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