Hacking US Healthcare: A Guide to US Healthcare for Self-Employed People

Over the last eight years, I’ve directly experienced the US healthcare system from multiple angles.

As a self-employed person, I’ve had health insurance in four different states (NY, MA, CT, TX), been uninsured for multiple years, interacted with healthcare systems in Mexico, Taiwan, Spain, and Portugal, and have had multiple acute health issues I’ve had to figure out on my own when doctors were confused or lacked answers.

Since 2012, I’ve also had ongoing chronic issues. It’s safe to say I’ve become obsessed with the healthcare system and learned quite a bit.

I share this because many people’s worst fears about being self-employed involve not having health insurance. I think this is somewhat of an illusion, the feeling of safety without actual safety. And our obsession with “insurance” keeps us from asking deeper questions about what’s possible and what we really want to solve regarding healthcare.

Here are some things I’ve learned over the years about the system, specific hacks, and various other learnings.

First, lets take a step back and deconstruct the “Safety Net”: Thoughts on the US Healthcare System

Unfortunately, most of my feelings of safety and comfort haven’t come from simply having health insurance, they’ve come from getting through challenging health situations, like overcoming tick-borne infections in my late 20s, having to go to the emergency room four times due to a parasite in Mexico, getting an emergency tooth extraction during Covid lockdowns in Spain, and getting bitten by a dog in Taiwan.

I don’t wish these upon anyone, of course, but having gone through them and survived, I have some hard evidence that in most places in the world, you’re going to be okay with most health issues you might deal with.

These incidents forced me to take ownership of my health on my terms. Because doctors were often confused about what was happening with me, it forced a self-reliance and, more deeply, an admission that there is just some risk I will never be able to eliminate. A really good book, Designing Your Life, calls this a gravity problem – something that will always just be a fact of life.

But really, behind everyone’s health worries, which may or may not be able to be solved fully, are financial worries, which in the U.S., sadly, are real.

Theoretically, health insurance should protect us. This is what it was created to do. But in the meantime, it has morphed into a complex financial instrument that is far beyond protecting people’s downside risk. In practice, our health insurance system is a weird payments-layer mess for the entire healthcare apparatus. It is how the industry “works,” and no one really knows how to transition out of it, so everyone just continues maximizing their local gains.

Politicians always talk about fixing the system. It never happens. Every president since Obama has promised price transparency, yet all have failed to deliver. The healthcare industry seems optimized for patient confusion and growth. You can’t just shop for services like you might be able to between Walmart and Macy’s. The biggest hospital systems are actively spending millions if not more trying to stop this sort of thing from happening.

As a self-employed person, 2025 is far better than it was in 2005. Before then, you couldn’t even get healthcare if you were working independently, or you’d have to find some sort of loopholes, and even if you did find a policy, they would be incredibly expensive. People talk about how bad Obamacare is, and there are definitely issues, but many of these problems were already embedded in the system. Offering direct health insurance to individuals through exchanges, however, was game-changing for people who work independently. Direct healthcare exchanges have been amazing for entrepreneurship, and we should consider more creative ways to encourage business development.

But since Obamacare was passed, the system has continued to balloon in cost without an increase in value. Insurance plan subsidies have increased, expanding even more under Biden. This is a feel-good policy; it sounds great in speeches but has probably made the system worse off. It has meant that people with low incomes are getting “free” health care, There has been a bigger incentive for insurers and providers to consistently raise prices higher and higher. These guaranteed payments push almost everyone in the system into trying to get things covered by insurance, too, so that they can get on this gravy train.

On top of this, many doctors have become middle managers, disempowered to make decisions. We often think of them as independent actors, but in practice, doctors are not entrepreneurs, even if they should be incentivized to behave like them. Unfortunately, many have been absorbed into giant healthcare systems and don’t have much autonomy regarding prices and finances. They’ve been stripped of this power. You can ask doctors what certain procedures cost, but they often won’t know.

Arming Yourself: Specific Hacks & Strategies

All this is to say, I’ve had to spend a lot of time hacking my way into first figuring out the system and, second, trying to hack it.

After going through many of these approaches, I hope that they give you more confidence that healthcare may not be as expensive to afford on your own and that there are many loopholes to hack the system, which might give you more confidence in pursuing a more entrepreneurial path.

Here are some specific things I’ve learned that might help you navigate this landscape:

