Retirement Answer Man

Roger Whitney wraps up the four-part series on navigating health care before Medicare by introducing a practical decision-making framework using the OODA Loop—observe, orient, decide, act—to help you avoid unforced errors and make a confident judgment call. He walks through organizing your retirement cash flow, estimating MAGI and ACA subsidy eligibility, evaluating COBRA, ACA, and private coverage options, and weighing tax optimization against simplicity and continuity of care. He’s joined by Taylor Schulte of Define Financial to discuss how professionals navigate Roth conversions, Social Security timing, ACA cliffs, and the trade-offs between optimizing for subsidies versus long-term tax planning.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 final week of the health care before Medicare series and previews upcoming episodes with Harry Reese (co-author of How to Feel Loved) and retirement researcher Wade Pfau.PRACTICAL PLANNING SEGMENT(02:30) Roger reviews the three “heads” that must be managed before Medicare- cost, continuity of care, and complexity.(03:30) Roger talks about avoiding unforced errors that could cost you money, disrupt care, or create unnecessary stress.(05:18) Roger introduces the OODA Loop—observe, orient, decide, act—as a practical way to think step by step about health coverage choices. (05:52) Observe: Build a 5-year retirement income and spending plan, estimate taxes and MAGI, identify where you fall relative to the ACA subsidy cliff, and review withdrawal sources (taxable, pre-tax, Roth) along with future RMD implications.(14:21) Orient: Clarify what matters most to help you make a decision.(20:00) Decide & Act: Choose a direction, document your reasoning, update your plan of record, and implement the distribution strategy that supports your choice.CONVERSATION WITH TAYLOR SCHULTE(22:25) Roger introduces Taylor Schulte from Define Financial(23:15) Why health care before Medicare shouldn’t automatically delay retirement and how assumptions often go untested.(26:50) Evaluating alternatives beyond ACA, including COBRA as a short-term bridge and private plans.(31:50) The tension between Roth conversions and ACA subsidies, and how Social Security timing affects MAGI.(34:20) Avoiding the “optimization trap”: sometimes paying more for simplicity still results in a resilient retirement plan.(36:40) The key takeaway is that there’s no perfect answer—retirees should explore options, make informed decisions without fear, and use healthcare planning as a tool rather than a barrier or excuse to delay retirement.SMART SPRINT(43:35) Set a reminder to review your health care strategy using a structured approach—especially if retirement or Medicare enrollment is approaching. The goal is to be intentional, not reactive.REFERENCESSubmit a Question for RogerSign up for The NoodleThe Retirement Answer ManKaiser Family Foundation (KFF)Healthcare.govDefine Financial- Taylor SchulteStay Wealthy Retirement Show- Taylor Schulte (podcast)

