I want to retire at 62. What do I do about insurance until 65?

That gap is one of the most common reasons people delay retirement, and it is usually solvable. Building a plan for the least expensive appropriate coverage before 65 is part of what we do, and how your income is arranged in those years often affects what that coverage costs.

Should I buy long-term care insurance?

For some people yes, for others no. We will work through the pros and cons with you and, if you decide to pursue it, direct you to a credible agent. Since we don’t sell the policy, we have no stake in which way you land.

Will a Roth conversion increase my Medicare premiums?

It can. Premiums look back at your income from two years prior, so a conversion done today can show up as a higher premium later. It is still often worth doing. The point is to size it deliberately rather than be surprised.

A patient greeting her doctor at a medical office appointment

Medicare & Health Insurance Planning

The years between retiring and turning 65

Retire before 65 and you need coverage Medicare won’t provide yet, at a price that depends on the income your plan reports. Reach 65 and the question becomes which supplement fits. We plan for both, and we sell neither.

Retiring early is a coverage problem and an income problem

One major worry in retirement is how you’ll handle medical expenses. So whether you’re 65+ looking for the best Medicare supplement, or under age 65 looking to cut insurance costs, we can help.

What surprises people is how tightly the two are linked. What you pay for coverage before 65 depends on the income your plan reports, and what you pay for Medicare later depends on your income from two years earlier. Because we already project your income year by year, those costs are something we can plan around instead of discover.

Before 65

Medicare isn’t available yet
Coverage has to be bought, and the price depends on the income your plan reports
The goal is the least expensive coverage that is still the right coverage

65 and after

Apply for Medicare
Choose a supplement with a vetted professional
Premiums look back at your income from two years earlier

As your guide, we:

The Perennial Income Model™ helps us prepare for your future healthcare needs. As your guide, we:

Help you apply for Medicare
Align you with a vetted Medicare Supplement Professional
Create a plan so you can acquire the least expensive and best health insurance coverage prior to age 65
Consider with you the pros and cons of purchasing Long-Term Care insurance and direct you to a credible agent should you determine that this course of action suits your needs

We don’t sell insurance

That distinction matters most with long-term care, where the advice you get often depends on who profits from it.

How a Roth conversion can raise a Medicare premium

What’s included

Healthcare planning, as part of your plan

Apply for Medicare
Pre-Medicare insurance planning
Fund long-term care or disability

These pieces are not sold separately. They come together as one plan, for one transparent quarterly fee.

Questions retirees ask us about healthcare

No. We are fee-only and take no commissions on insurance. We help you apply for Medicare and align you with a vetted Medicare Supplement Professional, then stay involved while you choose.

Related webinars

Explore these sessions for deeper guidance on coordinating your retirement income plan.

The rest of your plan

No decision in retirement stands on its own. Here is how the other pieces fit together.

Don’t let health insurance decide your retirement date

If the only thing standing between you and retirement is coverage until 65, that is worth a 15-minute conversation.

Schedule a Call