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
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!
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.
