Experiential teaching practices can provide transformative learning opportunities for students. However, thus far the experiential education literature considers "experiential activities" monolithically, without acknowledging differences in emotions, particularly negative emotions, students may experience or educator skill in facilitating them. We hypothesized and assessed a "step up" taxonomy that differentiates activities by the negative emotions that students may experience and the educator skill required to run the activity effectively. We mapped 18 representative experiential activities onto four different levels, each requiring increased educator facilitation skill in managing potential student emotional distress. We proposed that as levels of student emotional risk and engagement increase, so do required educator disciplinary knowledge and facilitation skill in using different activities. Using survey data, a principal component analysis indicated a four-level taxonomy populated by different teaching activities. After sharing our hypothesized taxonomy and discussing how we modified it after empirical examination, we end the article with avenues for future research and practical considerations for experiential educators in any discipline that integrates experiential activities.