Roger Whitney continues the four-part series on navigating health care before Medicare, focusing this week on controlling costs—both through everyday decisions and by understanding how the Affordable Care Act (ACA) subsidy system works now that the expanded credits have expired. He explains the return of the 400% federal poverty level “cliff,” walks through how modified adjusted gross income (MAGI) impacts premiums, shares listener experiences with inflation and subsidy loss, and explores the ethical tension around optimizing for government benefits.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 week three of the four-part series on health care before Medicare, focusing on controlling health care costs and understanding ACA subsidies. He previews next week’s structured decision framework and conversation with Taylor Schulte of Define Financial.PRACTICAL PLANNING SEGMENT(02:35) Start with the fundamentals: staying or getting healthy through strength, cardio, mobility, screenings, and proactive chronic condition management to potentially reduce long-term costs.(04:58) Compare all available coverage options and use practical strategies like staying in-network, timing procedures, and shopping prescriptions to manage costs.UNDERSTANDING THE ACA SUBSIDY SCHEME (POST-2025 CHANGES)(08:48) Roger breaks down the Affordable Care Act’s premium subsidy scheme, designed to make health care more affordable and protect coverage for preexisting conditions. He explains how subsidies are based on income relative to the federal poverty level (FPL) and how the rules have changed over time, including expansions under the American Rescue Plan and temporary extensions during COVID.(11:55) Roger explains how the premium tax credit works, including that eligibility is based on having income between 100% and 400% of the federal poverty level, and that exceeding the threshold by even $1 eliminates any subsidies(14:00) Roger gives an example of a married couple comparing higher versus lower income, illustrating how managing income can significantly affect subsidies in the years before Medicare.(15:47) What counts toward Modified Adjusted Gross Income (MAGI) and what does not count.(18:00) Reconciliation risk: estimating income during open enrollment and potentially repaying subsidies if actual income exceeds projections.(22:30) Strategic planning opportunities: building tax diversification before retirement (taxable, Roth, HSA) to create flexibility in managing MAGI and avoiding unforced errors like unexpected capital gain distributions, RSU vesting, or inherited IRA withdrawals.(26:40) Common pitfalls that can unexpectedly reduce your health care subsidies, and why keeping a buffer below the income cliff matters.LISTENER QUESTIONS & OBSERVATIONS(30:25) Joe reflects on retiring in his early 50s and how health care costs quickly became a major factor in his retirement planning.(35:35) Clarification on ACA navigators and where to find assistance through HealthCare.gov and research from Kaiser Family Foundation.(37:00) David shares his experience navigating insurance before Medicare, highlighting how exploring different options helped manage costs.(38:36) Gene asks about handling a gap in coverage before Medicare, and Roger shares strategies to manage costs and explore available options.(45:20) Philosophical discussion on whether it is appropriate to intentionally manage income to qualify for subsidies, and how each person must reconcile financial optimization with personal values.SMART SPRINT(51:30) Choose one area of spending this week—health care or otherwise—and apply intentional cost awareness to build the habit of conscious cost control.REFERENCESSubmit a Question for RogerSign up for The NoodleThe Retirement Answer ManKaiser Family Foundation (KFF)Healthcare.gov

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 clarity, confidence, and comfort to lean in and rock it.(00:30) Roger introduces week two of the four-part series on health care before Medicare and explains why assumptions about health care costs can shut down curiosity, create false tradeoffs, and delay retirement decisions.PRACTICAL PLANNING SEGMENT(05:05) After last week’s sticker shock, Roger shifts the focus to observing health care options before tackling cost mitigation next week.(05:28) Option #1 — COBRA: how continuation coverage works, who qualifies, how long it lasts, and why it can serve as a temporary bridge despite higher costs.(12:35) Option #2 — Affordable Care Act (ACA): marketplace coverage, guaranteed issue for preexisting conditions, plan tiers, and why the system is complex but flexible.(19:46) Option #3 — Part-time employer coverage: using part-time work to access group insurance, earn income, and maintain purpose and social connection.(25:20) Other alternatives, including private non-marketplace plans and health share plans, and why they require caution.LISTENER QUESTIONS(28:19) Joni asks about creating a trust will instead of a straight will, naming her son as beneficiary, and how traditional and Roth IRAs would be distributed under SECURE Act rules.(34:42) Christine asks whether it’s possible to anticipate capital gains distributions in open-end mutual funds before year-end.(38:45) Andy shares an observation about Monte Carlo simulations.SMART SPRINT(42:20) Roger encourages listeners to identify and challenge their assumptions about health care and retirement timing.REFERENCESSubmit a Question for RogerSign up for The NoodleThe Retirement Answer ManKaiser Family Foundation (KFF)Healthcare.gov

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.REFERENCESSubmit a Question for RogerSign up for The NoodleThe Retirement Answer ManKaiser 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.RESOURCESSign up for our next webinar!Submit a Question for RogerSign up for The NoodleThe 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.REFERENCESSign up for our next webinar!Submit a Question for RogerSign up for The NoodleThe 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.REFERENCESSign up for our next webinar!Submit a Question for RogerSign up for The NoodleThe 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.REFERENCESSubmit a Question for RogerSign up for The NoodleThe Retirement Answer ManLivewithroger.comThe 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.REFERENCESSubmit a Question for RogerSign up for The NoodleThe Retirement Answer ManFinancial 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.REFERENCESSubmit a Question for RogerSign up for The NoodleThe 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.REFERENCESSubmit a Question for RogerSign up for The NoodleThe 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. REFERENCESSubmit a Question for RogerSign up for The NoodleThe Retirement Answer Man

