Shopping for health insurance as a freelancer: How I did it


Jackie LamBlog author Jackie LamJackie Lam is a money writer and educator. She helps artists and freelancers get creative with their money at Hey Freelancer.

Published|8 min read

Policygenius content follows strict guidelines for editorial accuracy and integrity. Learn about our editorial standards and how we make money.

Updated Sept. 4, 2019: When I became a full-time freelancer a few years ago, I felt excited but nervous. Taking the leap from a desk job with benefits to solopreneurship was thrilling, but it also came with responsibilities and costs. One expense that needed to be addressed pronto was paying for my own health insurance.

While not exactly on my "awesome stuff to do list," I knew that being hasty about picking a plan would lead to a poor choice. I made sure to spend plenty of time shopping around to see what options were out there.

Here’s how I decided which health care plan to purchase:

Open enrollment

While open enrollment wasn’t until November, because I lost my health coverage after leaving my job in August I qualified for special enrollment and was able to shop for a plan early. I had 60 days to sign up for health insurance, or I would have to wait until November. While I had whole months to enroll, I didn’t feel comfortable going without health insurance for too long.

Health insurance tiers

As I live in Los Angeles, I poked around for rates on Covered California, the state exchange. Plans come in four "metal" tiers: bronze, silver, gold and platinum. Bronze plans have the lowest monthly premium but higher deductibles and out-of-pocket maximums, while platinum plans have the highest monthly premium but lower deductibles.

Policygenius can help you compare health insurance quotes.

Past medical history

When I first hopped onto the Covered California site, I was asked what type of medical service I expected to use for the next year, which ranged from low use (one to two doctor visits a year, few prescription medications), to very high use ( a hospital stay, more than six doctor visits with lab tests, very expensive, ongoing medical prescriptions).

I thought about when I went to the doctor and why. I’d say I fell toward the center of the spectrum. I’m not someone who swears off seeing a doctor unless I’m on my deathbed, but I’m not a full-blown hypochondriac, either.

I mainly went the doctor for routine checkups, and the occasional infection. I didn’t have any chronic medical conditions, just high cholesterol and blood sugar, which required me to go in for lab work a few times a year. I ended up clicking "medium use," which was about three to five visits a year.


Through my former employers I had been enrolled in both HMO plans, which offer coverage only within a specific network, and PPO plans, which also offer some coverage outside of their network (albeit at a higher cost than within the network). Even when I was on the PPO plan, for the most part I would visit the PPO plan’s health centers — low-cost clinics that were great for routine checkups, wellness program and urgent care. This isn’t available on all PPO plans, but mine included this benefit. I’d only tap into the wider PPO network when I needed to see a specialist, such as the time I suffered a minor head injury and went to see a neurologist.

I had also been enrolled in a Kaiser Permanente HMO. While there are limitations with an HMO, such as having to get your prescription drugs at one of their pharmacies, and needing a referral before you can see a specialist, I also was a fan of how you could get everything done through their network. As I didn’t have a doctor outside of Kaiser that I had a longtime relationship with, I would have to spend some time finding a primary care physician.

Being part of the Kaiser network was important to me. In fact, I didn’t even bother looking at other plans. I knew how the system worked, and that some of my medical records were housed there. And because I was familiar with Kaiser, I felt more at ease when shopping around.


I narrowed it down first by the three major types of plans: HMO, a PPO and a faith-based health ministry. When shopping for health insurance and figuring how which tier to purchase, it’s a game of balancing the minimum amount of coverage you need and the maximum out-of-pocket expenses you’re comfortable with—and can reasonably afford.

Monthly premium

All of the plans seemed super expensive, especially since I was used to paying very little for health care through my old jobs. I reminded myself that the monthly payment for bronze plans was the lowest, while the payments for the platinum ones were the highest. While a monthly premium was the one thing I knew I had to pay for, I actually looked at my premium last. I wanted to choose a plan based on other costs to figure out if the premium would be worth it. I focused on the following costs:

Yearly deductible

The yearly deductible is how much you need to pay before insurance starts paying for some of your health expenses. (Usually routine checkups and generic drugs are covered without paying a deductible.) A bronze plan’s deductible was $4,800 for an HMO versus $6,300 for a PPO. If you’re going for a Platinum plan, the yearly deductible can be zero, but the monthly premiums are often twice as much than a bronze plan.

