If you were born in 1961, this is the year Medicare moves from “someday” to your actual to-do list. It’s one of the most common topics clients in their early 60s ask me about, and for good reason. The choices you make in your first enrollment window can affect what you pay for healthcare for the rest of your life. Here’s what you need to know.
Know your enrollment window
Your Initial Enrollment Period is seven months long: the three months before your birthday month, the month you turn 65, and the three months after. If you sign up in the first three months, your coverage starts on the first day of your birthday month. Sign up later in the window, and coverage begins the first of the month after you enroll.
Already collecting Social Security? You’ll be enrolled in Parts A and B automatically. If not, you can apply online through Social Security. For a look at other ages that matter, see our post on birthday milestones to add to your financial calendar.
Understand the parts
Here’s how the pieces break down for 2026 (our earlier post covers everything you need to know about Medicare in more depth):
- Part A (hospital): Premium-free for most people with 40 quarters of work history. The inpatient deductible is $1,736 per benefit period.
- Part B (medical): Covers doctor visits, outpatient care, and preventive services. The standard premium is $202.90 per month, with a $283 annual deductible and generally 20% coinsurance after that.
- Part D (prescriptions): Offered through private plans. Out-of-pocket costs for covered drugs are capped at $2,100 this year.
- Part C (Medicare Advantage): Private plans that bundle Parts A and B, and usually D, into one package.
- Medigap: Supplemental policies that help cover the gaps in Original Medicare, like that 20% coinsurance.
The big decision: Original Medicare or Medicare Advantage
Medicare Advantage plans often come with lower premiums and an annual out-of-pocket maximum, but they typically use provider networks. Original Medicare paired with a Medigap policy usually costs more each month, but it lets you see any provider nationwide that accepts Medicare and makes your costs more predictable.
If you’ll split time between Washington and somewhere sunnier, read our guide on medical coverage for the snowbird lifestyle.
Your Medigap Open Enrollment Period lasts six months, starting when you’re 65 and enrolled in Part B. During that window, insurers generally can’t deny you or charge more because of your health. Wait too long, and you may face medical underwriting.
Working past 65?
If you have coverage through your own or your spouse’s current employer (generally a company with 20 or more employees), you can usually delay Part B without penalty. You’ll then have an eight-month Special Enrollment Period once that employment or coverage ends.
Two watch-outs. COBRA and retiree health coverage don’t count as current employer coverage for this purpose. And if you’re contributing to a Health Savings Account, those contributions must stop once Medicare begins. Because Part A coverage can be backdated up to 6 months when you enroll after age 65, plan to stop HSA contributions in advance.
Avoid lifelong penalties
The Part B late enrollment penalty adds 10% to your premium for each full 12-month period you could have enrolled but didn’t, and it generally lasts as long as you have Part B. Part D carries its own ongoing penalty if you go without creditable drug coverage.
Don’t overlook IRMAA
Higher earners pay more for Parts B and D through the Income-Related Monthly Adjustment Amount (IRMAA). Your 2026 premiums are based on your 2024 income, with surcharges starting above $109,000 for single filers and $218,000 for joint filers. If your income drops because you retired, you can ask Social Security to reconsider using Form SSA-44. We cover this in more detail in [financial mistakes to avoid in your final working years]([FINAL WORKING YEARS BLOG URL]).
Getting help
Washington residents can get free, unbiased Medicare counseling through SHIBA (Statewide Health Insurance Benefits Advisors), a program of the Office of the Insurance Commissioner. Once enrolled, you can revisit your choices each year during Open Enrollment, October 15 through December 7.
At TFS Advisors, we work alongside trusted Medicare specialists and help you fit healthcare costs into the bigger picture, including your retirement income, tax strategy, and IRMAA planning. Learn more about how we help clients embrace retirement, or schedule a call with our team to talk through your Medicare decisions.
