Healthcare Before Medicare: What Happens When You Retire Before 65?
Wed Feb 04 2026
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
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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