Healthcare Before Medicare: Creating Your Own Action Plan

Feb 25, 2026

Taylor Schulte, retirement planner and founder of Define Financial who focuses on retirement healthcare and tax strategies. They discuss using a step-by-step OODA framework to organize five-year cashflow and MAGI estimates. Short-term bridges like COBRA, ACA cliffs, and trade-offs between Roth conversions, Social Security timing, and simplicity get practical attention.

Ask episode

AI Snips

Chapters

Books

Transcript

Episode notes

ADVICE

Build A Five Year Cash Flow Plan

Build a five-year retirement cash-flow showing income, expenses, and rough tax estimates to estimate MAGI for ACA decisions.
Map year-by-year withdrawals from after-tax, pre-tax, and Roth accounts so you can see how IRA pulls affect subsidies and premiums.

ADVICE

Inventory Your Healthcare Options

Inventory healthcare options: assess health status, providers, COBRA details, ACA marketplace quotes, employer retiree offers, and part-time employer plans.
Ask your doctors which insurers they accept to preserve continuity of care when shopping ACA plans.

INSIGHT

Decide What Really Matters

Orient decisions by ranking what matters: continuity of care, acceptable complexity, and willingness to experiment with funding to reach ACA cliffs.
Evaluate whether the potential premium savings justify the added complexity before changing distribution strategy.

Get the Snipd Podcast app to discover more snips from this episode

Get the app

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 decision.
(20:00) Decide & Act: Choose a direction, document your reasoning, update your plan of record, and implement the distribution strategy that supports your choice.

CONVERSATION WITH TAYLOR SCHULTE

(22:25) Roger introduces Taylor Schulte from Define Financial
(23:15) Why health care before Medicare shouldn’t automatically delay retirement and how assumptions often go untested.
(26:50) Evaluating alternatives beyond ACA, including COBRA as a short-term bridge and private plans.
(31:50) The tension between Roth conversions and ACA subsidies, and how Social Security timing affects MAGI.
(34:20) Avoiding the “optimization trap”: sometimes paying more for simplicity still results in a resilient retirement plan.
(36:40) The key takeaway is that there’s no perfect answer—retirees should explore options, make informed decisions without fear, and use healthcare planning as a tool rather than a barrier or excuse to delay retirement.

SMART SPRINT

(43:35) Set a reminder to review your health care strategy using a structured approach—especially if retirement or Medicare enrollment is approaching. The goal is to be intentional, not reactive.

REFERENCES

Submit a Question for Roger
Sign up for The Noodle
The Retirement Answer Man
Kaiser Family Foundation (KFF)
Healthcare.gov
Define Financial- Taylor Schulte
Stay Wealthy Retirement Show- Taylor Schulte (podcast)