Self-Employed and Health Insurance: Why Dec. 15 Is So Important


The period between mid-November and mid-January is arguably the busiest for insurance brokers specializing in employee benefits. It is also pretty busy for general agencies. Why? Because that is when most companies offer open enrollment for benefits plans. But the window is a bit shorter for the self-employed. So short that December 15 is usually the cutoff date.

The self-employed, particularly those who work as independent contractors and sole proprietors, need to pay attention to a number of key dates throughout the year. They must file their quarterly estimated taxes on April 15, June 15, September 15, and January 15. And right between the third and fourth quarterly tax payments is the December 15 deadline for open enrollment.

Open enrollment for the self-employed? Absolutely. Self-employed workers are no different than the rest of the workforce in the sense that they are limited as to when they can sign up for new health insurance or modify their existing coverage. And in most states, the open enrollment deadline is December 15. Miss it and you could find yourself out in the cold.

What Happens If It Comes and Goes

December 15 coming and going without the self-employed paying any attention is not unusual. Independent contractors and gig economy workers are often so focused on making clients happy that they do not think too much about their own situations. As someone who falls under the self-employment category, I know this from firsthand experience.

The end of the year is particularly busy as clients want to get things wrapped up before the Christmas and New Year’s holidays. So November and December can be extremely hectic. It is not unusual for contractors and gig workers to completely forget about their own health insurance.

Brokers Can Help a Lot

It is ultimately up to self-employed people to take care of their own health insurance. The fact that they are self-employed does not absolve them of that responsibility. However, I firmly believe that those of us who work for ourselves could benefit from a bit more interaction with insurance brokers. Brokers could help a lot in the pursuit of health insurance and other benefits.

Dallas-based BenefitMall provides brokerage general agency services to brokers across the country. They encourage brokers to consider working with the self-employed as a way to expand their book of business. How does this help individuals? It is pretty simple: brokers keep track of deadlines. They shop around for the best benefits packages. They do all the work so that the individual only needs to decide on their best options.

The only caveat here is that brokers do not get involved in government-backed insurance programs purchased on federal and state exchanges. If a self-employed individual wants to purchase a subsidized exchange plan, they are most likely going to have to do so without any help.

It is Your Only Shot This Year

At the time this post was written, self-employed people had about a month to make their insurance choices. Depending on when you read this, you could be looking at your only shot to get health insurance this year. Should you miss the December 15 deadline, you are going to have to wait until 2024.

Admittedly, the way the system works is absolutely insane. It doesn’t have to be this way. But it is, so pay attention to the looming deadline if you are self-employed and plan to purchase insurance. Go ahead and ignore December 15 if you do not plan to carry health insurance for 2024. You can continue doing what you do, concentrating more on your customers.



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