Retirement Answer Man
Roger Whitney, CFP®, CIMA®, RMA, CPWA®
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
Mentioned books
11 snips
Dec 3, 2025 • 37min
Year-End Planning: Tax-Loss Harvesting
Dive into year-end retirement planning as tax loss harvesting steals the spotlight! Gain insights on minimizing capital gains tax by offsetting gains with realized losses. Understand the difference between short-term and long-term capital gains, plus learn how to navigate the IRS wash sale rule. Roger shares a step-by-step process to optimize your tax strategy before the year's end. Don't miss the smart sprint action item to boost your financial moves and the inspiring retirement pivot from a listener!
6 snips
Nov 26, 2025 • 38min
Should I Use My Traditional IRA to Fund My Life or Do Roth Conversions?
In a thought-provoking discussion, the host dives into the complexities of using traditional IRAs versus pursuing Roth conversions for retirement funding. He emphasizes the importance of context in making these decisions. Listeners are encouraged to observe their financial needs before making withdrawals. The benefits of both distributions and conversions are explored, weighing tax implications and future planning strategies. On a lighter note, a challenge is issued to express specific gratitude, making thankfulness a part of everyday life.
Nov 19, 2025 • 36min
My Advisor Recommended an Annuity. Should I Buy It?
Explore the ins and outs of required minimum distributions (RMDs) and why they matter for retirement savings. Learn about the different age thresholds and calculation methods based on IRS tables. Discover strategies to minimize future RMDs and the implications for long-term planning. Plus, delve into the pros and cons of annuities—what to consider before committing to one. Roger also answers listener questions on gifting safely without compromising retirement security, ensuring a well-rounded approach to financial planning.
Nov 12, 2025 • 39min
How Do I Build My Initial Cash Cushion for Retirement?
Delve into the fascinating concepts of loss aversion and its impact on financial choices. Explore the newly launched Retirement Toolbox, packed with practical tools like Qualified Charitable Distributions that offer tax benefits. Learn strategies for building retirement reserves while avoiding tax pitfalls. Discover why retirement plans should be flexible guides instead of strict rules, and gain insights on stress-testing for potential risks. Roger also shares his book collection journey, inviting suggestions from listeners along the way!
17 snips
Nov 5, 2025 • 46min
The 10 R's for a Joyful Retirement with Cesar Aguirre
Cesar Aguirre, an author and former C-level executive, shares his insights on transitioning to retirement with purpose. He discusses the importance of aligning retirement goals with personal values rather than merely chasing achievements. Cesar also highlights how his journaling process led to his book, which serves as a guide for others. Cultural perspectives on retirement and actionable tips for new retirees enrich the conversation, emphasizing the need for structure in planning this new chapter of life.
31 snips
Oct 29, 2025 • 52min
Retirement Goal Case Study
In this insightful discussion, concepts like buoyancy and Maslow’s hierarchy of needs are linked to successful retirement planning. Roger introduces two intriguing avatars—the Grinder, focused on safety, and the Dreamer, chasing self-actualization—each with distinct desires and challenges. The conversation reveals practical strategies for addressing triggers that prompt re-evaluation of retirement plans. Listeners gain personalized insights into balancing these archetypes for a fulfilling retirement journey, making planning not just secure, but truly inspiring!
18 snips
Oct 22, 2025 • 56min
How to Navigate Goals as Life Unfolds
Dr. Bobby, a physician and podcast host, dives into the nuanced world of organic foods. He reveals the significant cost differences of organic groceries, often running 50% higher than conventional options. They discuss the opportunity cost of choosing organic over saving for retirement or investing in health. Surprisingly, Dr. Bobby emphasizes that simply increasing fruit and vegetable intake offers greater health benefits than going organic. The conversation also touches on the emotional allure of organic choices and suggests strategic purchasing for maximum benefit.
31 snips
Oct 15, 2025 • 46min
Building Agile Retirement Goals
Explore the art of creating agile retirement goals focused on personal self-discovery. Discover how to set meaningful low-stakes goals that allow for experimentation in your retirement journey. Learn about the importance of revisiting values and building a solid foundation for fulfillment. Roger discusses the differences between high-stakes and low-stakes goals, and how to leverage your year-by-year experiences to find what truly brings joy. Tune in for insights on navigating your retirement with confidence and flexibility!
21 snips
Oct 8, 2025 • 32min
Setting Retirement Goals: The Paradox of Knowing What You Want
Explore the challenges of articulating what you truly want in retirement. Understand why simply asking about retirement spending can be misleading. Discover the downside of following societal scripts and the pitfalls of overly detailed goals. Learn how to create conditions that foster a fulfilling retirement experience. Listen for practical advice on managing inherited IRAs and the optimal timing for joining retirement communities. Plus, get essential tips for family estate planning and an invitation to reflect on your retirement goals.
19 snips
Oct 1, 2025 • 59min
Simple Isn't Easy: Carl Richards on Life and Retirement
Carl Richards, a financial advisor-turned-artist and the mind behind insightful sketches in personal finance, discusses the power of 'elegant simplicity' in retirement planning. He shares his journey from sketches to best-selling books, emphasizing the importance of knowing your true desires, influenced by social cues. The conversation covers how to gather actionable information, balance heart and logic in decision-making, and the significance of experimentation to clarify retirement goals. Discover how to replace work identity with meaningful pursuits!
