• Ashley Poynter

Freelancer's guide to health insurance open enrollment



Are you self-employed? Starting a business? Freelancing? If you work for yourself, you’re likely wondering how health insurance open enrollment works. We’re inching closer to this mystical window of time, and for many, it’s a stressful time. There are a myriad of health plans to choose from and it can get hazy determining when you can enroll and what types of plans you can enroll in.


We’re here to help.


If you’re self-employed and looking for a health insurance plan for 2020, you will be able to find options on the health insurance exchange during open enrollment. So what exactly is open enrollment?


A peek inside the open enrollment window

In short, open enrollment is a small period of time every year when you have the opportunity to enroll in health insurance. This is the only time each year that you can sign up for health insurance through the exchange, unless you have a qualifying life event. There are four categories of qualifying life events:


  • Loss of health coverage—you may lose existing coverage, whether it’s job-based, individual, a student plan, or loss of eligibility for another plan.

  • Changes in household—you get married or divorced, have a child, or experience a death in the family.

  • Changes in residence—you move to a different location or to a different type of housing.

  • Other qualifying events—you experience a change to income, leave incarceration, become a citizen, or have some other major change that may qualify.

Outside of those categories, open enrollment usually runs between November 1 and December 15, with plans becoming effective on January 1 of the following year. Those looking for Medicare options should note that open enrollment usually runs from October 15 to December 7 each year.


Why an open enrollment “window” gets dicey for the self-employed



Here’s the thing: life rarely happens within a clean-cut window. People can become self-employed due to a number of circumstances:


  • They are let go from a job and decide to start their own business

  • They quit their full-time job to pursue self-employment

  • They start a side business while working a full-time job and eventually leave the job to pursue business full-time


In some of the cases above, people have the option to continue health care coverage through COBRA (short for Consolidated Omnibus Budget Reconciliation Act). This offers a stopgap for people who undergo a change in life circumstances, rather than immediately losing group health insurance benefits. Unfortunately, COBRA is often expensive and can create a financial burden as premiums must be paid out of pocket.

Some of the circumstances above also qualify as one of the “life events” noted earlier, but that gets complicated, too. When life happens, health insurance is rarely at the top of one’s priority list. Getting fired, experiencing divorce, or moving usually triggers a stress response in people that can impede the ability to find a health plan that is both affordable and comprehensive.


Another thing to remember is that special enrollment periods are not available to people who lost health insurance due to premium nonpayment or if a plan was voluntarily canceled. In those cases, you are out of luck unless you opt for a short-term health plan, which can often be more expensive.


Decent: replacing the window with a door to affordable health insurance


We understand that the struggle is real. Historically, health insurance has not been kind to the self-employed. Between super short enrollment windows or no coverage at all, it’s no surprise that freelancers and small business owners get heart palpitations at the very mention of health insurance or open enrollment. Not to mention, 45 days is not a particularly long time to seek out and vet the plethora of available health plans to find the best fit for your unique needs.


That’s why our timeframe for enrollment is all year long. We offer open enrollment in any of our affordable health plans 365 days a year, so you don’t have to panic come November—or if something comes up before then. Choosing a health insurance plan is a big deal, and we want people to have the time they need to research and understand health coverage options. Make a list and check it twice. Heck, check it a third time. You have all year to enroll in one of our plans. We’re here to serve you, in your time and on your schedule.


Finding an affordable coverage outside the health insurance open enrollment window shouldn’t be a struggle. We’ve simplified it down to two plans with exceptional coverage—built around your needs. What’s more, we offer year-round enrollment, so you can switch to one of our plans at any time. Looking for a change? Get a free quote today.

Team      Press Kit     Providers     FAQ

  • White Facebook Icon
  • White Twitter Icon
  • White LinkedIn Icon

Call us at: (512) 643-4173

We are open 9am - 5pm CST, Monday - Friday

1145 W 5th Street, Austin TX 78703

©2020 Decent.com