Out-of-pocket maximum

The annual out-of-pocket maximum was something I paid closer attention to. I was thinking about the worst-case scenario: If I racked up a bunch of medical expenses, what could I comfortably afford to pay for out of pocket each year? For instance, a bronze plan could have a maximum up to $6,300 with a separate $500 drug deductible, while a platinum plan could have an annual out-of-pocket maximum of $4,000 with no drug deductible. Even if you stick with the same plan and insurance, the amount gets reset each year.

Cost of drugs

The cost of drugs depends on whether they’re generic or name-brand. When it comes to branded drugs there’s preferred brand, non-preferred brand and specialty drugs. Besides checking the cost of the generic drugs, which I usually get, I kind of glossed over this section. I haven’t had to take pricey prescription medications (knock on wood) so this section didn’t pertain to me. Of course, if you have a chronic medical condition that requires specific, expensive drugs, you’ll want to spend more time scrutinizing this.


I didn’t expect to go to the doctor too frequently, but I also wanted to see how much it would cost to go see an ob-gyn or optometrist, as those were considered specialty visits. I also looked at co-pays for trips to the emergency room and urgent care, X-rays and lab work.


Depending on your plan, you may have to pay a percentage of the costs for primary care visits, drugs and so forth in addition to your co-pay, even after you meet your deductible. I really didn’t want to pay out of pocket for things I most likely would need, like trips to the doctor and some prescription drugs.

There are a ton of costs you can compare and you can spend tons of time agonizing over the details. To make my decision I looked most carefully at the things I would most likely need to pay for based on my past medical history and anything I could anticipate going to the doctor for in the new year.

If you have a particular condition or want more info on something that isn’t easily located online, you can get more info by reaching out directly to the insurance company.

Health ministries

Another option I looked into was faith-based health ministries. It fell onto my radar because a lot of my freelancer pals were raving about it. While it’s not technically health insurance, it is a pool of funds that you contribute to and then tap to pay for your medical bills. And there is something like a deductible which is called a "personal responsibility," and maximum eligibility amounts for certain types of expenses. Depending on the ministry, you either pay your bills and get reimbursed, or have the ministry handle the billing on your behalf.

There were a lot of attractive things about these health ministries: The premiums are set based on the number of people on the plan, and you can opt into a tier that covers $125,000 or $1 million per incident. The rate is the same no matter where you live and how old you are. This is a popular option for full-time RVers, as it’s not limited to state-specific coverage. You can submit a bill from any provider in all 50 states, and sometimes overseas.

However, there are some caveats: You need to live a health-conscious life, including no alcohol or smoking. And when I took a deeper look at the things not covered, such as mental health, eye exams, birth control and accidents and injuries associated with "risky behaviors," such as cancer that could be related to smoking, or car accidents possibly due to reckless driving, I realized that it was not a good fit for me. Although I was no party girl or Evel Knievel, I didn’t want to have to deal with being denied coverage based on some questionable activity.

Besides an annual checkup and a few lab tests a year, I didn’t anticipate going to the doctor too frequently. However, I did want to have visits to the doctor and generic drugs covered with a co-pay, and not have to hit the deductible before my health coverage would kick in. I ultimately decided on a silver-level HMO plan, which had a monthly premium of $290.

I haven’t had many complaints with my plan and have stuck with the same one for the past few years. However, I’m not immune to the general anxiety and fear of millions of fellow Americans who get insurance through the Affordable Care Act. And depending what goes down with Trumpcare, I’ll definitely be spending more time exploring different options.

Want more money explainers in your inbox? Sign up for the Easy Money newsletter.

Ready to shop for life insurance?


No corrections since publication.


Blog author Jackie Lam

Jackie Lam is a money writer and educator. She helps artists and freelancers get creative with their money at Hey Freelancer.

Questions about this page? Email us at .