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Smart Money

Self-Employed? Here’s Your Open Enrollment Checklist

If you're self-employed, Open Enrollment is the only time of year to buy or change your health insurance without a qualifying life event. Here's what you need to know.

Sydney Frazer • November 15, 2021

In This Article

  1. When is Open Enrollment?
  2. What happens if you miss Open Enrollment?
  3. Your Open Enrollment Checklist
  4. Make sure to compare your options

This is a guest post by one of our partners, Stride Health. This post contains partner affiliate links. For more information on how we work with partners, see disclosures at the bottom of this page. 

If you don’t have access to employer-sponsored health insurance, Open Enrollment Period (OEP) is the only time of year that you can buy or change your health insurance without a qualifying life event. This is a deadline you don’t want to miss, especially if you’re self-employed! You may be eligible for new and/or less expensive plans that can help you save on the cost of care in 2022.

Find your plan (10 mins)

When is Open Enrollment?

For most states, OEP for 2022 health plans starts November 1, 2021 and ends January 15, 2022. This gives you just around 11 weeks to sign up. However, if you want coverage beginning January 1, 2022, you’ll need to enroll by December 15, 2021. If you enroll between December 16, 2021 and January 15, 2022, your coverage will begin February 1, 2022 instead.

Keep in mind: Not all states have these same deadlines as they manage their own health marketplaces. In the case you live in any of the following states, you’ll want to ensure you enroll by the deadlines below: 

  • California: November 1-January 31
  • Massachusetts: November 1-January 23
  • Minnesota: November 1-December 22
  • New Jersey: November 1-January 31
  • New York: November 16-December 31
  • Rhode Island: November 1-January 23
  • Washington, D.C.: November 1-January 31

What happens if you miss Open Enrollment?

If you don’t buy health insurance during OEP, you will not be able to purchase health insurance until OEP the following year (unless you experience a qualifying life event.) Qualifying events include big life changes like having a baby, getting married, or moving to a new state. While these qualifying events vary in nature, most have one thing in common: you need to have had health insurance prior to the qualifying event in order to be eligible to enroll.

Your Open Enrollment Checklist

When it comes to saving money on health insurance, a little work goes a long way. Spending time each Open Enrollment to pick your optimal plan can save you thousands of dollars on care. Here’s what you need to do: 


✅ Brush up on your health insurance terminology 

The nitty-gritty health insurance details make a big difference in how much money you’ll owe for your health care. Get to know these terms so you can be a smarter shopper:

  • Premium: Your monthly plan payment
  • Deductible: The amount of money you have to spend before health insurance kicks in. Higher premiums are typically paired with lower deductibles
  • Co-pay: A flat fee for care, such as $25 doctor visits and or $10 prescriptions
  • Co-insurance: The portion of the medical bill you’re responsible for after you hit your deductible (such as 20%)
  • Out-Of-Pocket-Maximum: The most you’ll pay in a year on covered medical costs 
  • Metal Tier (Bronze, Silver, Gold, Platinum): Your health plan’s level of cost and coverage. More on this later! 
  • Network type: The type of access your health plan offers to doctors, specialists, hospitals, etc. 
  • HMO: Requires you to select a primary care physician (PCP) who will refer you to in-network specialists or diagnostic services. Out-of-network costs aren’t typically covered.
  • PPO: No referrals required. You will be responsible for choosing care from your plan’s preferred network of providers. Out-of-network care will be partially covered. 
  • EPO: No referrals required. You will be responsible for choosing care from your plan’s preferred network of providers. Out-of-network care will not be covered. 
  • POS: Requires you to select a primary care physician who will refer you to specialists or diagnostic services. Out-of-network care will be partially covered. 
  • HSA Eligible: Health plans that can be paired with a tax-free savings account


✅  Review your current health plan details 

If you’re currently enrolled in a health insurance plan, keep an eye out for a notice from your insurer. See a price change? Don’t panic! Thanks to expanded financial assistance provided by the American Rescue Plan Act (ARPA), you could end up paying less for coverage, even if your plan went up in price. The US government estimates that 3 in 5 uninsured Americans can qualify for health insurance completely free of cost, while 4 in 5 people can find a plan for less than $10 per month.

