We've touched on this issue in the past, but it's worth revisiting in light of this e-mail from a job seeker:
I'm on the job market (not for the first time) and I worry I'll be perceived as "stale". From what I hear, lots of philosophers think it looks very bad that, after a few years out of a Ph.D. program, there's no tenure-track position on my CV. I have a few questions that I hope you or your readers might be able to answer: i. Do people have a sense of how much "staleness" continues to matter even for candidates who are in other ways attractive -- some good publications, lots of teaching experience? ii. If you continue to publish (or publish decent stuff) does that make you any less "stale", or are you still considered obsolete or defective simply in virtue of your defence date? iii. Is "staleness" less of an issue these days than in the recent past, in light of the terrible job markets and overall economy since 2008? iv. Do people have any tips about what a "stale" candidate might do to compensate?
The "staleness" issue, as I think about it, is this: the more years since the PhD that the candidate does not have a tenure-track job, the more likely hiring departments are to draw negative inferences from that fact. Prior to the economic collapse, my sense was that staleness worries kicked in after 4 or 5 years; I would hope that hiring departments are allowing that strong candidates may take considerably longer these days to find a tenure-track position. As to the other questions, I'll make just one comment now, and open comments for thoughts for readers; my one comment is that the longer out from the PhD you are, the better it would be if one or more of your letter writers might speak to that and make clear why this does not support any negative inferences about your candidacy. Signed comments preferred, but job seekers may post anonymously.