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The self-employed guide to open enrollment

Navigating the ACA can be complicated. Here’s how to get the best health insurance for you and your family.

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This year marks the twelfth anniversary of the Affordable Care Act — and according to a recent “State of the ACA” report from the Centers for Medicare & Medicaid Services, a record-breaking 14.5 million people received health insurance coverage through the ACA Marketplace in 2022.

If you were one of the millions of people who applied for ACA coverage, you know how important your annual health insurance decisions can be.

Choosing the best Marketplace plan for you and your family is one of the best ways to save money on healthcare costs, but health insurance options are often confusing. What is coinsurance, and how is it different from a copay? What happens when you meet your deductible but still haven’t met your out-of-pocket maximum? Which plans provide access to the doctors and hospitals you are most likely to use?

Luckily, you don’t have to navigate Open Enrollment on your own. Haven Life recently partnered with Stride Health, a service that specializes in providing healthcare to 1099 independent contractors.

Stride Health is an approved partner of, which means that if you need an Affordable Care Act health insurance plan this year, Stride Health can help you sort through your options and choose the best plan for yourself and your family. Stride Health can also help you choose vision and dental plans.

While services like and Stride Health are designed to help people make smart Open Enrollment decisions with as little stress as possible, it’s still a good idea to understand how Open Enrollment works — including when to apply, how to compare coverage options and how to estimate annual medical expenses — before you start choosing health insurance plans.

That’s why we put together this guide. If you’re a freelancer, independent contractor, or a gig worker looking for health insurance in 2023, here’s what you need to know.

In this article:

Apply for health insurance before Open Enrollment ends

If you want Affordable Care Act health insurance coverage in the 2023 calendar year, you’ll need to apply for coverage while Open Enrollment is active. This year, Open Enrollment begins on November 1, 2022 and ends on January 15, 2023.

After Open Enrollment closes, the only way to access an ACA Marketplace plan is by qualifying for Special Enrollment Period, or SEP. If you move, get married, have a baby, adopt a child or lose existing health insurance coverage, you may be able to apply for ACA healthcare coverage under a SEP.

Last year, the U.S. Department of Health and Human Services established an ongoing Special Enrollment Period for households with income levels not exceeding 150% of the Federal Poverty Level. Under this SEP, qualifying households could enroll in an ACA Marketplace plan at any time during the 2022 calendar year.

It’s unclear right now whether this new SEP will continue into 2023 — but it still might be a good idea to complete your application during the annual Open Enrollment period. If you start early, you can get your 2023 health insurance coverage in place before 2022 ends.

Know how to compare coverage options

If you understand how to compare health insurance plans and anticipate annual medical expenses, you’ll be more likely to choose a health insurance package that can meet your family’s expected needs — as well as handle any surprises that may come up. You’ll also be better prepared to use cost-saving tools like health savings accounts to manage your deductibles, copays, prescription costs and more.

Stride Health can help you evaluate your options and choose health insurance coverage — and services like and your state’s Marketplace website may also provide useful comparison tools. Here are some terms to keep in mind as you compare potential insurance plans:

Some health insurance plans charge higher monthly premiums in exchange for lower deductibles. Other plans charge low monthly premiums but require you to pay a large deductible before your insurer will begin sharing costs.

You may also be eligible for a health insurance subsidy, also known as a premium tax credit. These credits are based on annual income, and can help lower the cost of health insurance by reducing the amount you pay in monthly premiums.

If you’re a freelancer or gig worker who has trouble predicting your annual income in the gig economy, don’t worry — if you miss out on your health insurance subsidy when you apply for 2023 health care coverage, you can claim a tax credit equivalent to the subsidy amount on your 2023 taxes.

Don’t forget vision and dental

Affordable Care Act health insurance plans are not required to include vision and dental coverage for adults. The rules are slightly different for people under 18 — as are the responsibilities. All Marketplace plans are required to include vision coverage for children under 18, and although Marketplace plans must offer dental coverage for children under 18, it is not required of you to buy it.

Does that sound complicated? Don’t worry. Services like Stride Health can help you navigate your vision and dental options, and help you create a customized coverage plan — whether you’re an adult who needs vision or dental coverage, or a parent who wants to ensure your kids have access to glasses, braces and annual checkups.

Consider adding life insurance to your coverage plan

There’s one more thing to consider as you explore your Open Enrollment options. If you haven’t yet applied for life insurance, you might want to consider adding a term life insurance policy to your coverage plan.

No, you won’t be able to purchase life insurance through the ACA Marketplace — but you can use services like Haven Life to apply for affordable life insurance coverage that can protect your family during a worst-case scenario.

That way, you’ll have everything you need to start 2023 with the best possible insurance coverage — and you’ll be prepared for nearly anything the year brings.

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About Nicole Dieker

Nicole Dieker has been a full-time freelance writer since 2012, with a focus on personal finance and habit formation. In addition to Haven Life, her work regularly appears at Lifehacker, Bankrate,, and Vox. Dieker spent five years as a writer and editor for The Billfold, a personal finance blog where people had honest conversations about money, and is the author of Frugal and the Beast: And Other Financial Fairy Tales.

Read more by Nicole Dieker

Our editorial policy

Haven Life is a customer-centric life insurance agency that’s backed and wholly owned by Massachusetts Mutual Life Insurance Company (MassMutual). We believe navigating decisions about life insurance, your personal finances and overall wellness can be refreshingly simple.

Our editorial policy

Haven Life is a customer centric life insurance agency that’s backed and wholly owned by Massachusetts Mutual Life Insurance Company (MassMutual). We believe navigating decisions about life insurance, your personal finances and overall wellness can be refreshingly simple.

Our content is created for educational purposes only. Haven Life does not endorse the companies, products, services or strategies discussed here, but we hope they can make your life a little less hard if they are a fit for your situation.

Haven Life is not authorized to give tax, legal or investment advice. This material is not intended to provide, and should not be relied on for tax, legal, or investment advice. Individuals are encouraged to seed advice from their own tax or legal counsel.

Our disclosures

Haven Term is a Term Life Insurance Policy (DTC and ICC17DTC in certain states, including NC) issued by Massachusetts Mutual Life Insurance Company (MassMutual), Springfield, MA 01111-0001 and offered exclusively through Haven Life Insurance Agency, LLC. In NY, Haven Term is DTC-NY 1017. In CA, Haven Term is DTC-CA 042017. Haven Term Simplified is a Simplified Issue Term Life Insurance Policy (ICC19PCM-SI 0819 in certain states, including NC) issued by the C.M. Life Insurance Company, Enfield, CT 06082. Policy and rider form numbers and features may vary by state and may not be available in all states. Our Agency license number in California is OK71922 and in Arkansas 100139527.

MassMutual is rated by A.M. Best Company as A++ (Superior; Top category of 15). The rating is as of Aril 1, 2020 and is subject to change. MassMutual has received different ratings from other rating agencies.

Haven Life Plus (Plus) is the marketing name for the Plus rider, which is included as part of the Haven Term policy and offers access to additional services and benefits at no cost or at a discount. The rider is not available in every state and is subject to change at any time. Neither Haven Life nor MassMutual are responsible for the provision of the benefits and services made accessible under the Plus Rider, which are provided by third party vendors (partners). For more information about Haven Life Plus, please visit:

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