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, let’s 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, but from getting through challenging health situations, like overcoming tick-borne infections in my late 20s, visiting the emergency room four times in Mexico due to a parasite, getting an emergency tooth extraction during Covid lockdowns in Spain, and being bitten by a dog in Taiwan. I don’t wish these experiences on anyone, but having gone through them and survived, I have evidence that in most parts of the world, you’re likely to be okay with most health issues. These incidents forced me to take ownership of my health on my terms. When doctors were confused, it pushed me toward self-reliance and accepting that some risks can never be fully eliminated. The book Designing Your Life describes this as a gravity problem — a fact of life we must accept. Behind everyone’s health worries, which may or may not be fully solvable, are financial worries, especially in the U.S., where they are very real. Health insurance should theoretically protect us. It was created to do so. But over time, it has become a complex financial instrument that often adds layers of unnecessary costs. Our healthcare system is a tangled payments-layer mess, and industry players often resist transparency or change, maintaining the status quo for profit. Despite promises of reform, little has changed. Price transparency remains elusive, and the system seems designed to confuse patients and maximize revenue. Shopping for services isn’t straightforward, and many hospital systems actively block transparency initiatives. Since 2005, the system has become more expensive without corresponding improvements in value. Obamacare improved access for entrepreneurs through exchanges, which was a positive step, but since then, costs have continued to balloon, incentivizing overuse and price hikes. Many doctors have lost autonomy, absorbed into large healthcare systems that control prices and decisions, often unaware of actual costs themselves. Arming Yourself: Specific Hacks & Strategies Given this complex landscape, I’ve spent considerable time hacking my way through it, learning how to navigate and even leverage the system to my advantage. Here are some practical tips I’ve found useful: Prescription Length Limits: Insurance often limits prescriptions to 90 days. Paying cash can waive this limit. Ask your pharmacy to refill prescriptions simultaneously or fill prescriptions at different pharmacies to avoid detection. Part-Time Class Insurance: Some universities offer affordable insurance for part-time students—research options at local colleges or universities. Cash Prices for Prescriptions: Many pharmacies offer cheaper uninsured prices. Use services like GoodRx to compare prices and ask pharmacies about cash discounts. Ask for Cash Prices Everywhere: Always inquire about cash