Retirement Answer Man

Roger Whitney, CFP®, CIMA®, RMA, CPWA®
  • 0.0 (0)
  • INVESTING
  • UPDATED WEEKLY

A top retirement podcast. Roger Whitney, CFP®, CIMA®, CPWA®, RMA, guides you on how to actually do retirement well financially and personally. This retirement podcast isn't afraid to talk about the softer side of retirement. It will teach you how to retire with confidence. Two-time PLUTUS winner for best retirement podcast / blog and the 2019 winner for best financial planner blog. This retirement podcast covers how to create a paycheck, medicare, healthcare, Social Security, tax management in retirement as well as retirement travel and other non-financial issues you'll need to address to rock retirement. Retirement isn’t an age OR a financial number. It’s finding that balance between living well today and feeling confident about your retirement. It’s about gaining more freedom to pursue the life you want. Join the rock retirement community at www.rogerwhitney.com

  1. Healthcare Before Medicare: How to Lower Your Costs

    22 HR AGO

    Healthcare Before Medicare: How to Lower Your Costs

    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.REFERENCES Submit a Question for RogerSign up for The NoodleThe Retirement Answer ManKaiser Family Foundation (KFF)Healthcare.gov

    53 min
  2. Healthcare Before Medicare: Your Options

    11 FEB

    Healthcare Before Medicare: Your Options

    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.REFERENCES Submit a Question for RogerSign up for The NoodleThe Retirement Answer ManKaiser Family Foundation (KFF)Healthcare.gov

    45 min
  3. Healthcare Before Medicare: What Happens When You Retire Before 65?

    4 FEB

    Healthcare Before Medicare: What Happens When You Retire Before 65?

    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 RogerSign up for The NoodleThe Retirement Answer ManKaiser Family Foundation (KFF)Healthcare.gov

    42 min
  4. Retire on FIRE: Rocking an Early Retirement- The Challenges of Retiring Early

    28 JAN

    Retire on FIRE: Rocking an Early Retirement- The Challenges of Retiring Early

    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 RogerSign up for The NoodleThe Retirement Answer Man

    28 min
  5. Retire on FIRE: Rocking an Early Retirement- Henry and Lucy's Resources

    21 JAN

    Retire on FIRE: Rocking an Early Retirement- Henry and Lucy's Resources

    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 RogerSign up for The NoodleThe Retirement Answer Man

    48 min
  6. Retire on Fire- Rocking an Early Retirement: Henry and Lucy's FIRE Goals

    14 JAN

    Retire on Fire- Rocking an Early Retirement: Henry and Lucy's FIRE Goals

    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 RogerSign up for The NoodleThe Retirement Answer Man

    54 min
  7. Retire on FIRE- Rocking an Early Retirement: Meet Henry and Lucy

    7 JAN

    Retire on FIRE- Rocking an Early Retirement: Meet Henry and Lucy

    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 RogerSign up for The NoodleThe Retirement Answer ManLivewithroger.comThe Millionaire Next Door: The Surprising Secrets of America's Wealthy- Thomas J Stanley, Ph.D.

    50 min
  8. Year-End Planning: Estimated Tax Payments

    31/12/2025

    Year-End Planning: Estimated Tax Payments

    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 RogerSign up for The NoodleThe Retirement Answer ManFinancial Calculators from Dinkytown.net

    38 min
See All (637)

Hosts & Guests

About

A top retirement podcast. Roger Whitney, CFP®, CIMA®, CPWA®, RMA, guides you on how to actually do retirement well financially and personally. This retirement podcast isn't afraid to talk about the softer side of retirement. It will teach you how to retire with confidence. Two-time PLUTUS winner for best retirement podcast / blog and the 2019 winner for best financial planner blog. This retirement podcast covers how to create a paycheck, medicare, healthcare, Social Security, tax management in retirement as well as retirement travel and other non-financial issues you'll need to address to rock retirement. Retirement isn’t an age OR a financial number. It’s finding that balance between living well today and feeling confident about your retirement. It’s about gaining more freedom to pursue the life you want. Join the rock retirement community at www.rogerwhitney.com

Information

  • Creator
    Roger Whitney, CFP®, CIMA®, RMA, CPWA®
  • Years Active
    2014 - 2026
  • Episodes
    637
  • Rating
    Clean
  • Copyright
    © Roger Whitney, 2024
  • Show Website
    Retirement Answer Man

You Might Also Like