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⚕️Insider Tips: Making the Most of Your Health Insurance, as an Entrepreneur or Freelancer

Updated: Feb 3, 2023

Navigating health insurance can be overwhelming, even as a property claims professional. Justis Wilson of Live Well Health Consulting, provides tips and best practices to consider.

an umbrella floating above a lake.
Demistifying the medical coverage conundrum.
Disclaimer: this article does not constitute legal or insuring advice, and is for general information purposes only. Nothing in the Website is intended to be a substitute for formal legal advice and should not be relied upon as such. Read our full site Disclaimer here.

As a freelancer or small business, it can be difficult to stay afloat in today's economy and compete with larger companies, making health insurance an added expense that can feel overwhelming and something that often falls on the back burner.

A photo of a smiling man
The article's author, Justis Wilson

However, health insurance is an important factor to consider when compiling your budget that ensures the hard work you’ve spent building your business isn’t ruined by a surprise trip to the hospital.

The good news is, there are various options available to suit freelancers and small businesses depending on your particular needs.

In this blog post, you'll learn about the various health insurance options available for freelancers and small businesses, including how to choose the right plan. You'll also get insider tips on making the most of your health benefits and tips for saving on health insurance premiums.

Read on to learn more about health insurance for freelancers and small companies.

Do I really need it?

With rising premium and out of pocket prices, it’s easy to just throw up your hands and say “what’s the point?”

Trust me, I get it.

I certainly understand that spending the $150 cash once a year for your annual physical seems more appealing than paying premiums every month, but health insurance is possibly one of the most important financial protections you could have for your business.

While it’s nice to get some benefits like cheaper doctor visits or free lab work with your plans, the real value of health insurance is the peace of mind: that the possibly bankrupting incidences that are bound to happen in your life, will be financially insignificant (or at least manageable).

Furthermore, health insurance can provide access to preventative and primary care services, which can help freelancers and small companies maintain good health and reduce long-term medical costs.

The real and the... Not so real

Now that we’ve established that you do, in fact, need to consider health insurance, let’s learn how to sift out the plans that will actually fit your, and your company's needs.

Luckily, this is much simpler than it looks! Essentially, you need to ask three questions to ensure you’ve got the right stuff:

  1. Do I have a solid "max out of pocket"? This essentially just means that no matter what happens or how expensive those medical bills get, you will never pay more than “x” in a single year.

  2. Do I have an unlimited "max benefit"? This ensures that you will never be capped on your benefits and guarantees that the insurance company will never throw in the towel because your bills started getting expensive.

  3. Lastly, do I have "upfront underwriting" (if any at all)? This one basically just means, if you get approved for a plan they will NOT go searching for a reason not to pay a claim. If you ever hear the terms “point of claim underwriting,” or "post-claim underwriting," turn and run. This essentially means they will let you into the plan, but will have the right and the opportunity to look for any reason they can to tie your claim to pre-existing conditions to get out of paying.

POLL: as a property claims professional, have you struggled with understanding healthcare coverage?

  • 0%Yes! Healthcare coverage is confusing.

  • 0%No, I know a lot about healthcare coverage.

So what do I consider going with?

Well this one is a bit more complicated. If having “real” insurance is important to you, you essentially have three places you can find health insurance, each having their own strengths and weaknesses.


First of your three options would be through an employer sponsored plan. I understand most people reading this are self-employed and don’t have such luxuries, but if you do, consider yourself lucky! These are plans that will most likely cover any pre-existing condition you have and are heavily regulated so you know they are at least dependable.

The only real downsides to this option are that the premiums tend to get a bit pricey when adding a family and the limited options offered may not be custom tailored to your needs.


The next option is something most people are familiar with: the marketplace. You may have heard this called “ACA insurance” or “Obamacare” but it’s all the same thing. Marketplace plans are great options if you are dealing with pre-existing conditions, simply because there are absolutely no pre-existing limitations.

These are also especially useful if you are on the lower end of the income spectrum due to their income based subsidy programs. However, if you ARE doing well financially, these are some of

the more expensive plans out there.

The biggest flaw in marketplace plans is typically their limited networks; with only HMOs and EPOs, your availability of care is limited and you will not have much in the way of coverage when you leave your home county.


The last “real" option out there is underwritten coverage. I like to equate these to a country club; they’re very hard to get into but have some great benefits for those that are able to. These plans are designed to keep healthy people in and the not so healthy people out. For those that can get in, they get to enjoy lower premiums, lower out of pockets, and (most importantly) access to the best nationwide PPO (Preferred Provider Organization) networks available.

Now I don’t want to make these seem like they’re all sunshine and rainbows because they DO have two major downsides. They will not cover anything maternity related or mental health related, but if that’s not a concern of yours, these are great options to save some money and get into great nationwide coverage.

A group of people smiling
Justis Wilson, and the Live Well Health Consulting Team

Final Thoughts

If you take nothing else from this, know these two things:

  1. No matter what your situation is, there is a plan that will work for you.

  2. Finding a knowledgeable, trustworthy agent is very helpful in selecting the right plan for you and your family.

If you need anything at all, my team of specialists and I are more than happy to help in any way possible! We can be reached at (325) 439-0651 or by email at



About the Author: Coming from a small town in West Texas, Justis has always been taught that the first rule of business is to make the client his first priority.

Justis and his team of healthcare agents take the time to have a real conversation with each client, in order to find them the best options available to fit their needs and budget.

Servicing the following states (as of 1/25/23): Texas, Oklahoma, Mississippi, Florida, Georgia, Kansas, Missouri, Alabama, North Carolina, South Carolina, Kentucky, Tennessee, Illinois, Indiana, Ohio, and Colorado.

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