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by Roger Whitney, CFP, CIMA, RMA, CPWA
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.
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- 2 days ago58 min
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. Jordan Grumet, Roger discusses why retirement ultimately requires a leap of faith, how fear of running out of money can overshadow the risk of missing life, and practical ways to build confidence in spending and living intentionally. The episode also features listener reflections on decluttering, strategies for letting go of physical and financial clutter, and a Rockin’ Retirement in the Wild story from Scott, who recently retired and embraced a long-awaited trip to Maui.OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN Roger reflects on the “sweet and sour” nature of retirement and introduces the concept of taking a leap of faith. Roger welcomes listeners, previews his conversation with Dr. Jordan Grumet, and invites listeners to the upcoming Noodle Live event.ROCKIN’ RETIREMENT IN THE WILD Scott shares a retirement story from Maui, including a chance encounter with Roger’s realtor and reflections on taking the leap into retirement at age 57.PRACTICAL PLANNING SEGMENT WITH DR. JORDON GRUMET Roger and Dr. Jordan Grumet discuss why confidence can be one of the biggest challenges in retirement, even for those who have prepared well financially. The conversation explores the tension between protecting financial security and fully embracing life’s opportunities. ) A discussion on longevity assumptions, retirement planning conservatism, and why many retirees may overestimate the likelihood of running out of money. Practical strategies for building spending confidence, including the “fun bucket” approach. Additional tactics for creating confidence, including prefunding near-term spending and focusing on purpose rather than optimization. How values-driven planning can help retirees intentionally use money to support the life they want to create. Key takeaways on abundance, mindset, and taking meaningful action despite uncertainty.SMART SPRINT Identify one decision you've been researching, planning, or delaying. Ask yourself whether additional information will truly change the outcome, or if it's time to take a small leap of faith and move forward.DECLUTTERING DEBRIEF Roger reflects on listener feedback from the decluttering series and shares a few practical insights and resources from the community. REFERENCESlivewithroger.com — Register for Noodle Live on June 18!Submit a Question for RogerSign up for The NoodleDr. Jordan Grumet / Earn & Invest PodcastNote: The opinions expressed are for informational purposes only and should not replace personalized advice from licensed professionals.
- 1 weeks ago1h 1m
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 strategies from the Konmari method, focusing on identifying what truly sparks joy and letting go of the rest. This conversation is perfect for anyone looking to simplify their life and embrace a clutter-free future. OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN Roger previews the episode, announces the June 18 Noodle Live event, and introduces the final installment of the decluttering series.PRACTICAL PLANNING SEGMENT WITH LINDSEY HARDEGREE Roger frames retirement as a major life transition and explains how clutter extends beyond possessions into finances, commitments, and relationships. Lindsey introduces the KonMari framework and explains why the first step is creating a clear vision for your ideal life before getting rid of anything. Lindsey shares common scenarios that prompt people to seek out an organizer. Roger and Lindsey discuss practical ways to define what you want your environment and future life to feel like. Lindsey explains emotional attachment, sunk costs, and why gratitude can help people let go of possessions tied to previous seasons of life. Why decluttering by category—not room—creates better long-term results and why sentimental items should come last. Club members discuss challenges involving spouses, differing organizing styles, and when outside help may be more effective than family support. Lindsey addresses difficult situations involving aging parents, inherited belongings, and navigating sentimental attachment during life transitions. The discussion shifts toward handling deeply personal and sentimental items, including family keepsakes, clothing, photos, and children's memorabilia. Lindsey explains why organization systems should fit the person using them and how overly rigid systems can create frustration instead of simplicity. Resources and advice for finding professional organizers and deciding when support may be helpful.SMART SPRINT Pick one very small category of personal items—pens, office supplies, coffee mugs, hair clips, or something similar—and spend time decluttering only that category. Focus on building momentum and decision-making reps rather than trying to organize everything at once.REFERENCESlivewithroger.com — Register for Noodle Live on June 18!Submit a Question for RogerSign up for The NoodleMarie Kondo's Konmari MethodKonmari Certified OrganizersNational Association of Productivity & Organizing Professionals (NAPO)Book: The Life-Changing Magic of Tidying Up by Marie KondoNote: The opinions expressed are for informational purposes only and should not replace personalized advice from licensed professionals.
- 2 weeks ago44 min
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 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 Roger previews the episode, shares details about the upcoming Noodle Live event, and outlines the next phase of the decluttering series.PRACTICAL PLANNING SEGMENT Roger introduces one of the biggest challenges of decluttering: making the process feel too overwhelming and believing it has to be done perfectly. Roger explains why clutter often persists because it lacks urgency and people wait for a triggering event before taking action. He explores the emotional and practical obstacles tied to physical possessions, including memories, unfinished projects, family heirlooms, and sunk costs. Roger breaks down financial clutter and why accounts, relationships, taxes, and uncertainty can make simplification feel risky. He discusses relationship clutter, including obligations, organizations, unhealthy dynamics, and the fear of disappointing others. How do we overcome these challenges?LISTENER QUESTIONS Roger answers a question about whether global sentiment toward U.S. leadership should impact international versus domestic investment allocation decisions. A listener facing gray divorce asks for guidance, leading Roger to discuss grief, rebuilding identity, and creating a new vision for retirement. Roger shares his experience using MediShare and discusses important healthcare considerations before choosing alternatives to ACA coverage. Roger responds to listener feedback on longevity planning and balancing the risk of overspending versus running out of money.ROCKIN’ RETIREMENT IN THE WILD 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 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 16!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.
