In this talk, members of the 2022-2023 Praxis Program cohort (Malcolm Cammeron, Caroline Carter, Winnie E. Pérez Martínez, and Samantha Stephens) and Brandon Walsh discuss their recent publication in the Journal of Interactive Technology and Pedagogy entitled “A Way In: Digital Pedagogy Training with Low-tech, Speculative Workshops.” Students new to digital humanities often feel pressure to attain a degree of expertise before they can meaningfully contribute to the field. This anxiety poses significant challenges to efforts to provide training in digital pedagogy, as students often feel unequipped to engage in teaching conversations while still struggling to gain their footing with the underlying technologies. We argue that speculative pedagogical assignments can introduce students to digital pedagogy even as they develop their own relationship to the technologies they aim to teach. After sharing the theoretical and practical framing for the exercise, we share case studies drawn from its implementation in the Praxis Program in Digital Humanities at the University of Virginia Library’s Scholars’ Lab.