When you transitioned to freelance, you were excited by the world of possibilities ahead of you but also unnerved by the looming unpredictability. Taking the big leap into self-employment is a dream come true for many. But it also comes with a slew of new responsibilities and expenses. One of the most critical such expense is health insurance.

As a solopreneur, ensuring your health needs are catered for is vital to have continuous cash flow. That said, health insurance plans are not created equal. Note that your age will be a factor on what plan is best for you so My Coverage Options If I’m Turning 26 Soon is a good read.

Shop around and identify a plan that you won’t regret later. Here’s how to do it.

Study Your Medical History

What frequency and intensity of healthcare do you expect you’ll need over the coming year? It’s impossible to predict with accuracy what problems you may face in the future. Nevertheless, your medical history in the preceding 2-3 years should provide a relatively reasonable estimate of what could happen in short to medium-term.

People will range from those who have low utilization of medical services (visits a doctor no more than twice a year and has none or minor prescription medications) to the ones with high use (at least one hospital stay, seven or more doctor visits, lab tests, and ongoing high-cost prescriptions). Evaluating your medical history will prepare you to pick the right insurance plan.


Through your immediate former employer, you were most probably enrolled in a healthcare insurance plan. You are likely to be deeply conversant with this plan and how it works. You could, for instance, already be familiar with a specific doctor or health center within the plan’s network.

On this basis, you may opt to continue with the same plan as a freelancer (though this could get fairly expensive) or you could sign up for a different and more appropriate plan with the same insurer. Overall, the knowledge makes it easier to shop for plans from other insurers since you know what questions to ask. Also, now there is an option for buying a group health insurance even if you are a self-employed, but you have to check the pros and cons first.

Compare Monthly Premiums

One of the things you discover quickly when looking at insurance plans as a freelancer is how expensive the plans are compared to an identical plan you had when you were employed. When it comes to the cost of a healthcare plan, the monthly premium is the first thing most freelancers will look at. And for good reason since it’s the headline cost that insurers will usually emphasize the most.

Actually, the premium should come last in your list of cost considerations as we will find out when examining the other expenses below. In a nutshell, plans with low premiums often compensate for that with higher additional expenses when compared to plans with higher premiums.

Make sure to take care of your finances while choosing a plan, to make the most out of your healthcare.

Compare Annual Deductibles

The annual deductible is the amount of money you’ll have to pay before the insurance cover begins to cater for some of your health costs. Usually, generic drugs and routine checkups will be covered by the plan without crossing into the deductible territory.

There’s an inverse correlation between deductibles and premiums. Plans with high premiums can have yearly deductibles as low as zero. On the other hand, plans with low premiums will have a deductible in the thousands of dollars.

A high deductible isn’t necessarily a bad thing. If you are relatively healthy and have few medical expenses, a plan with a high deductible may actually be best. It will cover a major unexpected illness or emergency as you pay relatively little in monthly premiums.

Compare Out-of-Pocket Maximum

Pay close attention to the yearly out-of-pocket cost. Envisage the worst-case scenario. If you incurred a ton of medical expenses, what could you afford to pay out of pocket comfortably? The out-of-pocket maximum will vary from plan to plan but once again, examine how each plan’s maximum compares with the premium and deductible.

That being said, the out-of-pocket maximum gets reset every year so even if you settle on a plan with an attractive maximum, make sure the plan is just as attractive after each annual review.

Cost of Drugs

The cost of the medication will depend on whether the drugs are brands or generic. There are also different classes of brand drugs: preferred, non-preferred, and specialty. Generic drugs are considerably cheaper, and people who take them won’t necessarily need to scrutinize this section of the plan too much.

However, if you suffer from a chronic condition that can only be treat by a specific and pricey set of brand drugs, the insurance plan’s prescription drug coverage is something you’ll want to spend time reading and interrogating. That’ll protect you from unpleasant surprises in the future.

Copay and Coinsurance

Low monthly premium plans often have higher copays and vise Versa. The copays will vary from service to service even within the same plan. Even if you do not anticipate frequent doctor visits. It’s good to take a look at how much it’d cost to see an optometrist, OBGYN or other specialty visits. Also, check out the co-pays for trips to urgent care and ER, lab work, and x-rays.

Depending on the plan, you may be requires to pay co-insurance. This is a percentage of the expenses for drugs, primary care visits, and more in addition to the co-pay. That’s irrespective of whether you have met your deductible or not. Again this should be a determining factor in choosing a plan.

Make no mistake; selecting an insurance plan as a freelancer is tough. First, you no longer have an employer to negotiate on your behalf. Second, insurers won’t be as aggressive in courting you as they would an employer bringing in hundreds or thousands of employees.

In fact, the stress of identifying health insurance is one of the first things that could make you entertain the thought of returning to traditional employment. However, with good research, planning, and calculation, you can overcome the anxiety and find a plan with the right combination for you.

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