Are you aiming high enough?
Your soul should fetch a goodly amount from the Devil. After all, people are selling their souls on eBay for upwards of $475.00 (I’m not making that up). Make sure you ask for all of it—fame, fortune, love, happiness, and maybe a lifetime supply of DoubleStuf Oreos. Go for broke. You can always give up the Oreos during negotiations.
How much do you really know about Satan?
Sure, you probably know the Devil went down to Georgia that one time. Or that a friend of the Devil is a friend of yours. But if the entirety of your information on the Prince of Lies resides in old Charlie Daniels and Grateful Dead tunes, you might want to bone up on your Beelzebub knowledge before entering a contract with him. Find a nice, chatty Catholic priest, perhaps. Or read a book. Maybe the Good Book.
Do you have a good lawyer?
If we’ve learned anything from Faust or “The Devil and Daniel Webster,” it’s that the Prince of Darkness is a tricky little bugger. Before you sign a contract with him, make sure you have a competent attorney review all the paperwork. Don't chintz out on this important step. Might as well go for the best money can buy—after all, you’ll surely be able to afford it once the deal is done and Satan bestows a ton of money on you. (You ARE asking for money, right?)
What can you expect, weather-wise?
Perhaps the most tempting aspect of eternal damnation in Hell is the heat. The glorious, glorious heat. (I live in New England. The thermometer peaked at -2 degrees today. Brimstone sounds darn cozy right about now.) But a quick review of Dante’s Inferno might have you thinking twice about taking up residence in Hell. For instance, did you know that there’s no guarantee you’ll wind up somewhere warm? Dante describes the third circle of Hell, where all the gluttons hang out, as being full of vile slush produced by never-ending icy rain. Icy rain. Brr. And the last circle of Hell? You know, where the worst people go (like maybe those of you that sell your souls for personal gain)? They’re all encased in a frozen lake. Some of ’em are even being chewed on by the Devil himself, but just enough to make them bleed, not enough to warm them up with satanic saliva. Doesn’t sound warm and brimstony at all, does it?
Are you sure eternal damnation is the right choice for you?
If you’re still hell-bent (har har) on selling your soul to the Devil, make sure you’re making the right choice for you. Are you good at handling brutal torture, or does that sound like something you might not enjoy for all eternity? Is fame and fortune really worth being gnawed on by Satan while being encased in an icy lake? Wouldn’t it just be easier to play the lottery or buy your own DoubleStuf Oreos on occasion? And don’t delude yourself—once that contract’s signed, it’s signed. Don’t count on outsmarting Lucifer—if you can’t even outsmart your four-year-old nephew at Candyland, you’re not going to do well against the Prince of Lies himself.
Selling your soul: there are probably better options out there.