Everything You Need to Know About Freelancing and Health Insurance


Health insurance.

One of the largest difficulties freelancers face.

Can I afford health insurance for myself? Which provider should I get? Do I qualify for Freelancer’s Union insurance? How high or low should my deductible be?  Should I get a HSA plan? Do I have to get health insurance before Obamacare goes into effect?

It’s a mental maze that can keep you up at night.

When I went freelance almost two years ago, I PROMISED myself I would get health insurance no matter what. And I did. A broker found me a Blue Cross and Blue Shield HSA (Health Savings Account) plan for $110/month with a high deductible and no co-pays. I knew it was essentially “catastrophic insurance”, but I was happy to at least have something. After a short period of time my plan went up for no reason and the financial burden of paying for basic doctor visits became too much. When a pain in my right side popped up last winter, simple blood tests ended up costing me over $500. I was sad and frustrated, and, knock on wood, I have extremely minor issues to deal with as compared to others. I often think about my parents- one who works at Staples at 62 years of age simply so she can have health insurance and another who at 60 can’t find any plan cheaper than $300 a month (again, “catastrophic”; good insurance would cost him between $500-$600). That’s nothing compared to the people who routinely get bad care, kicked out of hospitals or don’t seek important medical treatment solely because of their inadequate insurance or lack thereof. It makes me sick to my stomach when I hear these stories over and over again. So many people die because of our terrible healthcare system.

As a person who tries to inform herself with social issues and politics, I will tell you that Obamacare has been extremely confusing to understand (I also live in a state, Texas, that makes it extra confusing). Though we can read the Obamacare facts over and over, do we truly know how this is going to affect us all in the long run? Maybe I’m being a pessimist, but as a Obama supporter, he has been disappointing me a lot lately.

*Update: I found an AWESOME article on GOOD by Sunaina Sondhi that is a comprehensive and easy-to-understand breakdown of Obamacare. I highly recommend taking a look!

Last week I finally had enough with my Blue Cross and Blue Shield plan that was going up and not covering anything. I checked out the Freelancer’s Union website to see if I could get insurance through there, but discovered that they don’t cover Austin. Instead they recommend inexpensive plans through UnitedHealthOne. I sent a message out on social media asking what people thought of UnitedHealthOne and I got mixed reviews. Some people enjoy it, while my friend and fellow blogger Tolly Moseley said her UnitedHealthOne premiums went up over $100 in a short period of time. Because of this she switched to Humana. I did a quick Google search of reviews on Blue Cross and Blue Shield, UnitedHealthOne, and Humana and I can tell you that the latter two frequently came up as quality providers in the state of Texas, while Blue Cross and Blue Shield received many complaints (this confirmed my want to leave Blue Cross and Blue Shield). Without even thinking, I called Humana and was delighted to talk to a friendly person on the phone. I told her my situation and she unhurriedly broke down what plans they had to offer. Their most popular plan, the one I ended up getting, offer co-pays on doctor and specialist visits, a 70/30 break after the deductible is met with a $7,500 out-of-pocket max, co-pay on prescriptions and a $2,5000 deductible. This plan costs the same as my Blue Cross and Blue Shield coverage ($130/month) which covered NONE of these features until my high deductible was met. I also added a dental plan for only $30 more (dental plans are typically a waste of money, but since I have some major work to be done, the couple extra hundred bucks I might save will be worth it). If you want an even higher deductible with Humana, you can get the same plan in the low $100s or under $100.

I have yet to use my new insurance, but I already know I have a much better provider than before that many of my regular doctors take. Also, I always trust what Tolly says.

Moral of the story: Humana is a great and affordable option for freelancers in Texas. As mentioned above UnitedHealthOne has good reviews as well, but I would recommend staying away from Blue Cross and Blue Shield. I had good experiences with that provider in other states, but not in Texas. As for HSA plans, I was talked into one by the broker. In theory, they are a good way to go: you set aside money that is untaxed to put towards medical bills. However, if you’re a freelancer and don’t make much, this isn’t going to help. I never put money aside and neither the broker or the Blue Cross and Blue Shield website made it easy for me to figure out how to.

If you want to learn more about the best insurance providers in Texas, check out US News health insurance page. Aetna appears to be another strongly rated provider in Texas.

If you are a freelancer and covered by another provider, please share your experiences in the comments! I would love to get a dialogue going about this.

I asked a couple of freelancer friends their experiences with health insurance. This is what they had to say:

Tolly Mosely from Austin Eavesdropper: Ross and I got insurance through United Health/GoldenRule back in the summer of 2010. At the time, we were both working jobs with no health benefits, and he was about to travel to South America so I signed us up. It was pretty much like having no insurance because we had to pay out-of-pocket on all our doctor’s and dental visits, but hey! If Ross caught that disease where a tiny poisonous fish swims up your pee stream and infects your manhood, then at least we’d only have to pay five thousand on his surgeries. 

