Don’t Let December 15 Sneak By: Give Your 2026 Health Insurance a Checkup

Health insurance open enrollment doesn’t come with fireworks or confetti, but it does come with real deadlines and real money on the line.

For most people buying coverage through the Health Insurance Marketplace, enrolling or updating your plan by December 15 means your coverage will start January 1, 2026. That deadline is coming up quickly.

This is the time to pause and ask:

• What is my health insurance actually going to look like in 2026?

• Are my doctors and hospitals still covered?

• Are my prescriptions still covered the way I expect?

Each year, insurers can change what they cover, what they charge, and which providers are in-network. A plan that worked well in 2025 may quietly become more expensive, more restrictive, or simply not a good fit for the year ahead.

Don’t Just “Let It Ride”

I know it’s tempting to say, “I’ll just keep what I had last year.” The problem is that your plan may not be the same plan anymore.

From one year to the next, your insurer can change:

• Premiums: what you pay every month

• Deductibles and copays: what you pay when you use care

• Networks: which doctors, specialists, and hospitals count as in-network

• Drug coverage: which medications are covered and at what cost tier

At the same time, you may have changed too. New diagnosis, new prescriptions, new specialists, or a planned surgery can completely change what “good coverage” means for you.

A short review now can prevent a lot of stress and surprise bills later.

Planning to Retire Before 65? Health Insurance Is the Wildcard

When I talk with pre-retirees and retirees, there’s a pattern I see again and again:

Many people don’t want to work full-time all the way to 65.

Some want to fully retire in their late 50s or early 60s. Others want to shift to part-time, consulting, or something more flexible and meaningful. Emotionally and financially, they’re ready.

The wildcard is health insurance.

Medicare generally starts at 65. If you step away from an employer plan before then, you’re looking at a gap where you must cover health insurance on your own. That often means:

• Marketplace coverage (through Healthcare.gov or your state exchange)

• COBRA for a limited period

• Coverage through a spouse’s plan

• Structuring part-time work that still offers benefits

One of my clients is retiring at age 56. Together, we built a financial plan that specifically included the cost of health insurance through the Marketplace for all the years between 56 and 65. We didn’t just assume “we’ll figure it out.” We modeled different coverage options, premium ranges, and out-of-pocket costs to see what was sustainable.

That’s the real power of planning: health care stops being a vague fear and becomes a line item we can prepare for.

If you’re in your 50s or early 60s and thinking, “I don’t want to keep doing this full-time until 65,” open enrollment is a perfect time to:

• Get actual quotes for Marketplace plans

• See how those costs fit into your retirement or pre-retirement budget

• Start building a transition plan that doesn’t leave you uninsured or overspending

Why This Matters Even More in Your 50s and 60s

Healthcare is one of the biggest expenses in retirement. The closer you are to retirement, or to scaling back work, the more your health coverage choices affect:

• Your monthly cash flow

• Your ability to handle a medical surprise

• Your confidence about actually retiring when you want to

The question isn’t just, “What’s the cheapest premium?” It’s:

• What total cost can I realistically handle if the year is medically “normal”?

• What if the year is not normal?

• Am I paying for benefits I don’t use—or underinsuring areas I do rely on?

Choosing well now is one of the most practical ways to protect both your health and your wealth.

A Simple 4-Step Checkup for Your 2026 Coverage

To make this feel more manageable, here’s a quick checklist you can follow:

1. Look back at your 2025 health care.
   List your doctors, specialists, regular prescriptions, and any ongoing treatments.

2. Review your current plan’s 2026 details.
   Log in to your employer portal or the Marketplace and check:

• Premium

• Deductible and out-of-pocket maximum

• Copays/coinsurance

3. Confirm your doctors and drugs.
   Double-check that:

• Your doctors and preferred hospitals are still in-network

• Your medications are still on the plan’s formulary at a cost you can live with

4. Compare at least one alternative.
   Even if you like your current plan, compare it with at least one other option. Sometimes a small shift in network or drug coverage can save you significantly or give you better protection.

If this feels overwhelming, that doesn’t mean you’re “bad with money” or “bad with details.” It means the system is complicated. Getting help, whether from a financial planner, a health insurance specialist, or both, is part of taking good care of yourself.

The Real Point: Future You Deserves Care, Not Chaos

Underneath all the deadlines and jargon, this is about one thing:
Making sure you can get the care you need without blowing up your financial life.

For pre-retirees and retirees especially, health care isn’t a side issue, it’s central to whether you can retire when and how you want.

Taking one focused block of time before the December 15 deadline to review your coverage, your prescriptions, and your out-of-pocket exposure is an act of respect for yourself and the people who love you.

You don’t need to love health insurance. You just need to give it a thoughtful look while you still have the power to choose. Your 2026 self will be very grateful you did. And remember to stay financially fit and fearless, and keep planning your next fabulous step!