[vidarh]

I've only done the latter in the form of being brought on as a contractor at (high) contractor rates but with the understanding they'd prefer to have me join full time, at a time when I was already doing contracting and had other clients in parallel covering parts of my costs. In that situation I was not taking on any more risk than I had already chosen (and planned for) by contracting, so it was fine.

It's the only kind of context in which I'd ever consider the "we don't know so let's try it" approach.