Retirement Answer Man

Roger welcomes Danielle Roberts, co-founder of Boomer Benefits, to discuss Medicare in 2026, including rising Part D premiums, Medicare Advantage versus Medigap, and what to review during open enrollment. Then, Roger shares a Rock Retirement Club case study about building an income reserve before retirement and finding peace of mind by focusing on what matters most. OUTLINE OF THIS EPISODE OF THE...

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 Social Security survivor benefits, weighing a teacher pension lump sum against a higher annual payment, what...

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 purpose, manage risk, evaluate stocks and bonds, and create a simple investment process you can actually sti...

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 for a perfect answer. OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN PODCAST  (00:00) Roger Whitne...

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 simple action step for deciding when to revisit the issue. OUTLINE OF THIS EPISODE OF THE RETIREMENT A...

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 the best claiming strategy depends on each person’s priorities, resources, and desired outcome. OUTLINE...

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 agency as you build your Social Security claiming strategy. Roger also answers listener questions about surv...

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 current financial outlook. He also discusses potential paths to solvency, how he accounts for Social Sec...

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 EPISODE OF THE RETIREMENT ANSWER MAN [00:00] Roger introduces this summer replay with Dr. Daniel Crosb...

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 this Summer Replay conversation with Gretchen Rubin about creating a retirement plan that fits your pe...

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 supporting your retirement should remain separate from any “play money” used to explore alternative invest...

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. Together, they explore the unique planning considerations for single retirees, including building a trusted...

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 for?" can reduce financial stress, improve decision-making, and help align your spending with the life you...

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 explains why financial optimization should be measured by the life it enables rather than the dollars it saves...

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 current lifestyle and your future needs. Along the way, he answers listener questions about speculative inv...

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 unpacks stepped-up cost basis, covering how it works, when it matters, and how it can become a valuable est...

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 accounts they affect, how they're calculated, and strategies for managing them through retirement. List...

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. Listener questions cover gifting strategies with adult children, Social Security claiming options for spo...

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 conversion assumptions, choosing between a pension and lump sum, whether the Shiller PE ratio can predict ma...

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 why investors need clarity around what they are paying so they can determine whether they are receiving e...

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 o...

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. Th...

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 unc...

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 questionnaire...

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 d...