Senior Resources » If I’m Self-Employed, Should I Enroll in Medicare Part B?

If I’m Self-Employed, Should I Enroll in Medicare Part B?

man unsure about medicare part b

Dear Toni,


I need your help with enrolling in Part B or delaying it. I am self-employed, with an individual under 65 health insurance plan that covers me and my wife. I have been told by friends that since I am still working, paying taxes, and have health insurance I do not need Part B when I turn 65.

A business associate, who is also self-employed delayed his Part B because he is under his wife’s employer’s group health insurance. I do not want to make a big mistake. Please explain the difference between my situation and my friend’s.



Bill from Tulsa, OK

Great Medicare question, Bill!

Last week I consulted with a person that is also self-employed but was given the wrong information about delaying his Part B. His Medicare nightmare is now starting … Medicare does not recognize individual plans like yours, Bill, as “true company” benefits with creditable prescription drug coverage to delay Part B. 


Now this person who is 66 will receive not only a 10% penalty for each year due to not enrolling in Part B, but a 20% penalty (2 years 65 and 66) each month for as long as he is on Medicare or the rest of his life. The 20% penalty goes up as the Part B premium changes. 

Bill, since you currently have an individual health insurance plan not “true group” health insurance, I would recommend that you enroll in Part B during your “Initial Enrollment Period.”  Many believe that Medicare is automatic, this is only true if you are receiving your Social Security check when you turn 65.

Not working full-time with true company benefits is what Medicare looks for in administering the 10% per year or 12-month period Part B penalty.

If you are not receiving your Social Security check and want your Medicare to begin the 1st day of the month you turn 65, you can sign up for Medicare anytime during the 3 months before your 65th birthday. Go online to to apply for Medicare Parts A and B.

Your business associate who is covered under his working spouse’s “true employer” group health benefits can delay enrolling in Medicare. He must follow Medicare’s enrollment rules as Social Security deems.


“Still working” are magic words when it comes to enrolling past 65 due to losing your or your spouse’s company benefits. The Medicare and You Handbook discusses under the subtitle “I have other health coverage. Should I get Part B?” about delaying Medicare Part B when you are leaving your or your spouse’s group benefits and “that you can sign up for Part B anytime during the 8-month period that begins the month after the employment ends or the coverage ends, whichever happens first”. 

Even though the Medicare & You handbook states that there is an 8-month period that one can enroll without receiving a Medicare Part B penalty, the handbook does not clarify that those who delay will not have any of the benefits that Medicare Part B covers.

During a Toni Says Medicare consultation, we recommend that your and/or your spouse’s Medicare Parts A and B begin the first day that the employer group health plan is ending, to be sure there is medical coverage when a medical need occurs.

Remember, with Medicare… what you don’t know WILL hurt you! Need Medicare help? Call the Toni Says Medicare hotline at (832) 519-8664 or email for assistance. 

Toni’s new book Maze of Medicare is available to purchase at Maze of Medicare is the first book explaining Medicare that includes scripture and positive quotes to help relieve the common stress and anxiety associated with transitioning to Medicare. 

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Originally published July 17, 2023


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