Healthcare Before Medicare: Your Options

Retirement Answer Man

Roger Whitney, CFP®, CIMA®, RMA, CPWA®

Education, Investmentmanagement, Saving, Self-improvement, Careerplanning, Retirement, Business, Lifeplanning, Investing, Retirementplanning, Financialplanning, Retirementpodcast

4.6 • 1.2K Ratings

🗓️ 11 February 2026

⏱️ 45 minutes

🔗️ Recording | iTunes | RSS

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Summary

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

Transcript

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0:00.0	Recalibration of the mind means clearing our perceptions and recovering our capacity for pure observation.
0:10.1	Ichili.
0:12.2	Hey there.
0:13.0	Welcome to the show dedicated to helping you have the clarity so you have the comfort and the confidence to lean into your own retirement and make the most of it.
0:23.0	My name is Roger Whitney.
0:24.7	I'm honored to be here with you today.
0:27.8	Today is our second of a month-long series on navigating health care before Medicare.
0:37.3	And filling that gap so we don't miss our life unintentionally.
0:42.1	And today what we're going to do is observe what our options are for health care if we're not
0:50.0	yet 65. Last week, we sort of shocked ourselves with the cost, and that was intentional because we have a
0:58.5	lot of money.
1:00.0	There are a lot of disruption to your life with health care, but that doesn't mean that you
1:06.1	can't navigate it.
1:08.5	And so today we're going to do some observing of what the options are. And next week,
1:12.3	we'll talk about strategies around income and to manage that cost. And then in the last
1:18.6	episode of this month, we'll try to put it all together to give you a basic game plan or framework
1:24.4	to think through it. Observing can be hard because of assumptions.
1:33.0	I heard a great quote related to relationships, but I think it was Henry Winkler the other day.
1:38.7	Assumptions are the termites of relationships. That's a good one. Assumptions are bigger than termites when it comes to
1:49.6	decision making. When we make assumptions about the cost of health care or our options based off
1:57.7	of our previous experience, maybe four, five, ten years ago, the news or articles
2:05.5	that we've read or videos that we've watched. When we make assumptions on very incomplete
	...

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