With the rise of a global marketplace for research ideas, and the increased precarity of teaching positions, academic labor occurs more so than ever in conditions that resemble those faced by independent workers. The authors came to this realization in the process of bridging these two worlds, so dissimilar institutionally and yet so resonant existentially. The freedom that must be coped with, the personal investment work, and the precariousness experienced, for both independent workers and academics, contribute to an obsession with productivity as a way to manage strong and conflicting emotions attendant to work. This essay offers a lens to interpret that obsession, and some advice for countering it and crafting a viable and vital working life, by cultivating connections to significant people, a specific and evocative place to work, soothing routines, and an overarching purpose. The authors must examine the experience of those who theorize for a living, this essay argues, if they aspire to bring theories to life. Focusing on the personal, existential experience of “being” an academic, the essay complements work on the social and institutional challenges of “doing” academia, and contends that sustaining personal investment in work is essential to developing more pluralistic and potent theories about the contemporary world of work.