NOT measure.(14:18) Best uses of planning software.(17:40) What software should NOT be used for.(19:40) Key dangers of using retirement software.(23:00) Feasibility vs. resilience: why a plan that “works” on paper may still be fragile in real life.(24:20) The real risk:Overspending early and jeopardizing later yearsUnderspending and missing out on life(26:20) The massive number of assumptions behind every plan—and how small changes can dramatically alter outcomes over time.(38:20) How to interpret results properly.(40:55) Looking beyond the number: evaluating the distribution of outcomes and plan sensitivity.(44:43) Understanding failures:Timing (early vs. late failures)Severity (minor shortfall vs. major gap)(48:27) Best practices:Hold success rates lightlyKeep plans simpleRegularly review assumptionsAvoid over-planning and constant tweakingDefine what success actually means for your lifeSMART SPRINT(56:04) Schedule time to review the assumptions in your retirement planning software—focus on understanding the inputs rather than optimizing the output.CLOSING THOUGHTS(56:50) Roger shares an update on the merger of his firm with Tanya Nichols’ firm and the creation of a new company, Retire Agile.REFERENCESlivewithroger.com — Register for Noodle Live on March 28!Submit a Question for RogerSign up for The Noodle
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Retirement Talk with Dr. Wade Pfau
Mar 1801:01:09Tap to summarize💬 Show NotesWade 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 than a traditional risk tolerance questionnaire, how to think about real estate and reverse mortgages as retirement tools, and what the research actually says about annuities — including when to buy, whether to add inflation protection, and how fixed index annuities with living benefits really work. This podcast is a replay of a recent Rock Retirement Club meetup where members were able to join live and ask questions.Outline Of This Episode Of The Retirement Answer Man(00:00) Roger previews the episode and invites listeners to register for Noodle Live — a Saturday morning Zoom on March 28 at livewithroger.comCONVERSATION WITH DR. WADE PFAU(02:00) Roger introduces Wade Pfau, author of The Retirement Planning Guidebook (04:15) RISA vs. risk tolerance questionnaires(10:45) How to use The Retirement Planning Guidebook(12:00) AI in retirement research(14:30) RRC Member Question: How does real estate fit into retirement planning?(17:00) Reverse mortgages as a retirement tool — usage trends, how the HECM line of credit works, upfront cost hurdles, and why adoption remains low(21:30) RRC Member Question: What is an effective marginal tax rate (EMR) and how does it affect Roth conversion strategy? (25:00) Navigating ACA subsidy cliffs before Medicare(28:00) RRC Member Question: Fixed vs. inflation-adjusted annuities(33:00) Annuity timing(37:00) RRC Member Question: Should we explore intentionally breaking the ACA cliff every few years?(48:00) Fixed index annuities with living benefits vs. income annuities(53:00) RRC Member Question: Is there an optimal age window for buying an annuity if it's a "nice to have" rather than a must?(57:00) Interpreting retirement planning softwareSMART SPRINT(59:00) Pick up the latest edition of The Retirement Planning Guidebook. Use it as an approachable reference guide, or read it straight through if you're really into retirement planning.REFERENCESlivewithroger.com — Register for Noodle Live on March 28!The Retirement Planning Guidebook, 3rd Edition — Wade Pfau / retirementresearcher.comTake the RISA® assessment.Submit a Question for Roger.Sign up for The Noodle.
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