The notion of competencies has been a familiar feature of educational reform policies for decades. In this essay, Pádraig Hogan begins by highlighting the contrasting notion of capabilities, pioneered by the research of Amartya Sen andMarthaNussbaum. An educational variant of the notion of capabilities then becomes the basis for exploring venturesome environments of learning: environments that are hospitable to the cultivation of such capabilities among students and their teachers. In this exploration Hogan emphasizes disclosing the kinds of relations that constitute such environments. In particular, he identifies four kinds of relations and investigates the interplay among them. In the second part of the essay, Hogan reviews an ongoing research project in Ireland that has been promoting such environments in postprimary education: Teaching and Learning for the 21st Century. Although the project avoids proffering universal claims about ‘‘what works,’’ its rationale and conduct nevertheless call policymakers’ attention to what has worked and to the reasons why.