Why would you have to start at the bottom again? Do you hate your particular job, or do you hate the whole idea of what you do for a living?
If you're thinking of completely changing careers, my advice would be to do it soon.
Of course, that should be weighed against:
1. How much cash is in that "reasonable sum"?
2. How soon is "in a little while"?
If you're talking about going back to school, the cash will come in handy.
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If you want to avoid 95% of internet spelling errors:
"If your ridiculous pants are too loose, you're definitely going to lose them. Tell your two loser friends over there that they're going to lose theirs, too."
It won't hurt your fashion sense, either.
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