💬 Show NotesIn 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.REFERENCES1984- George OrwellSubmit a Question for RogerSign up for The NoodleThe Retirement Answer Man

💬 Show NotesIn this Thanksgiving Eve episode, Roger Whitney encourages listeners to carry gratitude into everyday life, emphasizing the value of recognizing specific moments and taking “mental snapshots” of what matters. He also addresses common retirement questions, including how to think about traditional versus Roth IRAs and whether to use IRA withdrawals or pursue Roth conversions. It’s a clear, practical discussion to help you reflect and make informed planning decisions.OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN(00:00) This show is dedicated to helping you rock retirement (00:40) Roger reflects on thankfulness and gratitude.RETIREMENT TOOLKIT(08:33) Roger gives a quick refresher on the three main types of accounts used in retirement planning and how each is treated for tax purposes.LISTENER QUESTIONS(14:16) Roger walks through how to approach the common dilemma of using a traditional IRA for living expenses versus doing Roth conversions. (26:49) Dominic asks why qualified charitable distributions can’t be used to fund a donor-advised fund, even though the donation is tax-deductible.(30:31) BB and Shell ask whether contributing to a Roth versus traditional 403(b) and 457 plans makes sense given their high current tax rate and plans to retire and move to a lower- or no-tax state.SMART SPRINT(34:35) This week’s Smart Sprint challenges listeners to make thankfulness meaningful by telling someone specifically why they are grateful for them.CLOSING THOUGHTS(35:18) Roger shares his gratitude for listeners and feedback, acknowledges the complexity of retirement planning, and emphasizes his commitment to providing actionable advice while reminding everyone it’s okay not to have all the answers.REFERENCESSubmit a Question for RogerSign up for The NoodleThe Retirement Answer Man

💬 Show NotesIn this episode, Roger Whitney dives into the essentials of required minimum distributions, explaining the age thresholds, how the amounts are calculated using IRS life expectancy tables, and how to manage multiple IRAs and 401(k)s. He also answers listener questions, including whether a flexible premium deferred income annuity might make sense and how to determine how much you can safely give to loved ones or charity now. Packed with practical advice and actionable insights, this episode helps listeners navigate the rules and strategies that can impact their retirement planning.OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN(00:00) This show is dedicated to helping you have the confidence to rock retirement.THE RETIREMENT TOOLBOX(01:18) In this Retirement Toolbox segment, we take a timely look at required minimum distributions—what they are and how they work for the accounts you own.(03:22) A quick breakdown of the current IRS rules for required minimum distributions, outlining the different start ages based on your birth year.(05:22) How RMDs are calculated using your year-end balance and IRS life expectancy tables.(08:30) When should you take your money out, and what happens if you don’t?(10:48) How to handle RMDs across multiple IRAs and 401(k)s and why long-term planning and account consolidation matter.(14:00) What are some strategies to minimize or mitigate your future required minimum distributions?LISTENER QUESTIONS(15:23) Submit your questions through AskRoger.me, and we’ll help you take a baby step toward a rock-solid retirement.(15:54) Our title question comes from Rich, who asks if a flexible premium deferred income annuity would be a good idea given his retirement savings, Social Security, pension, and minimal debt.(27:14) A listener asks how to determine how much they can safely give to loved ones or charity now, rather than leaving it as an inheritance later.SMART SPRINT(33:22) In the next seven days, estimate your future RMD—even if it’s 10 years away—assuming your IRA or 401(k) grows at a reasonable rate.CLOSING THOUGHTS(34:04) An update on the merger of Tanya Nichols’ and Roger’s advisory firms, with a new unified brand—Retire Agile—coming in 2026 and opportunities for client feedback on branding and design.REFERENCESSubmit a Question for RogerSign up for The NoodleThe Retirement Answer ManSchwab RMD CalculatorFidelity RMD Calculator

