Self employed…should I enroll in Medicare Part B?

Published 12:00 am Saturday, June 5, 2021

Hello Toni:

I need your help about enrolling in Part B or delaying it. I am self-employed with no employees, turning 65 with an individual Blue Cross/Blue Shield health 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 that I do not need Part B.

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


Hello Bill:

Great Medicare question, Bill. Last week, I consulted with a person that is also self-employed but was given wrong advice about delaying his Part B. His Medicare nightmare is now starting. Medicare does not recognize individual plans like yours as “true company” benefits with creditable prescription drug coverage for delaying your Part B. Now this fellow who is 66 will receive not only a 10% penalty for each year due to not enrolling in Part B at the right time, but a 20% penalty (two years, 65 and 66) each month for as long as he is on Medicare, or should I say the rest of his life. The 20% penalty goes up as the Part B premium changes. Stinks, doesn’t it?

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 to keep from giving you 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 first day of the month you turn 65, you can sign up for Medicare anytime during the three 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 and losing your or your spouse’s company benefits. The Medicare and You Handbook discusses under the subtitle of “Should I enroll in 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 eight-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 eight-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 your or your spouse’s employer group health plan is ending, to be sure there is medical coverage when a healthcare need occurs.


            The 2021 Confused about Medicare and LTC Zoom webinar is at 4 p.m. Thursday, June 24. Visit to sign up for Toni’s new webinar event. Toni King, Medicare author/advocate, is giving a $5 discount to the Toni Says® readers on the new 2021Medicare Survival Guide® Advanced book at Have a Medicare question? Call 832-519-8664 or email