Roger Whitney kicks off a month-long series on navigating health care before Medicare, introducing Cerberus—the three-headed dog of Greek mythology—as a framework for understanding the biggest challenges retirees face when leaving employer-sponsored coverage. He breaks down the three heads of Cerberus, answers listener questions about retirement planning, and shares recent book recommendations from himself and the team.

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN

• (00:00) This show is dedicated to helping you not just survive retirement, but have the confidence to lean in and rock it.
• (00:30) Roger introduces the Cerberus framework and outlines the four-week series on health care before Medicare.

HEALTH CARE BEFORE MEDICARE: THE THREE HEADS OF CERBERUS

• (02:20) Roger explains why retiring before Medicare requires a strategy and introduces the three “heads” of the health care Cerberus.
• (03:11) “Head” #1: The true cost of health care without an employer subsidy and why it creates sticker shock in retirement, especially when paid from pre-tax accounts.
• (10:50) “Head” #2: Coverage challenges, including narrower networks, fewer plan options, and the potential loss of trusted doctors and specialists.
• (15:13) “Head” #3: Increased complexity in choosing plans, managing care, and navigating ACA subsidies based on modified adjusted gross income.

LISTENER QUESTIONS & OBSERVATIONS

• (19:20) Roger responds to listener questions about saving discipline, the 4% rule, geographic cost differences, values-based planning, and how taxes are modeled in retirement case studies.

SMART SPRINT

• (33:00) Roger encourages listeners to review the health care assumptions in their retirement plan, especially for those retiring before Medicare age.

WHAT’S ON THE BOOKSHELF

• (34:14) Roger and the team share recent book recommendations, including history, personal finance, purpose, habits, and wealth.

REFERENCES

• Submit a Question for Roger
• Sign up for The Noodle
• The Retirement Answer Man
• Kaiser Family Foundation (KFF)
• Healthcare.gov
  
  

As the Retirement Plan Live series wraps up, Roger Whitney shares wisdom from retirees further along the path to help Henry and Lucy think beyond the numbers. Listeners in their 50s, 60s, and 70s reflect on purpose, work, health, money, and joy—offering perspective on what really matters when retiring early. Roger closes with his own observations from decades of coaching, a Smart Sprint focused on learning from others, and listener-submitted words for the year.

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN

• (00:00) This show is dedicated to helping you not just survive retirement, but to have the confidence to lean in and rock it.
• (01:33) Two announcements: next month starts a healthcare-before-Medicare series and the listener survey in The Noodle is coming soon.

WISDOM FROM RETIREES FURTHER ALONG

• (03:41) Roger reads listener reflections from retirees further along, sharing lessons on purpose, work, health, flexibility, and building a meaningful retirement.

ROGER’S OBSERVATIONS 

• (12:54) Roger shares his observations from decades of coaching on what leads to a fulfilling retirement, including permission, projects, community, service, and avoiding distraction or scarcity thinking.

SMART SPRINT

• (22:12) Identify one challenge you’re facing and talk with someone who has already walked that path—before turning to books or the internet.

LISTENER WORDS FOR THE YEAR

• (25:10) Roger shares listener words for the year and the personal meaning behind them.

RESOURCES

• Sign up for our next webinar!
• Submit a Question for Roger
• Sign up for The Noodle
• The Retirement Answer Man
  
  

As the Retirement Plan Live case study continues, Roger Whitney helps Henry and Lucy move from dreaming to feasibility, organizing the real financial resources available to support an early retirement in their 40s. This episode centers on trade-offs, confidence, and the reality of giving up earned income decades early. Roger and the couple walk through income assumptions, assets, and risk tolerance before closing with listener advice, a Smart Sprint, and words for the year.

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN

• (00:00) This show is dedicated to helping you not just survive retirement, but to have the confidence and comfort to lean in and rock retirement.
• (00:27) Roger introduces Week 3 of the Retirement Plan Live case study with Henry and Lucy.
• (02:15) What are Henry and Lucy giving up to retire early?

