PhD planning graduates face an increasingly competitive academic job market. In this commentary, seven recent graduates provide qualitative descriptions of the complicated and ever-changing expectations graduates face. We situate this within a larger reflection on the neoliberal academy that promotes a culture of competitiveness over care and production over purpose. We emphasize how this system is seemingly antithetical to the transformative planning work needed to address the most pressing planning issues of our time and provide suggestions for meeting shifting expectations, evolving training and support needs, and opportunities for a more compassionate tenure-track market. Our commentary has implications for doctoral pedagogy, the tenure-track market, and the academy.