Freelance Tax Considerations for Health Insurance Open Enrollment

If you’re new to the freelance world or just looking for some tax help in the insurance marketplace, read on!

Tim Gordon
4 min readNov 10, 2021
Photo by National Cancer Institute on Unsplash

We’re nearing year-end, which can mean only one thing: year-end health insurance enrollment!

As an employee, I always looked forward to the health insurance packet with a mixture of dread and excitement. Dread, since the prices were rising at ridiculous rates year after year (which have since, thankfully, leveled off). Excitement, since I’m a numbers nerd, and it was time to get everything tweaked for a new year.

I wrote last week about one of the big downsides of the freelance world: no built-in benefits. So this week, naturally, I’m trying to figure out my own benefits. Except instead of calculating how much of my raise will be eaten up by higher premiums, I have to determine how much of a freelance rate I have to make to keep the doctor visits flowing.

If you’re in the same boat, here are some considerations you should factor into your own budget calc.

Only Deductible If There’s No Employer Plan

I complained about this last time: as a freelance individual, you can deduct your private health…

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Tim Gordon

Accountant, Professor, Entrepreneur. Loving my household of struggles (seizures, anxiety, dysautonomia, autism, dysgraphia) while training a poodle service dog