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When reviewing literature on the 21st century learning aims of secondary school education, there is an emphasis on both digital technology (Beetham & Sharpe, 2013; Bellanca & Brandt, 2010; Partnership for 21st Century Skills, 2014; Trilling & Fadel, 2012) and autonomy or acquiring social and soft skills (Di Fabio, 2014; Dumont & Istance, 2010; Finegold & Notabartolo, 2010; Wagner, 2008). This paper explores the hypothesis that there is some level of incompatibility between education for digital literacy and education that aims to support the attainment of the fundamental soft skills necessary for autonomy. My hypothesis is explored through a case study of a three-day conference I attended called the NEXTschool summer institute. It was organized around considering what a high school of the future could ideally look like in the Canadian context, in Quebec. The institute included presentations made by academic scholars, coupled with focus group conversations featuring a diverse group of teachers and administrators from the province. One of the objectives of the NEXTschool summer institute—and the one that drives the focus of this case study—was to figure out how to engage students in 21st century learning, whatever that may have meant to the various educators participating in the institute. Through putting the ideas of educators from the institute into dialogue with literature on 21st century learning, this paper explores the barriers posed by digital tools in productive ways, leading to strategies that can support educators trying to balance students’ self-reliance and their critical digital literacy.