> why can't I work 20 hours as a programmer, and 20 hours as a tree-planter, or teaching rock climbing to high school kids, for maybe 55% of a programmer's salary?
Health care is mostly not insurance, is tied to employment for a purely historical reason, and is precisely the largest issue preventing people from ditching safe but boring jobs and going after something new.
(And YC clearly understands this: look at the age of YC founders. Young, healthy, able to depend on someone else's healthcare or none at all for a year or so. Oh, and no mortgage.)
This is a standard answer that everybody gives, but for the most part it just isn't true. People hear the occasional horror stories and assume it is difficult for everybody without trying to source it themselves. I am leaving my current job at the end of the month and will be freelancing/starting my own business. I bought health insurance with no problems. I was approved in less than 2 weeks. I am married and have 3 small children and pay a little less than 300 a month.
You are fortunate not to have any pre-existing conditions in your family and i wish you not to ever have any. If you were to develop a serious condition while on individual or or a small business(<10 people) group plan, you will eventually be priced out of your insurance by your carrier raising your rates. This risk is generally spread out over large group such as a big company with several thousands of employers such as Google and thus their medical costs are same regardless of your medical history.
Furthermore once you or your family member develops a "preexisting medical conditions", you may not be approved next time you decide to to from corporate plan to individual. My wife was denied by one carrier for having chronic migraine for which she was taking prescription drugs and not seeing a doctor more than once a year.
With a current state of healthcare/insurance, I will only be able to leave my current employer and start a startup for as long as COBRA and CAL-COBRA allows. After that I will be forced to either join a larger company or have my family be without healthcare if a carrier decided to deny us coverage for preexisting conditions.
> You are fortunate not to have any pre-existing conditions
THIS. Although in many states there is a high risk pool that you can sign up for, when insurers deny you. I know someone who's done this in California and while there was a 6-9 month waiting list, and the coverage wasn't great, it was much much better than no coverage at all.
Health insurance.