Dice Rolling

Natural Crit
I did something fairly drastic today.
Since October of last year, I've been working on a contract basis for a company here in the Austin area. For various reasons, that contract has been extended a number of times, and here we are in August.
I gave notice today that I would not be seeking a further extension of the contract.
From the outside, this looks like a particularly stupid move.
There's some justification for that. It's not the best job market in the world out there. The legal job market in particular is tough, especially in Austin where we have a large number of attorneys for the available jobs, and more coming every year. I don't have something else I'm jumping into. It's an absolute leap of faith.
I know. Crazy.
But necessary. For lots of reasons. Necessary.
Every now and then, it's necessary to roll the dice. To take a risk. Usually it's a calculated one, but sometimes it really is rolling because your gut says to roll. Or the Great DM in the sky suddenly says "Roll for initiative…" and then life drops in the pot.
So, what stat am I rolling against? INT? (Not very smart to leave when you don't have the next gig lined up.) CHR? (Who do I have to charm to get the next gig?) CON? (Because it's a gut check? And did I succeed or fail?)
WIS?