Self-Employed? Here’s Your Open Enrollment Checklist

By Sydney Frazer
October 15, 2020

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 (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 2021.

Find your plan (10 mins)

  1. When is Open Enrollment?
  2. What happens if you miss Open Enrollment?
  3. Your Open Enrollment Checklist
  4. Final word

When is Open Enrollment?

For most states, OEP starts November 1 and ends December 15, giving you just 6 weeks to sign up. Some states choose to extend the window people have to buy health insurance, including: 

  • California: November 1-January 31
  • Massachusetts: November 1-January 23
  • Minnesota: November 1-December 22
  • New York: November 1-January 31
  • Pennsylvania: November 1-January 15
  • Washington: November 1-January 15

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 doctor visits and prescriptions
  • Co-insurance: The portion of the medical bill you’re responsible for after you hit your deductible
  • Out-Of-Pocket-Maximum: The most you can 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. Networks include: 
  • HMO: Requires you to select a primary care physician (PCP) who will refer you to specialists or diagnostic services. 
  • 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 

On average, monthly premiums (your monthly health insurance payments) are increasing slightly due to the pandemic.  If you are currently enrolled in a health insurance plan, keep an eye out for a notice from your insurer. See a price change? Don’t panic!  You can often switch to a cheaper plan in the same metal tier and pay the same (or less) for a similar option.

If you’re currently uninsured, you’re not off the hook! 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 (more info on how to do this here). 

✅ 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 / trying to conceive?

As your family’s health care needs evolve, you 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 2021, 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, saving 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 tend to 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 2021, you need to estimate your 2021 income. That’s because your annual income determines how much you receive in subsidies, money the government puts towards your plan’s monthly premium. Subsidies are essentially free financial assistance.

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.

Final word

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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Sydney Frazer is a Marketing Operations Manager at Stride Health where they help people who work for themselves get the right health insurance at the lowest possible price.

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