# Healthcare Before Medicare: Creating Your Own Action Plan

Page: https://stenobird.com/podcast/retirement-answer-man-391124/healthcare-before-medicare-creating-your-own-action-plan
Text version: https://stenobird.com/podcast/retirement-answer-man-391124/healthcare-before-medicare-creating-your-own-action-plan.md
Podcast: [Retirement Answer Man](https://stenobird.com/podcast/retirement-answer-man-391124)
Published: 2026-02-25T09:00:00+00:00
Episode link: https://share.transistor.fm/s/f17a945d
Audio file: https://media.transistor.fm/f17a945d/075b15be.mp3
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JSON: https://stenobird.com/v1/public/podcasts/retirement-answer-man-391124/episodes/healthcare-before-medicare-creating-your-own-action-plan
Duration seconds: 2756

## Resource

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, continuity of care, and complexity. (03:30) Roger talks about avoiding unforced errors that could cost you money, disrupt care, or create unnecessary stress. (05:18) Roger introduces the OODA Loop—observe, orient, decide, act—as a practical way to think step by step about health coverage choices. (05:52) Observe: Build a 5-year retirement income and spending plan, estimate taxes and MAGI, identify where you fall relative to the ACA subsidy cliff, and review withdrawal sources (taxable, pre-tax, Roth) along with future RMD implications. (14:21) Orient: Clarify what matters most to help you make a…

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## Transcript

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