I think it's possible, but that's only because the gov't system is fucked up.
My mother is receives SS Disability, as she is only able to work to a fraction of her former capacity, after multiple surgeries to remove brain & spinal tumors. She doesn't like it, but the government has taken away her options. For years, she was a responsible individual who purchased disability insurance through work, in addition to the regular percentage taken by the federal government. Her retirement savings were the nest egg; the disability plan the emergency backup. As it should be.
She wasn't able to work full time after the first round of surgeries and chemo, but the disability insurer worked with her to keep her income steady during the part-time return to work. After a year or so, she was back. No problem, everyone happy.
Round two - She was unable to back to work at all for a while. Social Security steps in, and the disability insurer only pays the amount between what SSA pays, and her set percentage. Everything is still fine, until Mom wanted to go back to work. The SSA, not the disability insurer, has requirements. She can't do the same job part time which she used to do full time. She can't work over a set amount. She cannot make more than a set amount. If she goes over set amount, SSA stops paying. At this point, the disability insurance could kick back in, to make up the difference like when she first became ill, wouldn't you think? Not so. Against the rules. She'd lose everything.
If anything, her dealings with this over the last 10-15 years have made her more receptive to liberty, especially in financial matters. She's still a right wing conservative on the moral issues, and I don't see that changing anytime soon. But it's a start.