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Open Enrollment for the self-employed, the plain version

Open Enrollment is the yearly window when you can sign up for, renew or change a Marketplace health plan for the coming year. For 2027 coverage, healthcare.gov says it starts November 1, the last day to enroll for coverage that starts January 1 is December 15, and it ends January 15. Outside that window you generally need a qualifying life change to enroll.

Last updated

Nobody sends the self-employed a benefits email. These are the dates.

The dates, from healthcare.gov

These come from healthcare.gov's dates and deadlines page. We check them again the week this guide is published, and the official page always wins over this one.

  • November 1: Open Enrollment starts. You can enroll in, renew or change a Marketplace plan for the coming year.
  • December 15: the last day to enroll in or change plans for coverage to start January 1.
  • January 15: Open Enrollment ends.
  • If you enroll or change plans between December 16 and January 15, healthcare.gov says coverage starts February 1, once you pay your first premium.

The two letters to read first

If you have Marketplace coverage now, healthcare.gov says you should get two letters by November 1: one from your insurance company and one from the Marketplace. They tell you whether your plan is offered next year and which plan, if any, you are matched with if you do nothing.

Three choices, one at a time

Every household lands on one of three. None of them is right for everyone.

  • Keep what you have

    If you don't act by December 15, healthcare.gov says you may be automatically re-enrolled for January 1 coverage. In some cases you won't be. Before you let it happen, check the plan you are matched with. Our auto-renew guide is a five-point checklist for that.

  • Change plans

    A new client mix, a year of uneven pay, a new baby or a spouse's new job are all reasons to look again.

  • Leave the Marketplace

    Some households move to a spouse's employer plan or to coverage bought outside the Marketplace. Before you drop anything, have the new coverage confirmed in writing, so there is no gap.

Where self-employed people get stuck

Mostly on the income question. The Marketplace application asks you to estimate your net self-employment income for the year you want coverage, not last year's. When work comes in by the job or the invoice, that takes some thought. Our income guide covers what the application asks for 1099 and LLC income.

The second sticking point is a job offer. healthcare.gov says that once you have an offer of job-based coverage, in most cases you no longer qualify for a premium tax credit on a Marketplace plan, whether you take the job plan or not. If you or your spouse has an offer, bring it to the call.

The third is hiring. healthcare.gov says that if your business has even one employee other than yourself, a spouse, a family member or an owner, you may be able to use the SHOP Marketplace for small businesses instead. Hiring contractors alone does not make you an employer.

If you miss it

Missing January 15 does not always mean waiting a year. A Special Enrollment Period lets you enroll outside Open Enrollment after certain life changes, such as getting married, having a baby, moving to a new ZIP code or county, or losing other health coverage. healthcare.gov lists them and sets the time limits, usually 60 days from the change.

If none of those apply, a licensed advisor can tell you what, if anything, is open to you before next year's window.

Who this is not for

If a subsidized Marketplace plan still fits your household, healthcare.gov is usually the simpler route, and you can enroll there directly. This guide is written for self-employed households paying most or all of the premium themselves.

Who we refer you to

Ryan Michalek at Michalek Health Solutions. NPN 21043091, NABIP member #525458. Both are public records, and both are worth looking up before you talk to anyone about coverage, this site included.

He looks at your situation and tells you what you may qualify for, including when the answer is to keep what you have.

Ryan Michalek

Michalek Health Solutions

NPN
21043091
NABIP member
525458

Our licensed partner is five-star reviewed on Google. The rating is the partner’s own.

Both numbers are public records. Worth checking before you talk to anyone about coverage, this site included.

Talk it through with a licensed advisor

Ryan Michalek at Michalek Health Solutions (NPN 21043091) is the licensed advisor OwnBossHealth refers readers to. There is no fee to you for the conversation.

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Open Enrollment: questions

When is Open Enrollment for 2027 coverage?

healthcare.gov says Open Enrollment runs from November 1 to January 15. Enroll by December 15 for coverage that starts January 1. Check healthcare.gov for the current dates, because the official page is the one that counts.

Can I buy Marketplace coverage if I am self-employed?

Yes. healthcare.gov says freelancers, consultants, independent contractors and other self-employed workers without employees can enroll through the individual Marketplace.

What happens if I do nothing?

healthcare.gov says that if you don't act by December 15 you may be automatically re-enrolled for January 1 coverage, and in some cases you won't be. Your letters tell you which applies. Check the matched plan before you let it renew.

I missed Open Enrollment. Can I still get covered?

Possibly. Certain life changes, like marriage, a new baby, a move or losing other coverage, open a Special Enrollment Period, usually for 60 days. healthcare.gov lists them. A licensed advisor can tell you what applies to your household.

Is OwnBossHealth an insurance agency?

No. OwnBossHealth is an independent information and referral resource, not an insurance agency or carrier. We connect you with a licensed insurance advisor, Michalek Health Solutions (NPN 21043091).