💬 Show NotesIn this episode, Roger Whitney explores the psychology of loss aversion and how it affects financial decision-making. He introduces the new Retirement Toolbox segment, offering practical, actionable tools to help you strengthen your retirement plan. We also cover the benefits of Qualified Charitable Distributions and answer listener questions on retirement planning and asset allocation. Don’t miss this insightful discussion designed to help you confidently navigate and optimize your retirement!OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN(00:00) This show is dedicated to helping you not just survive retirement, but rock itPRACTICAL PLANNING SEGMENT(01:00) Roger breaks down loss aversion and how it relates to retirement.THE RETIREMENT TOOLBOX(04:35) Roger launches a new segment on essential financial tools, starting with the Qualified Charitable Distribution, a timely, tax-smart way to give at year-end.LISTENER QUESTIONS(11:53) Wes asks how to build retirement reserves before retirement without triggering higher taxes.(17:12) Roger responds to John’s critique of the “Process Over Panic” episode, clarifying why a retirement plan should be treated as a living, flexible guide rather than a rigid set of rules.(22:52) Feedback from David highlights why factoring early losses in Monte Carlo simulations can boost confidence despite slight double-counting.(26:35) Thoughtful listener disagreements are welcomed as a way to deepen understanding and improve retirement planning insights.(27:43) Thomas has some questions about getting started with a retirement planner.SMART SPRINT(36:07) In the next seven days, anyone within three years of retirement should map out their liquidity and consider reallocating assets to protect against market swings in the early years, avoiding unnecessary risk if funds will be needed soon.CLOSING THOUGHTS(37:05) I've been building a personal library of classics, including fiction and nonfiction, and welcome book suggestions via The Noodle to help expand the reading list.REFERENCESSubmit a Question for RogerSign up for The NoodleThe Retirement Answer ManThinking, Fast and Slow- Daniel Kahneman

💬 SHOW NOTESIn this episode, Roger Whitney explores the art of retirement goal setting with his signature blend of practical advice and thoughtful reflection. He sits down with Cesar Aguirre, who shares how leaving a corporate career led to a purposeful and fulfilling retirement, the evolution of his book, and the importance of aligning goals with personal values rather than just chasing big achievements. Roger also addresses listener questions on planning, discretionary spending, and shifting mindsets around money, offering actionable insights to help create a retirement that’s intentional, joyful, and aligned with personal values.OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN(00:00) This show is dedicated to helping you not just survive retirement, but rock it(01:07) The cost-of-living adjustment for Social Security was announced.ROCKIN’ RETIREMENT IN THE WILD WITH CESAR AGUIRRE(02:05) Roger talks with Cesar about his book and how he is rockin’ retirement.(02:41) Roger introduces Cesar Aguirre, author of Retirement with Purpose: The 10 R's for a Joyful Retirement.(05:55) At 65, Cesar realized many people approached retirement without a plan, inspiring him to document his process so others could find structure and clarity in their own journey.(08:35) The pandemic slowed Cesar’s busy career, prompting him to shift from focusing on leaving work to discovering what he was retiring to.(11:35) Cesar shares how a five-year assignment abroad led to a permanent move to the U.S. in the early ’90s, marking a pivotal shift in his life and career.(12:25) Cesar reflects on cultural views of retirement, blending Mexico’s family-centered “jubilación” with the U.S. ideal of independence to create a more balanced, proactive approach to this new season of life.(14:51) There are 10 R’s in the book, starting with Review.(17:25) Roger asks Cesar how to answer the question, “What do I want?”(20:17) Cesar explains that creating his book with a service purpose removed pressure, letting him focus on making it useful, reach a broader audience, and now develop a Spanish edition.(21:56) Cesar encourages newly retired listeners to create structure, revisit plans, and embrace retirement as a journey with purpose.LISTENER QUESTIONS(24:18) In an audio question, Gary, who will retire in 2026, shares how managing “old” retirement savings feels different from spending a paycheck and asks for guidance on navigating this shift in mindset.(33:56) A listener, who chose to remain anonymous, asks how to distinguish between the essentials of a “base great life” and the discretionary spending that falls into the “wants” category.’(35:55) A listener praised Roger’s shift from chasing big goals to focusing on values and creating conditions to explore life personally and meaningfully.(38:20) Dennis asks about the Retirement Podcast Network, and Roger explains that while it’s still active, he and Taylor Schulte decided to prioritize other projects and let this one remain on the back burner.SMART SPRINT(40:01) In the next seven days, reflect on the phrase, “you can’t take it with you.”BONUS(41:03) In this wrap-up, Roger addresses listener feedback from a past episode on organic food.REFERENCESSubmit a Question for RogerSign up for The NoodleThe Retirement Answer ManRetirement With Purpose: The 10 R's for a Joyful Retirement: A practical and thoughtful guide to rediscovering yourself and flourishing in the retirement stage.- Cesar Aguirre

