How I selected my $1020/month health insurance

Every month, I’ll spend $1020 in premiums for health and dental insurance in 2026. For readers with an employer subsidizing your plan, you might think that only a portion of this $1020 will be my responsibility. But I have some sad news: all of that is on our family. Even worse, millions more people are on the brink of losing their healthcare due to unsubsidized costs.

Today, I want to tell you about being self-employed, how I chose my plan, and how many of us will likely gamble with our health in 2026.

When I moved into private psychotherapy practice in 2020, I only needed a computer and Zoom. “Hanging up a shingle” was more accessible than ever before.

I had nothing to lose. I started the practice while at another group practice, benefiting from their health insurance plan. It was slow, and I questioned whether the practice would ever work out.

A year later, some actual revenue was coming in. In year two, I made more than I ever thought possible. I was sucking on the free market teat and getting fat while doing so.

And then I got sick last year. Like, really sick. The kind of sick where I wondered if I'd ever be okay again. My medical bills were over $100,000 before insurance coverage. Every coverage line of my policy was maxed. The health insurance company was calling me to inquire what was happening (i.e., calling to see if I’d stop going to the emergency room anytime soon).

Self-employed with no sick leave or vacation days, the loss of income then followed. I couldn’t work part- or full-time for about two months. From flying high to nothing. The best and worst of the free market — in a couple of weeks time. After that, shopping for 2026 coverage felt different — less like comparing plans and more like preparing for disaster.

My wife and I sat down and reviewed our healthcare “choices.” Every year, I’m optimistic: maybe my children and I can join her plan! She’s completely subsidized as an individual — amazing! — but they offer no subsidy for families. No matter how we square the math, it’s always way more expensive to be on her plan. Her plan would be at least $1300 per month. The implicit message is that you either need to be poor enough to go on Medicaid, employed by another company with benefits, or rich enough to not give a damn.

Self-employed, I fall into this healthcare trap — responsible for it all and needing to cover our children, separately.

What choice do we have but to check Healthcare.gov for a cheaper plan? The government site highlights premiums, out-of-pocket maxes, co-pays, and estimates for general procedures. The documents would likely take the average person days to critically analyze everything. This is a system designed by healthcare companies for their profits, not for easy understanding.

I was stuck in some purgatory of decision hell about which of the hundreds of plans to “choose.” Once again, I turned to Claude AI, feeding it PDFs and asking it to analyze which plan would work best for us. It’s a great technological trick, but really symptomatic of a system failure.

Eventually, we selected the “Better Together HMO Bronze 6500 Ded/8750 MOOP.” Rolls right off the tongue! Decoding the title, this equals $6500 in deductibles and a $8750 max out-of-pocket before the insurance really starts kicking in. Mind you, we’ll be spending about $1000 per month either way.

No developed nation accepts this preposterous process. Can you imagine how much productivity, home life, and joy is lost to these “choices?” Other countries have long moved on to socialized healthcare and other government-led options. They’re saving money, but more importantly, they’re saving time by not choosing. Everyone affords the care they need, when they need it.

In fact, I increasingly wait until I visit my in-laws in Canada for health and vision care. Recently, I got my eye exam done in Ontario, Canada for $65 USD — at least 50% less than in the States. I repeat, this is without health insurance in Canada — as a foreigner!!! This is nonsense.

Millions are staring at losses of federal subsidies for their healthcare. Some are looking at their premiums going from $180 to $1200 per month!

There’s no way people will be able to afford this year-over-year increase. Many will go without or be underinsured — rolling the dice in 2026. Gamble and stay healthy all year long, and you might take home a $10000+ jackpot. Bust, and you’ll be on the hook for your medical bills in full — likely bankruptcy, too.

We were here before. Prior to the introduction of Obamacare, people could be charged more for their personal health — pre-existing conditions could make you uninsurable or a fortune to insure. And citizens could opt-out of carrying healthcare at great risk. In 2019, the individual mandate's tax penalty was eliminated, removing the last incentive for healthy people to keep insurance. And with skyrocketing premiums, how could anyone afford this?

As Americans, we seem to be using "Cut off your nose to spite your face" as inspiration for policy. We'll save money today by cutting FEMA and the Department of Education. This is the same short-term thinking behind letting healthcare subsidies expire. We are saving today, at risk of tomorrow. And tomorrow always comes.

In the short term, we need to ask our representatives to support continued subsidies for 2026. People have already selected plans. Payments on plans are coming due for the new year. Long term, we need a real government plan available to everyone, regardless of income, employment, or health status.

We are killing ourselves, drowning in the illusion of “choice.” When our only decision is dying in poverty (without healthcare) or living in poverty (with healthcare), we’ve failed.