- 3 weeks ago39 min
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 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 Roger explains how decluttering helps reclaim your attention in a world competing for your focus. Roger previews week two of the decluttering series and introduces the themes of opportunity, risk tolerance, and listener questions.ROCKIN’ RETIREMENT IN THE WILD 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 Roger responds to a listener's question about how risk tolerance should fit into a three-bucket retirement strategy. He outlines why retirement planning should focus on building allocations from the ground up based on purpose and time horizon.PRACTICAL PLANNING SEGMENT Roger explores the opportunities created by decluttering your things, including reducing overwhelm, maintenance, and future burdens on loved ones. He discusses how simplifying finances can increase clarity, reduce anxiety, and create greater confidence in retirement. Roger explains how decluttering relationships and obligations can create space for more intentional connections. He highlights the importance of reducing digital and news clutter to protect your attention and mental bandwidth.LISTENER QUESTIONS Roger explains how donor-advised funds can help simplify a cluttered brokerage account while improving tax efficiency for charitable giving. He answers a widower’s question about Social Security survivor benefits, timing strategies, and earnings test considerations.SMART SPRINT 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 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.
- May 6, 202650 min
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 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 Roger introduces retirement as a “refresh” moment and explains why decluttering is essential to stepping into a new identity. Roger outlines the month-long decluttering series and introduces the three key domains: things, money, and relationships.ROCKIN’ RETIREMENT IN THE WILD 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 Roger defines the core problem of clutter, explaining how accumulated decisions create overwhelm and limit future possibilities. Roger explores physical clutter and how decades of possessions tied to past life stages can prevent you from envisioning a new lifestyle. He breaks down financial clutter, including scattered accounts and legacy investments, and why simplification becomes critical in retirement. Roger discusses relationship and obligation clutter, emphasizing the need to be intentional about who and what you invest your time in.LISTENER QUESTIONS A widow shares her experience navigating longevity risk and loss, prompting a discussion on planning flexibility, spending, and building a support network. 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. He evaluates whether an annuity recommendation actually solves a meaningful problem or simply adds complexity. Roger discusses the trade-offs between saving more versus using existing cash, highlighting flexibility and optionality in retirement planning.SMART SPRINT 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 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.
- Apr 29, 202657 min
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 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 This show is dedicated to helping you not just survive retirement, but have the confidence to lean in and rock it. Roger introduces the idea that we plan heavily for running out of money but rarely consider the probability of running out of life. Roger recognizes everyone who reached out about Sherlock’s passing and plays an audio message from a listener.ROCKING RETIREMENT IN THE WILD 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 Roger and Dr. Bobby explore why longevity assumptions are often flawed and how they directly impact how much money you think you need. The conversation shifts to the limits of predicting lifespan and the emotional and behavioral implications of trying to do so. 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 Roger introduces a practical approach to making more thoughtful longevity assumptions without overcomplicating the process.SMART SPRINT Use a simple longevity calculator to form a baseline assumption and decide how conservative you want to be in your planning.ON THE BOOKSHELF 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.
- Apr 22, 202648 min
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. 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 Building wealth for retirement and investment strategies.RETIREMENT TOOLKIT Basics of asset allocation and diversification. Explanation of unsystematic and systematic risks. Risk management and modern portfolio theory. Key components and decisions in portfolio construction. Key takeaways and practical advice. Importance of contingency, liquidity, and growth funds.LISTENER QUESTIONS T-Bone asks a question about asset allocation funds An audio question about portfolio diversification Michael asks about the ‘buy, borrow, die’ strategy Listener shares a suggestion for what to do with a t-shirt collectionROCKING RETIREMENT IN THE WILD Dennis shares that two years into retirement, he’s happy without a defined “purpose,” pushing back on the idea that retirement needs one. Tim and Tammy embrace a flexible “pre-tirement” lifestyle, teaching remotely while traveling, volunteering, and exploring all 63 U.S. national parks.SMART SPRINT Review your asset allocation and clearly define your contingency, liquidity, and growth buckets.CONCLUSION 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.
- Apr 15, 202647 min
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 your values.OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN PODCAST Introduction and overview of upcoming topicsRETIREMENT TOOLKIT Why inflation poses a significant risk to retirees What is inflation and how is it measured Causes of inflation: demand, supply constraints, and rising costs Historical inflation rates and what they mean for your planning How to choose a realistic inflation assumption in your plan Strategies to hedge against inflationROCKIN RETIREMENT IN THE WILD Jim’s story: diversity in retirement activities and the importance of adaptabilityPRACTICAL PLANNING SEGMENT Mike’s question reframed: focus on designing your retirement life first, not account tactics Roger reviews Mike’s facts The importance of building a feasible plan of record, estimating expenses, and creating a realistic monthly budget for retirement Clarifying values and how they shape your retirement goals Income side of the plan: social security, pensions, and tax considerations Once the plan is feasible, start testing versions of the plan and planning paycheck 401(k) and 457 decisions can wait—focus on positioning assets for income first Consider building after-tax savings now to increase future optionalityLISTENER QUESTIONS Listener shares story about roadside cafe Michael asks a question about ROTH conversions in a down market Steve asks how to better time Roth conversions to avoid triggering IRMAA Medicare surcharges?SMART SPRINT Smart Sprint: Before acting, ask yourself “what problem am I actually solving?”ON THE BOOKSHELF 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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About Retirement Answer Man
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.
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