In this chapter, I begin by considering Poet A – Kierkegaard’s compelling pseudonym who embodies how we usually understand and respond to this mood state. Poet A’s account reveals three key facets of boredom: the incessant striving of our voracious ego, the onset of existential fatigue, and our ever-resilient attempts to fend off boredom, seeking both to maximize freedom and maintain control. I then turn to Kierkegaard’s analysis in Sickness unto Death, penned by the pseudonym Anti-Climacus. Rather than understanding boredom as a neutral mood state that comes and goes, Anti-Climacus diagnoses it as laced with forms of despair that easily overtake us. When we maneuver to escape this kind of boredom, we only become further mired in it. Anti-Climacus’ framework illuminates and brings conceptual depth and insight to the two dominant boredom responses I noted in the introduction, avoidance and resignation.