I'm self-employed and turning 65 — how do I transition to Medicare without employer coverage?

Question

Mike Alexander · Accepted Answer

Go to wwa ssa.gov 3 months before you turn 65 and enroll in medicare A & B
Then you can decide on either a supplement plan or an advantage plan depending on your budget

Daniel Brechin · Answer

Yes, you should be able to enroll.  There are two questions: Do you have Medicare Part A and Part B? Do you have an election event to make a change?
At Age 65, you have an enrollment period that will run 3 months before the month of your Birthday.  The month of your Birthday and 3 Months prior you will have an election to enroll in Medicare.

Danny Brechin 

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Edward MacConnell · Answer

If you have met Medicare eligibility requirements you can simply enroll on Medicare part A and B through your local Social Security office or online at Medicare.gov.

Paul Barrett · Answer

Turning 65 while self-employed is actually one of the cleaner Medicare transitions — no employer HR to coordinate with, no group plan to untangle. Here's what matters most:
You have a 7-month window centered around your birthday to enroll. Miss it, and you could face lifetime penalties on your Part B premium — so timing is everything.
If you've been on a marketplace or individual plan, it simply ends when Medicare begins. Just make sure the dates align so you're not caught with a gap — or paying for both at once.
You'll choose between two paths:
Original Medicare paired with a Medigap supplement gives you predictable costs and the freedom to see virtually any doctor. Medicare Advantage typically has lower premiums but comes with network restrictions and variable out-of-pocket costs. One isn't universally better — it depends on your health, your budget, and how you use your coverage.
Don't skip Part D. Even if you're on zero medications today, enrolling in drug coverage when you're first eligible protects you from a penalty that follows you for life.
The good news? You don't have to sort through any of this alone. Working with an independent Medicare agent costs you absolutely nothing — and having someone in your corner who knows this stuff inside and out makes the whole process a lot less stressful.

Tony Spikes · Answer

It is a very simple transition to Medicare if you use a knowledgeable broker that has access to all the major companies.
First step go to ssa.gov to sign up for Medicare part A part B three months in advance of your birth month. 
ie: August birth month = May 1 sign up. 
(unless your birthdate is the 1st day of the month).

William Brobson · Answer

When you reach the age of 65 you automatically qualify for Medicare. As long as you have contributed to Social Security and Medicare for 40 Quarters part A is automatic. If you have not contributed for 40 Quarters you will have to pay a premium for part A. When you turn 65 you have an open enrollment period running from 3 months prior to turning 65 to 3 months after you turn 65 to sign up for Medicare part B. This does not include the month you turn 65. You can sign up for Medicare one of 2 ways. You go to the Social Security Office, or you can sign up on the Social Security web site or the Medicare Web sight.

Answered by William Brobson on April 10, 2026

Agent Licensed in SC, GA & VA

Answered by William Brobson Medicare Insurance Agent

Steven LaPorte · Answer

You have three months prior and three months after your 65th birthday to apply for Medicare part A. You can at the same time apply for Medicare part B and choose a Medicare plan that best fits your circumstance.

Answered by Steven LaPorte on April 13, 2026

Agent Licensed in LA, MS & TX

Answered by Steven LaPorte Medicare Insurance Agent

Maureen Wark · Answer

You would enroll in either a Medicare Supplement with Prescription drug Plan or a Medicare Advantage plan effective the first of the month you turn 65. 
If you are not receiving your Social Security benefits yet, make sure to apply for Medicare Part A and Part B two to three months before the month your turn 65. 
Those dates and the effective date of your Medicare plan(s) should match. 
If you have a Marketplace plan now, make sure to cancel it the date your Medicare is effective and your plan(s) in place

Brooke Smith · Answer

You need to enroll during your Intitial Enrollment Period (during the 3 months before your 65th birthday, the month of your birthday, or 3 months after). You have a 7 month enrollment window to apply without a penalty. Once you sign up for Medicare, you can then decide which plan you want to go with:

* A Medigap (also referred to as a Medicare Supplement Plan)
- These plans help fill in the gaps left by Original Medicare ensuring you aren't left vulernable to high out of pocket costs. These are paired with a stand alone Prescription Drug Plan. 

*  Medicare Advantage Plan)
- These are copay based plans offered through private insurance companies. These typically will include drug coverage and other perks such as dental, hearing, and vision.

Even without an employer, your time frames are the same. You will enroll in Medicare during your 7 month window.

Michelle Walls · Answer

Hello,

Your Medicare coverage will become effective on the first day of the month in which you turn 65. You should receive information from Social Security before that time. Be sure to let them know that you would like to enroll in both Medicare Part A (hospital coverage) and Part B (doctor visits and medical supplies).

Once you receive your Medicare ID card showing the effective date, you can notify your current insurance provider that you are transitioning to Medicare and request cancellation of your coverage effective the last day of the month prior to your birthday month.

I hope this information is helpful, 

Michelle

I'm self-employed and turning 65 — how do I transition to Medicare without employer coverage?

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I'm self-employed and turning 65 — how do I transition to Medicare without employer coverage?

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