For the past 15 years, I have moved back and forth across the border between academia and the workplace as a writing teacher, researcher, consultant, trainer, and advisor. Although my full-time position is within a university, I have sought to influence workplace literacy practices and policies by going into the field. This chapter explains some of the difficulties I have faced in my work as a university-based literacy consultant and describes some of the strategies I have used to overcome those difficulties. I believe the difficulties help explain the tensions and misunderstandings that exist between academia and the workplace, and I hope the strategies might be useful to those who seek to change professional literacy practices.