RETIREMENT PLAN LIVE

• (05:00) Roger asks Henry and Lucy if they pick a word of the year.
• (06:05) Henry and Lucy reflect on why retiring even one year earlier feels uncomfortable without proof.
• (10:50) Review of Social Security assumptions and why it’s excluded from their base plan.
• (14:13) Confirmation that the plan assumes no earned income after retirement.
• (20:40) Overview of after-tax assets, cash buckets, and sinking funds.
• (26:20) Review of retirement accounts, savings rates, and long-term strategy.
• (31:30) Home equity, college savings, and inheritance assumptions.
• (33:40) Clarifying the goal for the after-tax bridge bucket.

ADVICE FROM A RETIREE

• (38:39) Listener Bonnie shares an alternative approach using sabbaticals and flexible work.
• (41:10) Roger reflects on optionality, skill relevance, and maintaining professional networks.

SMART SPRINT

• (42:30) Roger encourages listeners to organize or update their net worth statement.

WORD FOR THE YEAR

• (43:40) Listener Alex shares his word for the year: Healing.
• (45:10) Listener Valerie shares her word for the year: Minimize.

REFERENCES

• Sign up for our next webinar!
• Submit a Question for Roger
• Sign up for The Noodle
• The Retirement Answer Man
  

As the Retirement Plan Live case study continues, Roger Whitney helps Henry and Lucy articulate what they want their FIRE retirement to actually look like—starting with values, dreaming without constraint, and then translating that vision into concrete goals. Along the way, Roger shares wisdom from older retirees about purpose, productivity, and flexibility, invites listeners to reflect on their own “magic,” and closes with a Smart Sprint and listener-submitted words for the year.

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN

• (00:00) This show is dedicated to helping you not just survive retirement, but to have the confidence and clarity to lean in and rock it.
• (00:23) Roger previews today’s focus: Henry and Lucy’s retirement goals, advice from seasoned retirees, a Smart Sprint, and listener words for the year.
• (01:00) Roger explains why retirement planning should begin with dreaming big—starting with “everything” before testing feasibility.

RETIREMENT PLAN LIVE

• (03:25) Henry and Lucy walk through their core values and how those values shape their vision for retirement.
• (05:55) Roger reviews and discusses Lucy’s top ten values.
• (09:29) Henry talks about his top values.
• (11:40) Roger reflects on whether retiring early means “burying” one’s gifts, and considers how purpose and contribution can take many forms beyond traditional work.
• (13:44) Roger talks through Henry and Lucy’s goals for retirement and their budget for a great base life.
• (19:47) Lucy breaks down her thought process on her great base life budget.
• (23:00) Henry weighs in with his thoughts on their great base life.
• (24:05) They review discretionary goals such as travel, a camper van, hobbies, and future family commitments.
• (27:55) Lucy and Henry talk about aspirational wishes.
• (35:00) Lucy talks about how they react during uncertain times.

WISDOM FROM RETIREES FURTHER ALONG

• (41:41) Listener Mike shares why he chose “FILE” (Financially Independent, Living Early) instead of full FIRE, emphasizing purpose and reduced stress.
• (45:10) Listener Renee offers perspective on flexibility, one spouse stepping away from work, and how lower stress improved family life.

SMART SPRINT

• (48:08) Roger encourages listeners to separately write down their own “magic” retirement goals—without self-editing—then share and discuss them with their partner.

WORD FOR THE YEAR

• (50:07) Roger shares listener words for the year.

CLOSING THOUGHTS

• (53:17) Roger previews next week’s episode, where Henry and Lucy’s assets and resources will be evaluated to see what is feasible.

REFERENCES

• Sign up for our next webinar!
• Submit a Question for Roger
• Sign up for The Noodle
• The Retirement Answer Man
  
  

As the new year begins, Roger Whitney launches a new Retirement Plan Live case study, introducing Henry and Lucy, a couple in their mid-40s pursuing Financial Independence and Retire Early (FIRE). Roger revisits the 4% rule as a planning heuristic, explains when it can be helpful, and sets the stage for a live community analysis later this month. The episode closes with a Smart Sprint focused on updating your net worth statement and a listener’s word for 2026.

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN

• (00:00) This show is dedicated to helping you not just survive retirement, but to have the confidence to lean in and rock it.
• (00:30) Roger introduces a new Retirement Plan Live case study series and previews the upcoming live community meetup on January 29.

