First and foremost, if you are a PhD thinking about jumping to a prep school, it's not unusual for you to panic, and wonder if you are making a horrible mistake. So far I have melted down twice in the last month. "I don't want to teach at a prep school," I complained. "I want to teach at a small, wealthy, liberal arts college, with pre-tenure sabbatical. Iwant to make $65k as an assistant professor, and $80k as an Associate. I want a 3-2 teaching load with no class larger than 20."
The problem, of course, is that I had fallen into the trap of comparing my real-world options with my fantasy-world options. I wrote a version of this elsewhere, but it is stil true:
I think that it is extremely easy to get addicted to being on the market in the way a gambler is addicted to searching for the Big Score. There is the anticipation as the jobs are posted/cards are dealt, the excitement as you mail an application/place a big bet, and the disappointment when you are rejected/lose the hand.
You might always lose, but there is also no reason to leave the job market or get up from the table. Why? Because there's always another hand to play or another year to apply.
The addict's challenge is to realize that while there is some truth to the saying, "You can't win if you don't play," it is almost as true to say, "You can't win if you do play." But the panicky voice in your head is only telling you the first story, and that story is for suckers.
So what to do when you panic? First, do nothing. Don't call your rep, don't email search committees. Just let the panic be. Then, breathe deeply, and remind yourself why you are making this move: You will have better students. You will make more money. You will have a choice where you live. You will be able to send your kids to an excellent school for pennies on the dollar. Repeat.
If you need to, to read this thread: http://chronicle.com/forums/index.php/topic,66956.0.html It was my original cris de coeur when I started down this road, and it might help remind you why you did so as well.
Then, have a drink or two. Get a good night's sleep. See where things stand in the morning. Have any of the things that made you want to leave academia changed? Have any of the attractions of prep school teaching (or whatever other career you have selected) diminished. Probably not. Then carry on.