Retirement Answer Man

Roger Whitney, CFP®, CIMA®, RMA, CPWA®
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13 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!
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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.
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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.
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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!
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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!
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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.
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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.
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Aug 6, 2025 • 36min

How to Choose a Retirement Coach

💬 Show NotesIn this episode, Roger Whitney returns after a month off, ready to help you rock your retirement! He answers listener questions on a range of topics, including the benefits of choosing between Fidelity and Vanguard, the Rule of 55 for 401(k) withdrawals, and inherited IRA distributions. Roger also chats with  discusses the importance of finding the right retirement coach. Join us for practical advice and insights to help you navigate your retirement journey!OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN(00:00) Roger Whitney answers your retirement questions on today's showROCKIN’ RETIREMENT IN THE WILD(01:08) Brian says he and his wife are playing pickleball during retirement.CHAT WITH KEVIN LYLES(03:30) Roger talks to Kevin Lyles about a financial advisor versus a retirement coach(06:29) How does someone determine if they need an advisor or a coach?(10:15) Define what you are looking for before finding a coach.(12:44) A good coach will listen and have good intuition about what is really going on.LISTENER QUESTIONS (14:47) Barb says she was thinking of moving her Fidelity assets to Vanguard.(21:44) Mark has a question about the Rule of 55.(25:53) Craig asks a question about an inherited IRA(27:54) Scott says he has discovered something about TSP withdrawals.(30:53) An audio question about my Switzerland interview with Scott from a few weeks backSMART SPRINT(32:05) In the next seven days, define something you would like to do and find one person who has done this thing.BONUS(35:00) Roger reflects on how he is going to spend the next 5 weeks.REFERENCESThe Retirement Collective- BookThe Retirement Coaches AssociationSubmit a Question for RogerSign up for The NoodleThe Retirement Answer ManFOLLOW US ON SOCIALS!Follow Us on Facebook!Follow Us on Instagram
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4 snips
Jul 30, 2025 • 36min

Replay: How to Manage Your Scarcity Brain

In this episode, Roger Whitney welcomes Michael Easter, New York Times bestselling author of 'The Comfort Crisis' and 'Scarcity Brain.' They delve into the concept of overcoming frugality and the evolutionary mismatches that affect our resource management in retirement. Discover how short-term discomfort can lead to long-term growth, the importance of taking the stairs in life, and the psychological implications of our modern abundance. Tune in for insights that can help you not just survive retirement, but thrive in it!*Episode originally aired March 27, 2024OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN[01:04] Today we have Michael Easter, author of Scarcity Brain, on the show.PRACTICAL PLANNING SEGMENT WITH MICHAEL EASTER[02:20] Roger introduces Michael Easter to the show[03:14] The Comfort Crisis falls into the Energy Pillar- building energy so you can show up for your life.[04:30] Roger asks Michael what his objective was in exploring the Comfort Crisis[09:40] Why is it a bad thing to be comfortable?[12:40] How do we start being more uncomfortable?[16:11] The Scarcity Brain falls into the Vision Pillar.[18:00] Why do we have a constant feeling that we don’t have enough?[25:25] Quantifying goals is not always the best thing to do.[29:01] Michael defines what the scarcity loop is.TODAY’S SMART SPRINT SEGMENT[33:21] In the next seven days, take the stairs! Do something that most people don't do.RESOURCESBOOK - The Comfort Crisis by Michael EasterBOOK - Scarcity Brain by Michael EasterStutzRock Retirement ClubFOLLOW US ON SOCIALSFollow Us on Facebook!Follow Us on Instagram
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22 snips
Jul 23, 2025 • 29min

Replay: Overcoming Frugality in Retirement with Dr. Dan Crosby

Dr. Daniel Crosby, Chief Behavioral Officer at Orion Advisory Services, delves into the psychological hurdles retirees face in shifting from saving to spending. He highlights the struggle many experience with frugality and provides practical strategies to embrace spending confidently. The conversation emphasizes the importance of experiences over accumulated wealth, urging listeners to prioritize meaningful moments with loved ones. Discover how to overcome regret aversion and transform your retirement into a fulfilling journey, rather than holding back out of fear.

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