Healthcare Before Medicare: Creating Your Own Action Plan

From Retirement Answer Man by Roger Whitney, CFP®, CIMA®, RMA, CPWA®

February 25, 2026 · 46 min · Episode 632

About this episode

Roger Whitney concludes a series on healthcare before Medicare, introducing a decision-making framework and discussing various coverage options with guest Taylor Schulte.

Roger Whitney wraps up the four-part series on navigating health care before Medicare by introducing a practical decision-making framework using the OODA Loop—observe, orient, decide, act—to help you avoid unforced errors and make a confident judgment call. He walks through organizing your retirement cash flow, estimating MAGI and ACA subsidy eligibility, evaluating COBRA, ACA, and private coverage options, and weighing tax optimization against simplicity and continuity of care. He’s joined by Taylor Schulte of Define Financial to discuss how professionals navigate Roth conversions, Social Security timing, ACA cliffs, and the trade-offs between optimizing for subsidies versus long-term tax planning. 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 final week of the health care before Medicare series and previews upcoming episodes with Harry Reese (co-author of How to Feel Loved) and retirement researcher Wade Pfau. PRACTICAL PLANNING SEGMENT (02:30) Roger reviews the three “heads” that must be managed before Medicare- cost…

People in this episode

Host: Roger Whitney

Guest: Taylor Schulte

Topics covered

healthcare planning
Medicare
retirement cash flow
tax optimization
insurance options
decision-making framework

Keywords

OODA Loop
MAGI
ACA subsidy
COBRA
Roth conversions
Social Security timing
health coverage choices

Mentioned in this episode

Organizations: Define Financial

Books & works: How to Feel Loved