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
13 snips
Jan 14, 2026 • 54min
Retire on Fire- Rocking an Early Retirement: Henry and Lucy's FIRE Goals
In this engaging discussion, Henry and Lucy dive into their core values—like family and authenticity—that shape their vision for early retirement. They explore how to contribute meaningfully beyond traditional work while planning for financial goals. The couple discusses their base budget and aspirations such as travel and philanthropy. Listeners are encouraged to dream big and reflect on their own retirement goals amidst the wisdom shared by seasoned retirees. It's a journey filled with insights on purpose, flexibility, and making the most of retirement.
15 snips
Jan 7, 2026 • 50min
Retire on FIRE- Rocking an Early Retirement: Meet Henry and Lucy
In this episode, listeners meet Henry and Lucy, a couple in their 40s on a quest for Financial Independence and Early Retirement (FIRE). The discussion dives into the 4% rule and the 25x rule, exploring their benefits and limitations. Henry and Lucy share their journey toward FIRE, highlighting their intentional saving, frugality, and the non-financial motivations behind their early retirement goals. They also candidly discuss potential obstacles they'll face in a long retirement and the importance of updating financial plans.
9 snips
Dec 31, 2025 • 38min
Year-End Planning: Estimated Tax Payments
As the year wraps up, reflections on the power of words take center stage. The importance of estimated tax payments is highlighted to prevent nasty surprises in retirement. Listeners share corporate jargon they'd love to retire. Mick and Patty discuss enriching experiences in fitness and travel, emphasizing life's meaning in retirement. Roger introduces a unique practice of choosing a guiding word for 2026, sharing inspiring words from listeners, and reveals his own choice that embraces danger and change.
Dec 24, 2025 • 46min
Year-End Planning: The Basics of Charitable Giving
This engaging discussion delves into the essentials of charitable giving, emphasizing the importance of timing and documentation for year-end donations. Listeners learn about maximizing tax benefits through strategic contributions. A touching story of a listener's adventurous retirement highlights the value of purposeful living. Additional insights include the risks of high-yield bonds and the significance of clear communication after leaving corporate culture. The episode wraps up with reflections on generosity and crafting a meaningful retirement.
15 snips
Dec 17, 2025 • 40min
Year End Planning: RMD Rules for IRAs & Inherited IRAs
Dive into the complexities of inherited IRAs and how the SECURE Act reshaped the rules. Learn the distinctions between eligible and non-eligible beneficiaries and their tax implications. Discover the options available to surviving spouses and special considerations for minor children and disabled heirs. Get practical advice on using HSAs for health insurance and tips for creating more meaningful holiday conversations, including techniques to engage older relatives and enrich family stories.
Dec 10, 2025 • 41min
Year-End Planning: Annual Gifting Rules
Explore the nuances of annual gifting limits and year-end planning with practical strategies to enhance your giving experience. Discover why gifting during your lifetime can create lasting memories and reduce estate sizes. Learn to tie gifts to specific purposes for greater impact, and find out how gifting appreciated assets can lighten your tax burden. Engage with listener questions that shed light on early retirement planning and the importance of consulting a retirement planner to ensure financial security.
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!
