Maybe I'm an oddball, but I've always thought this: if a cool company wants to hire me but isn't sure, give me a 3-6 month fixed contract and LFG. There's zero doubt in my mind it would work out. And if not, so what, I'll be okay.

Today I'm 45 with family and have a fancy VP title, but I would have no problem to do this for an interesting role at a cool company.