Dr. Freelance, I have a pre-existing health condition, and I am considering taking a part-time position with one of my clients as a way of securing affordable insurance. I haven’t made my final decision, because it feels like I’m “giving up” if I’m no longer freelance-only. What’s your opinion? — 100% 1099
100% 1099, I understand your pride in being full-time freelance. That pride, however, needs to take a back seat to the more practical matters, which are 1) your health and 2) your overall financial well-being. I’m going to assume that you’ve done your homework and exhausted all of the possible options of self insurance. And I’m going to assume that this client is someone you enjoy working for and respect.
The reality is that freelancers exist in a wide spectrum of formal and informal arrangements, and one size doesn’t fit all. Over time, I’ve been on COBRA, self insured, insured through a part-time gig, and currently through my wife’s employer–and my healthcare plan never affected how I perceived myself as a businessperson. It’s just a bill, eh?
So, if you’ve cut yourself a good deal, I say go for it. When the time comes that you have a healthier income or another healthcare insurance option makes more sense, you’ll have another decision to address.