💬 Show Notes In this episode, Roger Whitney wraps up our four-week series on smarter retirement goal setting. He dives into the ideas of buoyancy and Maslow’s hierarchy of needs, showing how they play a role in planning a retirement that actually works for you. Using two relatable avatars – the Grinder and the Dreamer – Roger shares practical, real-world strategies to help navigate the twists and turns of retirement planning. Tune in for insights that will help you make your retirement not just secure, but truly rock! OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN(00:00) This is the last of a four-week series on better retirement goal settingPRACTICAL PLANNING SEGMENT(01:58) The first concept for today is the concept of buoyancy.(04:50) Roger talks about Maslow’s hierarchy of needs.(07:50) A look inside the Advice Lab Roger runs with his work team.AVATAR CASE STUDY- THE GRINDER AND THE DREAMER(10:10) Introduction of two avatars created by the team — the Grinder and the Dreamer.(10:58) First, Roger breaks down the Grinder.(14:27) What are triggers that might help a grinder reevaluate retirement planning?(16:57) What do Grinders crave?(18:50) How do you navigate as a Grinder or as someone in a relationship with a Grinder?(21:50) The pillars of retirement are a helpful framework when it comes to Grinders.(27:00) Next, Roger breaks down the avatar of the Dreamer.(29:30) What are the triggers that a Dreamer faces?(32:30) Roger breaks down the retirement pillars for Dreamers.(37:00) Roger reflects on how his partnership with Tanya mirrors the Dreamer and Grinder archetypes, showing how balancing vision and execution can lead to better communication and more effective retirement goals.LISTENER QUESTIONS(38:14) You can submit questions at AskRoger.me(38:40) Barbara shares thoughts on a recent episode.(42:04) Roger shares an audio clip from Tom.(44:27) One listener shares that drawing down the accounts is a mental challenge.(45:49) Rod asks what portion of a 71-year-old’s $5–6M retirement portfolio could go into low-risk private credit.SMART SPRINT(48:38) In the next seven days, reflect on where you fall between Dreamer and Grinder and consider that when setting or refreshing your retirement goals, so you can better balance your approach.REFERENCESSign up for our next Webinar!Submit a Question for RogerSign up for The NoodleThe Retirement Answer ManMaslow's Hierarchy of Needs

