This is lovely advice for those who live in the distant past, but not particularly helpful today. Depending on your field, unless you turn yourself into solid gold, your first job likely IS your last, and you are not going to write your way to a better school.
I bring up this digression, as I am currently wrestling with the issue of fit on the prep school market. I recently returned from an on-campus visit at Very Old Preparatory Academy - the kind of place that counts Presidents and Senators among its alumni. They have pretty amazing faciliites, more money than God...and lots of traditions and rules. It just didn't feel like a fit.
My dad taught social studies for many years at a progressive (and elite) school. I remember that his classroom was a riot of books, maps, and student projects. Not here. At VOPA, classrooms had a whiteboard and framed posters. They were like a doctor's examination room. I couldn't help wondering how they would react if I piled books around my classroom, or grew my hair down to my ass. (I would not do the last of these, but I still wonder what they would say.)
So what to do?
My dad actually gave me one excellent piece of advice.
I made reference to your uncle being an unhappy as a progressive teacher in a traditional school. I think some people can pull off that, and some schools will allow a measure of radical dissent and even welcome the diversity (perhaps safety valve) that such divergence affords.
If VOPA offers the job, ask them about their comfort with your differences.
So, where does this leave me? Probably nowhere until I get an offer, if I get one.
But then the question I have (for you) is which proposition is more insane:
1. To take a job in which the fit is not qutie right on the assumption that I can use it get a position that does fit. (There is also the possibility that I will love the position once I get there.)
2. To hold out for a job that is a good fit, even if it means staying in my current position/extending the job search another year.
Either of these is completely nuts in an academic search, but what about prep schools?
Good luck, us.