Well, he would probably experiment with other things first. If all else failed, he would become a dictator.
That is probably everyone's back up plan.
Week 1: "If I can't get that job as the head of urban planning, I'll think of something with less responsibilities."
Week 5: "Oh well, I'll apply for this job instead. I guess being hired as a supervisor in the maintenance department wouldn't be so bad in this economy..."
Week 17: "If they won't take me on as a janitor, I think there are no good choices left."
Week 45: "All right officer, I learned my lesson: no more selling illegal booze in the alley."
Week 68: "So panhandling didn't work out for me, and someone stole my shoes."
Week 87: "Man, I thought I could sell my organs for a bit of cash, but appears I ruined them in my panhandling days."
Week 109: "And now they needed to amputate my left leg as well. That's it! Can't help it, becoming a dictator is the only way to go."