• Prescription Length Limits: The limit for prescriptions with insurance is often 90 days. This restriction is waived if you’re not using insurance. This means you might be able to request all your refills at once from CVS if paying cash. Ask! You can fill two prescriptions at the same time at different pharmacies because they’re not plugging it into an insurer, so no one will know you’re refilling two at the same time.
• Take a part-time class for insurance: Some universities offer class insurance to part-time students. This can be obtained at the student price for as little as one credit. There used to be a site for this, but I can’t find it anymore, so do your own research.
• Cash Price for Prescriptions: Most pharmacies have a policy against informing customers that prescription medications may be cheaper at the uninsured price (a CVS representative disclosed this to me years ago). For many common prescriptions, the uninsured price is cheaper. This will surprise many people. You can always ask the pharmacy to run a discount card, or you can bring your own found online using services like GoodRx. GoodRx is always a good site to check what different pharmacies charge for different insurances. For example, Walmart often offers a price that’s lower than with any coupon card or prescription, so often I’ll just go pick up prescriptions from there while I’m in the U.S.
• Ask for the Cash Price (Everywhere): Many doctors’ offices, hospitals, and medical centers offer a cash price. You can always inquire about this option. However, some offices may not know their exact costs. While you may need to contact multiple providers to determine the actual price, cash payments often amount to only 10% of what they would typically bill an insurance company.
• Shop Around in The US: The U.S. is enormous, and so there are many different providers who are not fully absorbed into this system. You have places like the Surgery Center in Oklahoma that are transparent with their prices and even advertise them on their website.
• Medical Travel is Real: Travel medicine is now a real and viable option for many people. You can look up cash prices for medical treatments abroad, which are often performed by highly qualified, English-speaking doctors and practitioners. The perceived quality gap between U.S. healthcare and medical care in other countries is far smaller than most people think. Living abroad and interacting with multiple healthcare systems has given me confidence that if I really needed it, I would travel abroad for major medical issues. The US still maintains a competitive edge for cutting-edge treatments, but for 99.9% of medical procedures, many parts of the world can provide the same level of care.
• No More Penalty: The federal penalty for not having insurance was removed under the Trump administration.
• State Variations Matter: Insurance programs vary radically from state to state. In 2017, I went from paying $550 a month in New York for a bare-bones, high-deductible plan to $250 a month in Massachusetts for a high-quality HMO plan. Massachusetts is one of the best states for health insurance because it implemented health care reform before other states and has a high concentration of high-quality hospitals. Research your state’s specific market.
• Subsidies Are Generous (For Now): Many people don’t know how generous healthcare subsidies are right now. While I don’t love what they do to the system, they exist. If you have a low income, you might be able to get free healthcare insurance. If you’re quitting your job and your salary will be around $50,000 for the next year, you likely won’t pay much for healthcare premiums. This often surprises people. Check healthcare.gov.
• COBRA is Usually a Scam: COBRA offers an extremely inflated price to continue an employer-based insurance plan as an individual. The prices are so high because insurers can extract more money from employers, who are essentially required to offer these plans. The value available on healthcare exchanges is almost always better than what you’ll get on a COBRA plan. While there are some exceptions if you need specific access or benefits, nine times out of ten, you probably shouldn’t pay for COBRA. It’s a legacy from when self-employed people couldn’t purchase plans easily.
• Insurance Alternatives Exist: There are alternatives to health insurance, such as “health sharing” groups and things like CrowdHealth. These options have been around for a while, especially in religious communities; they essentially pool risk within a community of people. This approach can be an effective way to protect against catastrophic risk. I use this method because it allows me to shop for the healthcare I need on a cash basis while maintaining protection against major health risks.
• The Rise of Direct Primary Care (DPC): Many doctors are becoming more entrepreneurial and opting out of the traditional healthcare system because it has become such a nightmare. They are starting alternative practices, such as direct primary care. This is what I use for my daughter. We pay a direct fee to a doctor’s office, and they offer very high-quality services. While they still accept insurance, they also offer cash payment options with transparent pricing for many services. Pairing DPC with health sharing is often a pro move for self-employed entrepreneurs.
• Insure Kids Separately: You can get health insurance for your children (which is often much cheaper than for adults) without getting health insurance for yourself through the exchange. This is what we do now.
• Strategic Plan Selection: During the annual health insurance marketplace enrollment, you can modify your plans. Since we knew we were having a baby in 2023, we selected a low-deductible plan to reach the limit quickly. This strategy worked out well (even though we’re still receiving occasional bills two years later).
• Qualifying Life Events: Need insurance outside open enrollment? Moving to a new address is a qualifying event that would immediately make you eligible for health insurance in the new state. If you faced a major crisis and needed insurance to avoid significant financial issues, this is something you could consider. There are also many other ways to qualify for insurance, such as leaving the country and returning. You could potentially qualify by booking a short trip, returning, and then applying; research the specifics carefully.
• Prescriptions Abroad: You can get many prescriptions abroad by just going to a pharmacy and asking. As someone who’s lived in multiple countries, I like having things like prednisone and antibiotics on hand. I grabbed some last time I was in Mexico.
• The B12 Hack (Use Caution): One thing I take regularly now is B12 injections due to some unexplained issues. In the US, getting this is expensive. One hack I haven’t used involves getting a prescription for a dog. You can apparently get a 50 mL vial of B12 from Petco for $30 (this could cost 100−100-100− 200 through insurance or direct through CVS). I usually just buy B12 abroad, where it is not something you need a prescription for.
• International Pharmacies: Many people buy prescriptions from Canada and other countries. I don’t advise this, but it’s something people do. Proceed with caution and understand the regulations.
• Self-Employed Dental Dilemma: Dental insurance while self-employed is really bad. You can’t buy a good plan like you can with health insurance. You usually have extreme limits or a 1-2 year waiting period to submit major claims. This is why I almost always do dental work abroad. Dental care in the US is also extremely expensive, and you can find great dentists almost everywhere globally these days. I’ve gotten cleanings and fillings in Portugal and Taiwan, both for less than $75. US Dentists are becoming more corporatized, and the upsells and misleading information about “required” work are out of hand. Another option in the US is direct dental subscriptions, which are becoming more popular; these cover services and skip out on insurance.

Any other hacks?

I’d love to hear from others. What hacks have you tried? What other things can work?