As I was restating my argument for targeted, flexible adult education for the umpteenth time here, it occurred to me that the insurance industry may be overlooking an interesting product.
First, I still assert that the average high-skill worker in the US will have to be retrained for a new career at least a few times in his life, because technology and its attendant productivity increases are likely to destroy the market for his old job. That means that, a couple times in everybody's life, they're going to be stuck with the triple-whammy of having to live off their savings and unemployment insurance at exactly the same time that they'll need to be shelling out money for additional education, which in turn will prevent them from picking up even a part-time stopgap job.
This sounds to me like an insurable event. So why wouldn't the prudent worker take out "career insurance"? For a few bucks a month, you ought to be able to buy a policy that will pay for your educational expenses and support your household should you lose your job because it's become obsolete. I guess you'd have to be fairly clever in how you defined an "obsolete job", but this hardly seems like an insurmountable problem to me.