RETIREMENT TOOLKIT

• (01:58) Roger revisits the 4% rule, explaining what it is, where it came from, and why it is often misunderstood.
• (04:55) Roger talks about the 25x rule commonly used in the FIRE community.
• (06:38) He discusses the drawbacks of using these heuristics and who they are best used for.
• (11:05) Roger shares how the 4% rule can help overfunded retirees move beyond scarcity and spend more intentionally.
• (13:55) A breakdown of FIRE- Financial Independence, Retire Early.

RETIREMENT PLAN LIVE

• (17:41) Roger introduces Henry and Lucy.
• (20:01) They share how they discovered FIRE and what it means to them.
• (23:10) Lucy reflects on spending habits, saving, and budgeting
• (25:30) Henry talks about the start of their relationship.
• (28:12) Henry and Lucy discuss how saving impacted their lifestyle.
• (31:20) They discuss what drives their desire to retire early.
• (32:55) Roger reflects on his first impression of the FIRE Movement.
• (34:15) What are the obstacles of retiring so early?
• (38:45) Roger talks about the difference between a complicated problem and a complex problem.
• (40:35) Roger asks if they think about landmines that could pop up with such a long retirement.
• (43:57) Roger invites listeners further along the retirement path to share perspective and advice for their 40-something selves.

SMART SPRINT

• (45:20) Roger encourages listeners to update their end-of-year net worth statement and identify trends for the year ahead.

WORD OF THE YEAR

• (47:31) Listener Lindsay shares her word for 2026: Listen, and Roger reflects on the value of deep listening.

REFERENCES

• Submit a Question for Roger
• Sign up for The Noodle
• The Retirement Answer Man
• Livewithroger.com
• The Millionaire Next Door: The Surprising Secrets of America's Wealthy- Thomas J Stanley, Ph.D.
  
  

As the year comes to a close, Roger Whitney reflects on the power of words, walks through an important year-end tax planning reminder for retirees, shares listener stories and perspectives, and invites listeners to choose a guiding word for 2026 as a way to approach retirement with greater intention and clarity.

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN

• (00:00) This show is dedicated to helping you not just survive retirement, but have the confidence and clarity to lean in and rock it.
• (00:45) Roger reflects on slowing down, reclaiming meaning in familiar words, and recommitting to clearing the battlefield as we head into a new year.

RETIREMENT TOOLKIT

• (03:22) Roger explains why estimated quarterly tax payments matter in retirement and how they can help prevent unwelcome tax surprises.
• (05:44) He outlines safe harbor rules and practical best practices for withholding taxes from Social Security, IRA distributions, and pensions.

RETIREMENT LIFE LAB

• (13:33) Roger shares listener responses about corporate words and phrases people are eager to retire when they leave the workforce.

ROCKING RETIREMENT IN THE WILD

• (19:33) Mick and Patty share reflections on fitness, travel, and meaning in retirement, including experiences shaped by history and family.

FOCUSING FORWARD: A WORD FOR 2026

• (21:10) Roger discusses the practice of choosing a single word to define the coming year and reads listener-submitted words for 2026.
• (28:40) Roger reveals his own word for 2026.

SMART SPRINT

• (34:07) Roger encourages listeners to reflect on the season they are entering and consider choosing a word to help guide decisions in 2026.

CLOSING THOUGHTS

• (34:55) Roger responds to listener feedback on charitable giving and enjoying retirement, emphasizing balance, generosity, and intentional living as the year ends.

REFERENCES

• Submit a Question for Roger
• Sign up for The Noodle
• The Retirement Answer Man
• Financial Calculators from Dinkytown.net
  
  

In this Christmas Eve episode, Roger Whitney explores the basics of charitable giving as part of an intentional retirement plan, with a timely focus on year-end decisions. He explains how charitable deductions work, common planning mistakes to avoid, and why generosity is most effective when paired with a resilient financial plan. Roger also shares a Rocking Retirement in the Wild story from a listener who is actively living a purpose-filled retirement, reflects on the corporate language we can leave behind when we retire, and answers listener questions on retirement readiness, gifting inheritance early, and the risks of relying on high-yield bonds for retirement income. He closes the episode with personal reflections on lessons learned, reminding listeners how to keep retirement simple, resilient, and meaningful while making a positive impact on others.

