Year-End Planning: Estimated Tax Payments

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