If you haven't had enough of the "entering law teaching" discussion, then you may want to check out Eric Goldman's latest series of posts on transitioning from being an experienced attorney to being an assistant professor of law.
Eric may touch on this in later posts, but one strand of conventional wisdom tells would-be applicants that practicing too long can hurt you in the law teaching pool. I have family members (much more credentialled than me) who have seriously considered law teaching, and their mentors told them not to practice more than five years. After five years, the theory goes, the additional experience will hurt an applicant more than help. If you look at assistant professors across the board, many of them will fit the under-five year mold, and some will have practiced only one year after clerkship. I myself practiced exactly five years.
How can this inexperience bias truly exist?
From being on this side of the hiring process, I can tease this out somewhat. I definitely have the sense that at some level, hiring committees want to hear you say that you have always wanted to be a law professor. You figured out in law school that you wanted to be a law professor, and you went and got your feet wet and bided your time. What hiring committees don't want to hear you say is that you thought you wanted to practice and now you're not sure, so you're exploring other options. To many, the teaching profession is not one of many employment options, it is a calling. Therefore, to weed out the many qualified applicants, committees distinguish the seekers from the chosen.
So, the longer you stay in the legal profession, the more you give the impression of trying to figure out what you want to be when you grow up. Or worse -- you may look like a seventh-year associate who has realized you aren't gong to make partner and are now scrambling. If you have practiced an even longer time, you may look like someone who wants to wind down into semi-retirement.
What can someone who is a little long in the lawyer tooth do? Have a story. When asked "Why do you think you would like to teach?," have a plausible story of how you have always thought you wanted to teach, but you have also enjoyed practicing. Describe how you have struggled with the decision, but how you are sure that this is the right time in your life to finally pursue your dream. If this story does not ring true with you, then you may want to reconsider. Teaching and writing are second nature to people who feel called to do it, but may feel like pulling teeth to someone just looking to escape from practice. I may work less hours than I did at Skadden, but I definitely work more hours than a lot of attorneys I know. If you are merely looking for a break on hours, there are many more lucrative options.
On a related note, if asked about your transition, don't focus on the negatives of law practice. Even though everyone in the room will agree with you, no one likes a malcontent. Even a justified malcontent.
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