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While a good premise, I don't believe it holds up. Healthcare is just one facet.

Far and above is the lack of paycheck which encompasses healthcare.

"If money was no object, what would you be doing?" The question isn't, "if you had your healthcare covered, what would you doing?"

The answer to the first question effectively never, "working for my current employer". For the 2nd question, it's still plausible.

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This. Health insurance is indeed quite expensive in the US but, from a self-employment standpoint, it is just a cost like any other. You can get good health insurance for a family of 3 (middle aged parents of a teenager) where I live in the US for around 25k-30k/year, including the out of pocket costs for moderate usage. This is less than rent for said family in a lot of the big US cities.

Nobody wants to "pay rent twice", and it can certainly be a lot harder to stop working when you have a big recurring expense like that, but it's possible to plan for it. Depending on the business you're getting into, it won't be your top expense.

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