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You have $1M or more invested. Retirement is 1 to 8 years away. But one question keeps coming up: what do you do about health insurance?
The question nobody prepared you for: what happens to your health insurance between the day you retire and the day Medicare starts at 65.
Serving families across Virginia from offices in Staunton, Harrisonburg, Charlottesville, and Winchester.
You've done the right things.
Saved consistently. Maxed the 401k. Lived below your means for decades.
But every time retirement comes up, the same question stops the conversation cold:
What do we do about health insurance?
COBRA sounds expensive. ACA sounds complicated. And you've heard stories about people who got the math wrong and paid for it for years.
Here's what most people don't know: there's a window between retirement and Medicare where the decisions you make about income can determine whether you qualify for subsidies worth thousands of dollars per year, or pay full price for coverage you didn't have to.
Planning is what separates the people who get this right from the people who find out the hard way at 63.
Most advisors don't touch this. Most CPAs don't either. It falls through the cracks between the people who are supposed to be helping you.
WHO WE ARE
Middlebrook Wealth works with Virginia families who have been doing everything right and want to make sure they don't undo it with one bad decision at the finish line.
Our team includes CFP and CEPA certified advisors who coordinate your financial plan, your CPA, and your attorney together. Not in silos. One team that makes sure nothing falls through the cracks.
Healthcare planning has been the number one driver of new clients for this firm for three years running. Not because we do something exotic. Because most people have never had anyone walk them through the math.
We can't help everyone. If you want to manage every detail yourself, we're not your firm. But if you want a team that runs the numbers on COBRA vs. ACA, shows you where subsidies may apply, and builds a retirement income plan designed around keeping your healthcare costs as low as possible, that's what we do.
Frequently Asked Questions
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You have a few paths and they cost very different amounts. COBRA continues your current employer plan for up to eighteen months, at the full premium plus a fee. An ACA marketplace plan usually costs less and may come with a narrower network. If your spouse is still working, joining their plan is often the cheapest option and the one people overlook. Which one wins depends on your doctors, your prescriptions, how many years you need to cover, and how much control you have over your taxable income.
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COBRA makes sense when you are mid-treatment, when you have met your deductible for the year, or when your doctors are the deciding factor. Marketplace plans tend to win on cost, especially for households who can manage their income to qualify for premium tax credits. The comparison changes year by year, so retiring in March produces a different answer than retiring in October.
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Marketplace premium tax credits are calculated from your modified adjusted gross income. Because you decide which accounts to draw from in early retirement, you have more control over that number than you did while working. Drawing from a taxable brokerage account, a Roth, and a traditional IRA produces different income totals for the same amount of spending money, and that difference can change your premium substantially.
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IRMAA is a surcharge on Medicare Part B and Part D premiums for higher income households. Medicare looks at your income from two years prior, which means your income at 63 sets your Medicare premium at 65. This catches people who do large Roth conversions in their early sixties without accounting for what it does to their Medicare costs later.
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Often yes, and the timing matters more than the amount. The window between retiring and starting Social Security is usually when your taxable income is lowest, which makes conversions cheapest. The complication is that conversion income can reduce your marketplace subsidy in the same year and raise your Medicare premium two years later. The right answer balances all three.
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Medicare eligibility before 65 is limited to specific circumstances involving disability or certain diagnoses. For most people retiring early, the answer is no, and the years between your retirement date and your 65th birthday need to be planned for.
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More than most people expect, and the range is wide. Two households retiring the same year with the same portfolio can pay very different amounts depending on their income planning, their state, their ages, and whether they qualify for premium tax credits. We price it against your actual situation rather than a national average, because averages are not useful when the spread is this large.
OUR STRATEGY
A Plan That Covers Every Corner of Your Financial Life
Retirement is not a finish line. It is a transition into the life you have been building. At Middlebrook Wealth, we build a comprehensive strategy around your income, healthcare, taxes, and investments, that is coordinated, not managed in silos. We look at the full picture to determine when you can retire, how to make your money last, and identify roadblocks. No two retirements look the same, so every plan we build is specific to you, and built to evolve as your life does.
Income Strategies
It's not just about what you've saved. It's about drawing from the right sources, in the right order, to minimize taxes and protect your assets long term.
Healthcare Bridge Planning
Retiring before 65 means bridging the gap to Medicare. We map your coverage options and build the cost into your plan.
Tax Location Optimization
It's not about paying the lowest taxes this year. It's about paying the lowest taxes over your lifetime.
OUR PROCESS
Planning your financial journey starts here.
Step One
We listen.
We start with an in-depth conversation to understand your income, your accounts, your timeline, and what retirement looks like for you.
Step Two
We plan.
We build a customized retirement strategy around your tax situation, healthcare costs, and investments. We design a plan to close the gap between where you are now and when you're ready to retire.
Step Three
We manage.
We put the plan in motion and actively monitor progress, adjusting your strategy as tax laws change and you approach retirement.
Ready to get started?
Reach out to our team today.
CONTACT US
Get clarity on your Retirement Plan.
Your retirement plan is about more than hitting an arbitrary number. It should reflect the life you want to live and make sure your finances are ready to support it.