Retirement Answer Man

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

As the Retirement Plan Live series wraps up, Roger Whitney shares wisdom from retirees further along the path to help Henry and Lucy think beyond the numbers. Listeners in their 50s, 60s, and 70s reflect on purpose, work, health, money, and joy—offering perspective on what really matters when retiring early. Roger closes with his own observations from decades of coaching, a Smart Sprint focused on learning from others, and listener-submitted words for the year.
OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN
(00:00) This show is dedicated to helping you not just survive retirement, but to have the confidence to lean in and rock it.
(01:33) Two announcements: next month starts a healthcare-before-Medicare series and the listener survey in The Noodle is coming soon.
WISDOM FROM RETIREES FURTHER ALONG
(03:41) Roger reads listener reflections from retirees further along, sharing lessons on purpose, work, health, flexibility, and building a meaningful retirement.
ROGER’S OBSERVATIONS 
(12:54) Roger shares his observations from decades of coaching on what leads to a fulfilling retirement, including permission, projects, community, service, and avoiding distraction or scarcity thinking.
SMART SPRINT
(22:12) Identify one challenge you’re facing and talk with someone who has already walked that path—before turning to books or the internet.
LISTENER WORDS FOR THE YEAR
(25:10) Roger shares listener words for the year and the personal meaning behind them.
RESOURCES
Sign up for our next webinar!
Submit a Question for Roger
Sign up for The Noodle
The Retirement Answer Man

As the Retirement Plan Live case study continues, Roger Whitney helps Henry and Lucy move from dreaming to feasibility, organizing the real financial resources available to support an early retirement in their 40s. This episode centers on trade-offs, confidence, and the reality of giving up earned income decades early. Roger and the couple walk through income assumptions, assets, and risk tolerance before closing with listener advice, a Smart Sprint, and words for the year.
OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN
(00:00) This show is dedicated to helping you not just survive retirement, but to have the confidence and comfort to lean in and rock retirement.
(00:27) Roger introduces Week 3 of the Retirement Plan Live case study with Henry and Lucy.
(02:15) What are Henry and Lucy giving up to retire early?
RETIREMENT PLAN LIVE
(05:00) Roger asks Henry and Lucy if they pick a word of the year.
(06:05) Henry and Lucy reflect on why retiring even one year earlier feels uncomfortable without proof.
(10:50) Review of Social Security assumptions and why it’s excluded from their base plan.
(14:13) Confirmation that the plan assumes no earned income after retirement.
(20:40) Overview of after-tax assets, cash buckets, and sinking funds.
(26:20) Review of retirement accounts, savings rates, and long-term strategy.
(31:30) Home equity, college savings, and inheritance assumptions.
(33:40) Clarifying the goal for the after-tax bridge bucket.
ADVICE FROM A RETIREE
(38:39) Listener Bonnie shares an alternative approach using sabbaticals and flexible work.
(41:10) Roger reflects on optionality, skill relevance, and maintaining professional networks.

SMART SPRINT
(42:30) Roger encourages listeners to organize or update their net worth statement.
WORD FOR THE YEAR
(43:40) Listener Alex shares his word for the year: Healing.
(45:10) Listener Valerie shares her word for the year: Minimize.

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

As the Retirement Plan Live case study continues, Roger Whitney helps Henry and Lucy articulate what they want their FIRE retirement to actually look like—starting with values, dreaming without constraint, and then translating that vision into concrete goals. Along the way, Roger shares wisdom from older retirees about purpose, productivity, and flexibility, invites listeners to reflect on their own “magic,” and closes with a Smart Sprint and listener-submitted words for the year.
OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN
(00:00) This show is dedicated to helping you not just survive retirement, but to have the confidence and clarity to lean in and rock it.
(00:23) Roger previews today’s focus: Henry and Lucy’s retirement goals, advice from seasoned retirees, a Smart Sprint, and listener words for the year.
(01:00) Roger explains why retirement planning should begin with dreaming big—starting with “everything” before testing feasibility.
RETIREMENT PLAN LIVE
(03:25) Henry and Lucy walk through their core values and how those values shape their vision for retirement.
(05:55) Roger reviews and discusses Lucy’s top ten values.
(09:29) Henry talks about his top values.
(11:40) Roger reflects on whether retiring early means “burying” one’s gifts, and considers how purpose and contribution can take many forms beyond traditional work.
(13:44) Roger talks through Henry and Lucy’s goals for retirement and their budget for a great base life.
(19:47) Lucy breaks down her thought process on her great base life budget.
(23:00) Henry weighs in with his thoughts on their great base life.
(24:05) They review discretionary goals such as travel, a camper van, hobbies, and future family commitments.
(27:55) Lucy and Henry talk about aspirational wishes.
(35:00) Lucy talks about how they react during uncertain times.
WISDOM FROM RETIREES FURTHER ALONG
(41:41) Listener Mike shares why he chose “FILE” (Financially Independent, Living Early) instead of full FIRE, emphasizing purpose and reduced stress.
(45:10) Listener Renee offers perspective on flexibility, one spouse stepping away from work, and how lower stress improved family life.
SMART SPRINT
(48:08) Roger encourages listeners to separately write down their own “magic” retirement goals—without self-editing—then share and discuss them with their partner.
WORD FOR THE YEAR
(50:07) Roger shares listener words for the year.
CLOSING THOUGHTS
(53:17) Roger previews next week’s episode, where Henry and Lucy’s assets and resources will be evaluated to see what is feasible.
REFERENCES
Sign up for our next webinar!
Submit a Question for Roger
Sign up for The Noodle
The Retirement Answer Man