College campuses have experienced a recent resurgence of student activism, particularly in response to some of President Donald Trump's executive orders as well as controversial speakers like Ann Coulter and Milo Yiannopoulous. Student activism presents both challenges and opportunities for higher education leaders seeking to engage productively in these often complex and highly charged issues. We conducted a phenomenological study of ten student activists and eight administrators at three universities to examine the meaning and goals they identify in their experience of campus activism. Findings indicated students identify their activist involvement as highly meaningful, especially with regard to what they feel they learn in college. Similarly, findings indicated administrators found their experience with student activists to be highly consequential in terms of both career satisfaction and dissatisfaction. We also found communication differences between student activists and administrators, even on topics where they generally agree. Given the frequently high stakes nature of contemporary student activism, we present recommendations for practice in the context of understanding these communication differences.