If you’re billing at $300/hr and working when and how you want, it actually seems immensely disingenuous to try to associate with the sympathies for people stuck in the gig economy con job the tech tyrants have been imposing on society as a kind of excuse why you couldn’t manage to fill your consultancy pipeline.
I also guarantee he could have gotten health insurance, he just did not feel comfortable paying the roughly $1,000 to $2,000 per month it would have cost because his business pipeline was not full of work consistently.
People don’t realize just how much health care costs, regardless of whether it’s American employees who don’t realize the employers contribution is about 4-5 time what they pay monthly, or the worshiped and beatified “universal healthcare” that is “free” in Europe where massive taxes are paid to augment the also massive individual monthly cost taken out of people’s paychecks.