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Retirement Answer Man

Retirement Answer Man

Roger Whitney, CFP®, CIMA®, RMA, CPWA® 653 Episodes Aug 19, 2026

A top retirement podcast hosted by Roger Whitney, a certified financial planner. It covers both financial and personal aspects of retirement, including creating a paycheck, Medicare, Social Security, tax management, and non-financial topics like travel. The podcast aims to help listeners retire with confidence and find balance between living well today and feeling secure about the future.

Episodes

Summer Reruns: Gabbing with Gretchen Rubin- Your Personality and How it Plays into Your Retirement Planning
Summer Reruns: Gabbing with Gretchen Rubin- Your Personality and How it Plays into Your Retirement Planning Aug 19, 2026 1284 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
Summer Reruns: Keep Investments Simple with Peter Lazaroff
Summer Reruns: Keep Investments Simple with Peter Lazaroff Aug 12, 2026 2503 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 alternati
Summer Reruns: Retiring Single with Tanya Nichols
Summer Reruns: Retiring Single with Tanya Nichols Aug 5, 2026 1493 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
Retirement Toolkit: Never Worry About Money Again with Jesse Mecham
Retirement Toolkit: Never Worry About Money Again with Jesse Mecham Jul 29, 2026 3931 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
Retirement Toolkit: How do you Balance Optimization with Simplification
Retirement Toolkit: How do you Balance Optimization with Simplification Jul 22, 2026 3189 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
Retirement Toolkit: How to Rebalance a Retirement Portfolio
Retirement Toolkit: How to Rebalance a Retirement Portfolio Jul 15, 2026 3311 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 specul
Retirement Toolkit: How Does Step Up in Cost Basis Work
Retirement Toolkit: How Does Step Up in Cost Basis Work Jul 8, 2026 2958 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 val
Retirement Toolkit: How Required Minimum Distributions (RMDs) Work
Retirement Toolkit: How Required Minimum Distributions (RMDs) Work Jul 1, 2026 2751 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 retirem
IRMAA: The Medicare Premium Surprise and How to Avoid It
IRMAA: The Medicare Premium Surprise and How to Avoid It Jun 24, 2026 2977 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 option
Mutual Funds vs. ETFs- Which is Better for Retirement?
Mutual Funds vs. ETFs- Which is Better for Retirement? Jun 17, 2026 3876 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 p
Know What You Pay: A Guide to Investment & Advice Costs
Know What You Pay: A Guide to Investment & Advice Costs Jun 10, 2026 2516 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 re
Take the Retirement Leap of Faith with Jordan Grumet
Take the Retirement Leap of Faith with Jordan Grumet Jun 3, 2026 3536 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

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