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Americans, it is said, dread death and taxes. Neither is pleasant, it’s true. But if you pay attention as the year goes on, your tax bill (or refund) shouldn’t be much of a surprise. I’m self-employed, as is my spouse, and if we stay on top of our quarterly estimated tax payments, April 15 is not very painful.
Dec. 15, on the other hand, is a day of uncertainty and fear — that’s the day that freelancers like us roll a ball onto a roulette wheel, but one that’s spun bewilderingly by the state government, the federal government and health insurance companies. When the ball came to rest on our application, the result was that our monthly premiums will sextuple on Jan. 1, 2026. Just imagine if two weeks before your taxes were due, the IRS told you that your rate was going up six-fold.
Courtney is a photographer and yoga instructor; I’m a writer and adjunct professor. We’ve both had corporate jobs in the past — she at a newspaper, me at a publishing house — but we followed our dream into self-employment after the kids were out of the house. We make a decent living, with the ups and downs of income that are inherent to the freelance life. We’re OK with that, and we adjust our expenses to match our income. We chose freedom over stability, with no regrets.
We hear all the time from politicians that America is a land ripe with opportunities for entrepreneurs, that launching out on one’s own is part of what makes America great. But beneath their platitudes, those same elected officials refuse to act. They acknowledge that the health care system is broken — they even run in elections, promising to fix it — yet they never do.
Health care hasn’t always been tied to employment. That marriage happened in the early 1940s when, during World War II, companies could not afford to give raises, so instead they started offering health insurance as a benefit. By 1954, the union was consummated when the IRS permanently ruled that health insurance from employer to employee was not considered taxable income.
Three-quarters of a century later, corporate America may not like administering health plans, but it still clasps those golden handcuffs on its employees. If one of my friends or my children asked about leaving their 9-to-5 to pursue self-employment, I would warn them about the stress and expense of acquiring health insurance.