It’s also a good idea to check this notice for any changes to your benefits. Insurers may add, remove, or adjust the coverage on some plan benefits each year, so keep an eye out for the items that are important to you. If you see a change you don’t like (or want to take advantage of any extra financial assistance you receive this year), consider looking for a better plan. 

Note: If you’re currently uninsured, this could be the year you find affordable coverage. Plan prices and subsidy amounts change year-to-year. There may be affordable plan options available to you that you didn’t see last year, so it’s always worth shopping around.


✅  Make a list of your doctors + meds

Have a list of your preferred providers, specialists, and medications ready to go. Doctors constantly change which plans they accept, so you’ll want to call and confirm they’re covered once you find a plan you like. While shopping, you can also confirm prescription information by researching your potential insurer’s prescription drug tiers. 


✅ Evaluate your current + upcoming health care needs

Consider some of these questions before diving into plan shopping:

  • How much health care did you use this past year?
  • Did you pay full-price for several doctor visits and prescriptions this year? 
  • Have you or a family member been recently diagnosed with a medical condition? 
  • Are you or a family member pregnant or trying to conceive?

As your family’s health care needs evolve, you’ll want your health insurance coverage to adapt, too.


✅ Think about metal tiers

Health insurance companies organize their plans by metal tiers (bronze, silver, gold, and platinum) to represent different price points and coverage amounts. Essentially, the more you pay each month, the more medical care your insurer will cover.

If you plan to use a lot of health care in 2022, or if you paid full-price for several doctor visits and prescriptions this past year, plan to shop around in a gold or platinum metal tier; even though you pay more money up-front, your insurer will cover more of your medical bills, which could save you money in the long run.

If you’ve been paying for an expensive plan but rarely use it, or if you simply don’t have many medical costs, consider shopping for bronze and silver plans. These have higher deductibles, so you’ll owe more when you visit the doctor; however, your medical costs could balance out with your less-expensive monthly premiums.

Note: Don’t forget about health savings accounts,HSAs). An HSA is a tax-free savings account specifically for health-related expenses. If you’re shopping for a high deductible plan, keep an eye out for HSA-eligible ones; HSAs are a savvy way to reserve funds in case you encounter large medical bills.


✅ Calculate your income for the year

To buy health insurance for 2022, you need to estimate your 2022 income. That’s because your annual income determines how much you receive in subsidies. A subsidy is the amount of money the government puts towards your plan’s monthly premium. Subsidies are essentially free financial assistance.

If you’re not sure how much you’ll make next year, it’s okay to use this year’s income as an estimate. But try to be as accurate as possible. If you underestimate your income and receive a higher subsidy as a result, you may have to repay some of that financial assistance at tax time.

Self-employed workers get to factor in tax deductions when calculating income. Deductions include business expenses like mileage, home office costs, and cell phone bills, as well as personal expenses like student loan interest and IRA contributions. The more deductions you have, the more you can potentially save on health insurance.

For a guided walk-through on how to accurately calculate your MAGI (Modified Adjusted Gross Income), head here


✅ Plan to shop a few weeks before the deadline

Make time to shop for a plan well in advance of your local OEP deadline. Often, health insurance applications are held up by website delays, verification errors, information requests, and more. Giving yourself extra time to shop ensures you can get help when needed and finish your application before it’s too late.

When shopping for health insurance, you can enter your health info directly into Stride’s free plan comparison tool to see which plans cover your requirements.

Learn More

When shopping for health insurance, you can enter your health info directly into Stride's free plan comparison tool to see which plans cover your requirements.

Make sure to compare your options

Finding health insurance that meets your unique financial and health needs doesn’t have to be a hassle. Stride makes it easy to compare your options, see if you qualify for savings, and more. Plus, their on-call health insurance experts are available to help you understand your health insurance and savings options.


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