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
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.
7 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!
26 snips
Sep 24, 2025 • 35min
The Difference Between an IRS Late Payment Penalty and Interest
Join tax expert Erin Coe, an enrolled agent, as she breaks down the maze of IRS penalties and interest that can catch retirees off-guard. Learn the crucial differences between tax penalties and interest accrual, and get tips on calculating estimated payments. Erin shares practical strategies like the use of Form 1040-ES and how withholding can save you from headaches down the line. Plus, hear an inspiring retirement success story from Lottie that emphasizes simplicity in planning for a stress-free retirement!
15 snips
Sep 17, 2025 • 38min
How to Read Your Social Security Statement
Discover how to read your Social Security statement with clarity and confidence. The discussion breaks down each section, emphasizing its importance for retirement planning. Listeners' questions spark insights into strategies for delaying retirement and navigating financial transitions, like divorce. Learn about the nuances of Roth conversions and the critical five-year rule. Gain essential knowledge for optimizing benefits and making informed financial decisions as you approach this exciting new chapter in life.
44 snips
Sep 10, 2025 • 49min
Don't Get Cute with Your Retirement Investments
Peter Lazaroff, Chief Investment Officer at Plancorp and author of 'Making Money Simple', shares his expertise on simplifying retirement investments. He discusses the common pitfalls of overcomplicating financial strategies and the cognitive biases that can lead to poor decisions. With insights on private equity, he highlights when these complex investments can be beneficial or detrimental. Lazaroff emphasizes the importance of keeping retirement planning straightforward, advocating for clarity and confidence in achieving financial goals.
31 snips
Sep 3, 2025 • 41min
Navigating Medicare in 2025
Join Medicare expert Danielle Roberts from Boomer Benefits as she unveils the essentials of navigating Medicare in 2025. Danielle shares crucial updates on Medicare Advantage and Part D changes that could alter your options. She highlights the importance of reviewing these plans annually to ensure you make informed decisions. With personalized assessments in mind, listeners learn to weigh the differences between Medicare Advantage and original Medicare. Plus, hear inspiring stories of retirees embracing life beyond healthcare choices!
20 snips
Aug 27, 2025 • 40min
Should I Do a "Free" Retirement Analysis?
Delve into the complexities of accepting free retirement analyses and uncover the hidden costs behind seemingly free offers. Hear a heartfelt story from a listener embracing the excitement of retirement. Learn essential strategies for rolling over 401k accounts and optimizing Social Security benefits. Discover the implications of free services and how they can impact your retirement planning. Tune in for practical tips and insights that empower you to navigate your retirement journey with confidence!
10 snips
Aug 20, 2025 • 46min
Direct Indexing vs. Mutual Fund or ETFs
Discover the nuances of direct indexing versus traditional investment options like mutual funds and ETFs. Learn how direct indexing can offer tax benefits and customization but may come with added complexity. Hear real-life experiences of retirees embracing e-bikes for exploration and connection. Navigate the emotional and financial waters of retirement with clarity, as different phases of planning—calm, choppy, and rough—are explored. Plus, gain insights into managing inherited money and the implications for your overall financial strategy.
13 snips
Aug 13, 2025 • 52min
Elder Care Options for Singles
Kathy McNair, an elder law attorney with over 20 years of experience, discusses vital elder care options for singles, focusing on legal preparedness. She clarifies the differences between guardianships and conservatorships, emphasizing the importance of documents like healthcare proxies. The conversation also touches on the unique challenges faced by solo retirees and the necessity of support systems. Roger adds insights on the significance of gratitude and contentment for a meaningful retirement, creating a well-rounded dialogue on planning for the future.
