I'm A Full-Time Freelancer, And Here's How I Navigated Health Insurance

© vectorfusionart / Adobe Stock

woman freelancing

© vectorfusionart / Adobe Stock

AnnaMarie Houlis
AnnaMarie Houlis
July 14, 2024 at 12:57PM UTC
“I travel to face my fears,” Valerie Stimac, 30, wrote on her travel blog, Valerie and Valise, in a 2015 post. “For me — and maybe for all travelers — there’s a certain rush when realizing you’ve done something you perhaps didn’t think you couldn’t before… I look back most fondly on those travels where I’ve been the most changed.”
For Stimac, however, traveling doesn’t only change her; rather, it largely defines her. Upon moving back to the States after earning her MBA in London in 2013, Stimac was keen to find a constructive hobby while unemployed. Enter: Valerie and Valise. Aptly titled, Valise refers to her leather weekender with which she prefers to traverse the globe. She made the decision to focus on her blog — which has since amassed more than 80k followers across her social channels — for about one year until she had the opportunity to write for Lonely Planet; that’s when her freelance career really launched. 
To date, Stimac has traveled some 26 countries and writes almost exclusively about travel. She has bylines in major travel publications spanning Lonely Planet, AFAR, MapQuest, Go Overseas, Matador and more. For most people, making the decision to delve into freelance full time isn’t an easy one — perhaps it’s even a fear many of those on the fence face, and one that travel might not be able to assuage. 
While Stimac has built a reputation for herself as a travel writer — and the career does promise flexibility, creative authority to some capacity and autonomy — freelancing is no easy feat. Most freelancers are readily aware that, atop innumerable pitch emails and the occasional need to chase checks, working for oneself also means fending for oneself with regards to pricey necessities like health insurance. But before recently accepting a position as a managing editor for one of her former clients, Go Overseas, Stimac had pulled off freelancing full time for nearly three years in her late 20s.
"The startups I’ve worked at have always provided health insurance, plus dental and sometimes vision,” she says of her jobs prior to freelancing. "I always just used those benefits because they were available, and didn’t give it much thought.”
When Stimac fell into freelancing full time, she had to give health insurance thought. And because she did just that, we’ve asked her a bit about the process. If you’re looking to freelance but are apprehensive about giving up your benefits, consider this advice from a woman who’s been there, done that.
When you first began freelancing, how did you handle health insurance?
Valerie Stimac: This might not be the most responsible answer, but I didn’t have health insurance at first. I did the math to compare the ACA penalty for the months I would be uninsured with the cost of premiums, and determined I’d rather ‘risk it.’ Luckily I was both young and healthy, and had a good low-cost clinic in my neighborhood where I could pay cash when I got sick and needed to see someone.
Did you use any resources to scope out your options? If not, how did you know what options were available to you?
VS: Prior to getting my MBA in 2012-2013, I worked as a mental health counselor in the healthcare system in Indiana. In that role, I spent a lot of time interacting with insurance companies as a provider, so I learned the ins and outs of how health insurance actually works. I learned how to compare the benefits within a plan as well as the ‘total cost’ of a plan each year, assuming you need to use it. That gave me a good framework to do research on my own when I started freelancing.
I used the Washington state healthcare marketplace, WA Health Planfinder, [where I was living at the time] to start my research, but I actually ended up going directly to an insurance provider to compare plans on their site once I figured out which provider had the most comparable and affordable plans and best coverage for my area.
Did you qualify for premium tax credits or other savings? Or did you qualify for free or low-cost coverage through Medicaid or other programs?
VS: I did not. Since I didn’t get insurance for a few months when I first started freelancing, by the time I applied, my freelance income was high enough that I didn’t qualify for any assistance.
How did you ultimately decide on a coverage plan, and what was it?
VS: I decided on a plan based on the combination of three factors: the deductible, the annual cost of all premiums and the amount of coinsurance. In particular, I added together the annual cost of the premiums and the deductible to compare between programs.
I also keep a close eye on two other benefits: mental health coverage and maternity/reproductive care. As a woman and with a history in mental health, these benefits are especially important to me, and I want them available in any health insurance.
In your opinion, what were the pros and cons of each category: bronze, silver, gold and platinum? How did you decide which category was right for you?
VS: I’ve typically gone with the silver or gold plan each time I’ve had to choose insurance. I often find that bronze has a great premium but huge deductible (meaning, if you did need to use the insurance for an emergency, which, at 30, is probably the most likely use I’d have for insurance, you’d end up paying more than other plan levels). Platinum usually has premiums that are just outside of my budget.

Between silver and gold, I consider the benefits I mentioned above and the ‘total cost’ (deductible + premiums) to make my final decision.
If you don’t mind sharing, how much did you end up spending each month on health insurance, and what were your deductibles like?
VS: My premiums were typically in the $220-$250 range. Deductibles ranged much more widely, from $1,500 to $7,500.
Did you have any health issues or concerns that required medical attention during this time? If so, did you find that the coverage plan you chose was adequate in getting you the care you needed?
VS: My primary needs have been preventative care and reproductive health as a woman, which is why I always keep an eye on the coverage for those benefits and what the coinsurance will be.
What were the biggest challenges in navigating the health insurance space?
VS: There are way too many choices. Having worked on both the provider and consumer sides of insurance, it shouldn’t be allowed to be this complicated for anyone to get health care. I think that was the vision for ACA in its initial stages, though it obviously hasn’t played out like that — now it’s more of a penalty for individuals to not have insurance than an incentive for insurance companies to create better plans for their customers. These incentives in general are all wrong in health insurance in the U.S.
What is one thing you wish you knew before delving into your health insurance options and ultimately deciding?
VS: It took me too long to realize that the lowest premium does not mean you’re paying the least. The older you get, the more you realize that emergencies and health issues are a reality, and the deductible and co-insurance are so important for figuring out your total cost for any plan.
What is the biggest piece of advice you have for anyone interested in freelancing full time but afraid of how they’ll handle their health insurance?
VS: Don’t let health insurance be the barrier to creating a life that has more flexibility and freedom (which freelancing typically does!). Start by setting aside a budget item for about $250 per month, and you can probably find a plan that matches that once you start freelancing. Spend far more time worrying how to get good clients and get paid on time — those are the factors that make freelancing a successful, enjoyable professional path.
AnnaMarie Houlis is a multimedia journalist and an adventure aficionado with a keen cultural curiosity and an affinity for solo travel. She's an editor by day and a travel blogger at HerReport.org by night.

Why women love us:

  • Daily articles on career topics
  • Jobs at companies dedicated to hiring more women
  • Advice and support from an authentic community
  • Events that help you level up in your career
  • Free membership, always