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN

• (00:00) This show is dedicated to helping you not just survive retirement, but confidently lean in and rock it.
• (00:20) Roger introduces a Christmas Eve episode focused on charitable giving, listener stories, answering questions, and reflecting on intentional retirement living.

RETIREMENT TOOLKIT

• (03:45) Roger walks through the basics of charitable giving, including qualified charities, documentation requirements, and how deductions work with standard versus itemized returns.
• (07:55) Year-end timing rules for checks, credit cards, stock transfers, and donor-advised funds.

ROCKIN’ RETIREMENT IN THE WILD

• (09:30) A listener shares how, at 67, he backpacked 121 miles through Maine’s 100-Mile Wilderness, reconnecting with longtime friends and staying physically engaged in retirement.
• (12:28) Roger reflects on why rocking retirement doesn’t have to be impressive—only meaningful to the person living it.

RETIREMENT LIFE LAB

• (13:03) Roger explores the idea of “retiring” corporate jargon in retirement and how simplifying language can help us reconnect and speak more human again.
• (18:21) Listeners are invited to share the words and phrases they are most looking forward to leaving behind.

LISTENER QUESTIONS

• (19:50) Don asks why most people enter retirement with relatively little savings and what that reality means for financial and social stability.
• (29:25) A listener asks how to give inheritance before death without triggering taxes.
• (33:46) James asks whether using high-yield corporate bonds as the foundation for retirement income is a safe strategy.

SMART SPRINT

• (42:08) In the next seven days, Roger challenges listeners to choose a single word for 2026 to serve as a guiding focus for the year ahead.

CLOSING THOUGHTS

• (43:59) Roger shares final reflections on the lessons of the episode, emphasizing elegant simplicity, financial resilience, and showing up to help others in meaningful ways.

REFERENCES

• Submit a Question for Roger
• Sign up for The Noodle
• The Retirement Answer Man
  
  

In this episode, Roger Whitney walks listeners through the complexities of inherited IRAs, highlighting the impact of the SECURE Act of 2019 and clarifying the distinctions between eligible and non-eligible designated beneficiaries. He explains how these classifications affect withdrawals and tax planning, making the rules easy to understand. Roger also answers listener questions on topics like retirement team selection and funding health insurance with HSA accounts. Beyond the numbers, he shares practical strategies for creating more meaningful holiday conversations, drawing on real-life examples to show how curiosity and intentionality can help you connect more deeply with the people you care about.

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN

• (00:00) This show is dedicated to helping you rock retirement.
• (00:30) In today’s episode, Roger Whitney covers the rules around inherited IRAs, explores ways to foster deeper and more meaningful conversations during the holidays and beyond, and answers listener questions.

RETIREMENT TOOLKIT

• (01:00) Today ​in ​the ​Retirement ​Toolkit ​we're ​going ​to ​talk ​about ​the ​rules ​around ​inherited ​IRAs.
• (02:40) Differences between eligible and non-eligible designated beneficiaries for inherited IRAs are explained.
• (14:32) Roger talks about ROTH IRAs and how they work.

RETIREMENT LIFE LAB

• (16:04) Roger explains how approaching conversations with curiosity and intentionality, especially with older family members or those with different interests, can create more meaningful and enriching interactions.

LISTENER QUESTIONS

• (25:37) Ira asks what to ask a financial advisor’s team to understand their retirement planning services and team longevity.
• (37:02) Mary Jane asks if she can use Health Savings Account funds tax-free to pay for private health insurance premiums before Medicare eligibility.

SMART SPRINT

• (38:42) In the next week, approach holiday or New Year’s gatherings with curiosity by asking questions and engaging with people you don’t see often to create more meaningful interactions.

REFERENCES

• 
  Submit a Question for Roger
• Sign up for The Noodle
• The Retirement Answer Man
  
  

In this episode, Roger Whitney, a retirement planner with 30 years of experience, breaks down annual gifting limits and year-end planning. He shares practical strategies for giving that make a real impact and create meaningful experiences for loved ones. Roger also answers listener questions, providing clear guidance to help you navigate your retirement with confidence.

