This essay seeks to contribute to growing discussion concerning the need for more intentional inclusion of habits of mind in curriculum development, particularly in undergraduate general education, and to fuel an examination of the "dialectical" relationship between skills development and the development of habits of mind. The essay begins by generating a tentative curriculum map for the development of a set of habits of mind. It then provides an overview of the theoretical framework of dialectical analysis, which is used to identify points of synergy between skills development and the development of habits of mind. This essay hopes to enrich and expand the ways we think about undergraduate general education and spiral curriculum design, with the ultimate goal of illuminating the role of undergraduate pedagogy in shaping the academic habits of mind and professional character that we wish our students to develop. Toward that end, this essay encourages us to recognize that our students don't magically transform from one state to another but instead undergo a gradual stepwise evolution, and to commit ourselves to better understanding precisely how that evolution occurs by examining the dialectical relationship between skills development and the development of habits of mind within our courses and curricula.