 Over the years we kept it, because we wanted to be responsible adults but didn’t know our options. Then, I think around 2011, we started getting letters in the mail informing us that our rates were going to be raised. We went from paying $250 to almost $400/mo in less than a year and a half. I got on United’s website to see if there were other plan options we could do, but even finding a phone number to talk to somebody over there was nearly impossible. (Their site has since gotten slightly easier to navigate.)
So we were cursing our new $400/monthly and all frustrated about it, when I was working at the coffee shop one day and ran into another self-employed friend of mine. I’m not sure how we got on the topic, but this saint of a man told me about Humana and how he had their lowest monthly/highest deductible plan for something crazy – like, $80/mo. I got on their website, which was a DREAM to navigate, and clearly laid out aaalllll of my plan options for me and exactly what they covered. We selected a high deductible ($7.5k), low monthly plan for both of us, and added dental. We now pay $224/mo total, our dental cleanings are covered, and I get a free Well Woman (ob-gyn checkup) visit every year.
Come Obamacare, I might log into their marketplace and assess my healthcare options again, because Ross and I want to have a baby and a plan that covers maternity. But, for the time being, we couldn’t be happier with our plan. As two self-employed people, finding good, affordable healthcare is a whole different ballgame than traditional employment! But, it’s not impossible. I think we’re going to see the healthcare process become even better as more and more people go the self-employed route.

Kristin Sheppard from Mad Betty: Freelance has the best perks in the world: ultimate schedule, working in your pajamas, hand picking your clients. There’s no counting meager vacation days and lamenting a long stretch of time without a day off. It’s a dream. Unless you get sick.

The options for individual health insurance range from sucks-a-little to sucks-a-lot. The cheapest of plans will let you down if you actually do need medical care. If you take regular prescriptions, you’ll want a better plan which will cost more. Have even a minor preexisting condition? Prepare to pay through the nose. 
Sadly, I’ve known so many people in this tough situation. Should you pursue your personal and professional goals when they require you to work for yourself and struggle financially to pay an insurance carrier? Or do you just go work for a large company where you might not be getting any career satisfaction, but at least you have a decent plan that’s not breaking the bank? Seems unfair to have to choose between security and dreams, but that’s the position many of us are in.
Health care reform may be messy and controversial, but for a freelancer, it’s a no-brainer. Our current way of doing things is financially debilitating for those shopping on the open market. Moving towards a more affordable, patient-centered system will allow more people access to health care and open the door to more people working for themselves, effectively putting the “free” back in freelance.
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  • Reply Christin August 12, 2013 at 12:35 pm

    Is there anything in there about pre-existing conditions? Just askin’ because well, i have about 100, and I might be freelancing soon.

    • Reply hipstercrite August 12, 2013 at 12:38 pm

      Good question and one I didn’t address. I’m not well-versed in this area. I do know that health insurance can get mighty high for pre-existing conditions, but Obamacare is supposed to put an end to that.

      From an article I found: How will pre-existing conditions like cancer or diabetes be handled under the exchange program? — Paulette Gareau

      Starting in 2014, health insurance plans cannot refuse to cover you or charge you more just because you have a pre-existing health condition.

      Being sick won’t keep you from getting health coverage. An insurance company can’t turn you down or charge you more because of your condition. It can’t refuse to cover treatment for pre-existing conditions.

      This is true even if you have been turned down or refused coverage due to a pre-existing condition in the past.


      • Reply Christin August 12, 2013 at 12:44 pm

        Is it weird that I feel like that’s too good to be true? I know that through an employer, they rarely check into preexisting conditions, etc but when I’ve ever applied for myself it’s been rather extensive and definitely reflected in the premiums. I just don’t know where those extra costs, to insure someone who may be more sick than others, where go to, you know? Someone has to pay for them.

        • Reply hipstercrite August 12, 2013 at 3:55 pm

          I understand your skepticism. They usually don’t get into the pre-existing questions part until you’re deep in a phone conversation with them. I would maybe check with a carrier you don’t want to go with, see if you can get coverage or see how much they charge. Once you have an idea and want to go forward, then call the carrier you WANT to go with? Does that make sense?

  • Reply Mai August 12, 2013 at 3:50 pm

    Bless for you this info! I pay over $200 for BCBS and use it for the basics. When did you cancel your BCBS? Did you have a grace period or a time when you were uninsured between your new and old policy?

    • Reply hipstercrite August 12, 2013 at 3:56 pm

      I cancelled my BCBS the same day I called Humana. Humana approved me and sent me paperwork that I had two days to sign off on. Within those two days, I called and cancelled BCBS which took only 2 minutes. I hadn’t paid for the next month of BCBS yet, so I had no need to be refunded.

  • Reply Tim Elliott August 14, 2013 at 7:33 pm

    I quit my job with full benefits to start freelancing. I started a side business offering SEO services on seoclerks.com and it took off. Enough that I was making more by the time I woke up (in sales) than I would all week at my job, so I quit.

    The hardest part was finding insurance! It drove me crazy because I felt I needed it for my wife and daughter. We went with an agency who got us tangled up in a 4 month insurance fiasco but we finally got it after that long wait…. and we’ve never used it once. 😐

    Is it worth it paying the outrages fee per month? I’m unsure. I think it can only be justified in the event of a major medical expense and then it is worth every dime.

    • Reply hipstercrite August 16, 2013 at 1:47 pm

      Hi, Tim! Thanks for sharing your story! It’s a great question. I agree that it may not be worth it if, knock on wood, nothing major happens, but I hear time and time again people accumulating terrible debt or not getting adequate treatment because of their lack of health insurance. Plus, with Obamacare we will have to have it in order not to be penalized. I know I sleep better at night knowing I have insurance (I’m also a worry-wart).

  • Reply » Health Insurance September 7, 2013 at 12:38 am

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  • Reply Clarisa September 30, 2013 at 10:00 pm

    A big thank you for writing this blog! I’m currently freelancing and working part-time, and I totally hate thinking about not being insured!

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