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN

• (00:00) This podcast is dedicated to helping you rock retirement.
• (00:57) Today Roger talks about annual gifting limits.

RETIREMENT TOOLKIT

• (01:45) In today’s Retirement Toolkit, Roger explores year-end planning by breaking down the 2025 annual gift exclusion.
• (04:05) Roger discusses giving money during your lifetime and shares the reasons why it can be beneficial.
• (12:05) Roger shares his observations on giving money, noting that gifts can feel most meaningful when attached to a specific purpose rather than given with expectations.
• (14:21) Strategies for impactful gifting are explored, including transferring appreciated assets, paying medical expenses, and covering tuition directly, showing ways to help others while maximizing meaning and efficiency.

LISTENER QUESTIONS

• (19:00) Mary shares feedback on qualified charitable distributions (QCDs).
• (21:27) Lee describes his “shoulder bonus” strategy to spend excess retirement funds while staying within a safe withdrawal rate.
• (30:10) John asks when to switch from a general financial advisor to a retirement planner
• (34:19) Rick asks about gifting appreciated stocks to adult children.
• (35:17) Steve asks about building a resilient retirement plan at age 80.

SMART SPRINT

• (38:13) In the next seven days: Do you want to give? Can you? How much and to whom? Can it have a purpose? Even small gifts can make a big impact.

CLOSING THOUGHTS

• (40:00) Giving money can bring profound joy, often the greatest gift is the one you give yourself by helping others. 

REFERENCES

• Submit a Question for Roger
• Sign up for The Noodle
• The Retirement Answer Man
  
  

💬 Show Notes

In this episode, Roger Whitney kicks off a month-long series on year-end planning for retirement. He shares insights on tax loss harvesting, a technique that can help you minimize capital gains tax. Listen in as Roger explains the basics of capital gains, the importance of proactive planning, and the potential benefits of offsetting gains with losses. Plus, he introduces a smart sprint action item to help you optimize your tax strategy before the year's end!

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN

• (00:00) This podcast is dedicated to helping you rock retirement.
• (01:07) Roger shares that he recently finished George Orwell’s 1984, his first in a new hobby of collecting classic authors.

RETIREMENT TOOLKIT 

• (03:43) Roger breaks down the basics of tax loss harvesting, explaining capital gains, the difference between short-term and long-term gains, and how they impact year-end retirement planning.
• (09:17) Roger explains how to implement tax loss harvesting by estimating your realized capital gains, identifying losses in your taxable accounts, selling positions to offset gains, and being mindful of the IRS wash sale rule that prevents repurchasing the same security within 61 days.
• (16:50) Using losses in taxable accounts strategically can help reduce capital gains taxes.

ROCKIN’ RETIREMENT IN THE WILD

• (18:28) Share your story of rocking retirement at askroger.me to inspire others with your confidence and passion.
• (19:30) Mark plans to pivot into business consulting after retiring so he can keep learning, adding value, and connecting with people while enjoying more freedom and purpose.

LISTENER QUESTIONS

• (21:54) Richard is preparing for retirement at 67 and asks how he should handle his 401(k) and income to make his plan work best.
• (25:00) Kathy asked how a new bill will affect those 65+ with year-end tax planning, and Roger said he’ll provide a checklist to guide Noodle subscribers through the changes.
• (25:42) Karen pointed out that annuity payments aren’t inflation-adjusted and emphasized balancing them with other investments.
• (30:08) Dan asks: “Where should I keep the cash for living expenses and market downturns?”

SMART SPRINT

• (33:59) Smart Sprint: In the next seven days, review your after-tax investment accounts, estimate year-end capital gains or losses, and consider selling positions with unrealized losses to offset gains while avoiding the 31-day wash sale rule.

CLOSING THOUGHTS

• (35:18) Over Thanksgiving, Roger continued his childhood tradition of watching the Lions lose, ending up jumping in a pool after a bet with his nephew Graham, a devoted Packers fan.

REFERENCES

• 1984- George Orwell
• Submit a Question for Roger
• Sign up for The Noodle
• The Retirement Answer Man