💬 Show NotesIn this episode, we continue our four-week series on better retirement goal setting with Roger Whitney. This week, we delve into the dynamics of navigating retirement goals as life unfolds and the concept of opportunity cost. In the second half, Roger has enlightening discussion with Dr. Bobby, where he explores the pros and cons of organic food and its relevance to our health and finances. Discover how to align your retirement goals with your evolving self and make informed choices about your lifestyle. Tune in for practical insights that can help you rock your retirement!OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN(00:00) This is week three of a four-week series on better retirement goal setting, plus Roger chats with Dr. Bobby about the cost-benefit of buying organic.(02:55) Roger encourages registration for his next live meetup at livewithroger.com.PRACTICAL PLANNING SEGMENT(03:40) Roger reflects on setting goals that will align with the current version of you and also who you are becoming.(05:44) Roger explores how goals evolve over time, the barriers that make it hard to recognize and adapt to those changes, and a simple protocol to help ensure your goals stay aligned with what matters most.(07:15) Priorities shift over time as what once mattered may lose importance and new values emerge.(10:27) Life events like health changes, family needs, or loss can rapidly reorder goals.(12:41) Common barriers to noticing change include inattention, sunk cost fallacy, and social pressure.(16:01) Regular reflection helps keep goals aligned with what’s truly important.(20:05) Review spending regularly to ensure it reflects your current priorities.CHAT WITH DR. BOBBY(23:20) Roger introduces Dr. Bobby to talk about organic foods.(25:52) What are organic foods?(29:03) Dr. Bobby breaks down the cost of organic food.(33:00) What are the benefits of organic food? Is it worth the cost?(38:15) Roger acknowledges that some people feel strongly about buying organic as a way to take control of their health.(40:57) 80% of the US population doesn't get enough fruits and vegetables.(42:16) Dr. Bobby breaks down the ROI on buying organic.(48:23) If you do buy organic, which products should you buy?(52:20) Bobby talks about his podcast and the power of positive thinking when dealing with illness.SMART SPRINT(53:13) In the next seven days, pull out your retirement plan of record and review your goals.REFERENCES Live Long and Well with Dr. Bobby- podcastSign up for our next Webinar!Submit a Question for RogerSign up for The NoodleThe Retirement Answer Man

In this episode, Roger Whitney continues his four-week series on retirement goal setting, focusing on the importance of building agile retirement goals. He emphasizes creating the right conditions for discovering what you truly want in retirement, rather than fixating on specific desires. Roger shares insights on self-discovery, the anatomy of goals, and the significance of establishing a solid foundation for a fulfilling retirement. Tune in to learn how to navigate your retirement journey with confidence and purpose!OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN(00:00) This week Roger talks about building agile retirement goals.PRACTICAL PLANNING SEGMENT(03:10) The intent is to build goals that are more meaningful to you so you can rock retirement.(07:00) How do you set goals that are meaningful to you in an agile way?(07:39) You want to start with self-discovery and establishing or revisiting your values.(09:53) Focus on creating conditions to explore your values and build a life where fulfillment naturally follows. (13:43) You have to experiment to determine what is right for you.(18:30) Roger talks about the anatomy of a goal, specifically low stakes goals that maximize optionality in retirement planning.(21:08) Roger talks about high stakes goals.(25:04) Low-stakes goals help you experiment, make confident decisions, and discover what truly supports a fulfilling retirement. LISTENER QUESTIONS(27:30) Roger answers Melissa’s questions about rolling over an IRA without penalty and whether to trust a flat-fee fiduciary firm that offers to manage her accounts. (33:06) Greg asks Roger to revisit healthcare before Medicare. (34:17) Rob asks about deferring Social Security to age 70 and whether he still receives COLA increases in addition to the 8% delayed retirement credit.(36:03) Chris asks about using only a total world stock and bond index for his portfolio.(40:20) Roger advises keeping a local contingency fund so you always have accessible cash and don’t feel “cash poor.”SMART SPRINT(43:20) Go back to your retirement goals and the plan you’ve put together. Look at them through the lens of our recent discussionRESOURCESSign up for our next Webinar!Scarcity Brain: Fix Your Craving Mindset and Rewire Your Habits to Thrive with Enough- Michael EasterSubmit a Question for RogerSign up for The NoodleFOLLOW US ON SOCIALSFollow Us on Facebook!Follow Us on Instagram