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 managed multiple acute health issues independently 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. Our obsession with “insurance” often prevents us from asking deeper questions about what’s possible and what we truly want to solve regarding healthcare.
Here are some insights I’ve gained over the years about the system, specific hacks, and various learnings.
Deconstructing the “Safety Net” : Thoughts on the US Healthcare System
Most of my feelings of safety and comfort haven’t come solely from having health insurance but from overcoming challenging health situations, such as :
I don’t wish these experiences on anyone, but surviving them has shown me that in most parts of the world, you’re likely to be okay with most health issues.
These incidents pushed me to take ownership of my health on my terms, fostering self-reliance and acceptance 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 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, but over time, it has become a complex financial instrument that often adds layers of unnecessary costs. Our healthcare system is a tangled web of payments, with industry resistance to 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, costs have increased without corresponding improvements in value. Obamacare improved access through exchanges, a positive step, but costs continue 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 leverage the system to my advantage.
Here are some practical tips I’ve found useful :
Any other hacks?
I’d love to hear from others about strategies that have worked for you.
Every month, I detail my financials. You can see my full spreadsheet here, including income and expenses for specific months.
About Paul Millerd
Paul is a writer, creator, and curious human passionate about reimagining work. He published The Pathless Path in 2022.
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