We are all very familiar with the conceptual “rule of three” as in bad things come in threes and the third time’s a charm. But did you also know that there are numerous psychological, philosophical, and rhetorical references to the “rule of threerule of three” that purport that things are more engaging, more dramatic, and more effective when grouped in thirds? The Biblical Holy Trinity; Aristotle’s time, place, and action; the three dramatic conflicts—internal, relational, and external; the Three Musketeers; MLK’s “free at last, free at last, free at last”; and the three-act structure—beginning, middle, and end—just to name a few. We, the three authors, colleagues, and friends, shamelessly borrow from the wisdom of the triad, Kim, Laura, and Terri, as we lay out our stories and construct a compelling account of the challenges, truths, and lessons of teaching and leading in a traditional high school today. As you can imagine, our journey thus far feels a bit like a boxing match; lots of bobbing and weaving, ducking, and swinging, winning several rounds and losing a few. What follows is our enlightened albeit cautionary tale.