Roman rhetorical training had a strange requirement: advocates were regularly assigned to argue positions they personally opposed. Not as a exercise in sophistry, but because Cicero — who systematized this practice — believed that genuine competence in any domain meant being able to inhabit the strongest version of your opponent's case. He called it *in utramque partem*, arguing both sides, and it was considered a precondition for serious counsel, not a debating trick. The career implication is underappreciated. Most professionals develop their expertise by accumulating confirmations — projects where their approach worked, managers who validated their instincts, teams that moved in their preferred direction. The result is fluency in one dialect of the work, plus a quiet inability to diagnose why people who think differently keep succeeding. What Cicero's training demanded was periodic deliberate exile from your own viewpoint. Not devil's advocacy for its own sake, but the disciplined construction of the best case against your current direction — your choice of role, your working style, the career logic you've been operating from. The moment you can argue that case persuasively, you've located something worth examining. And occasionally, you'll find yourself more convinced by it than you expected.

What is the most compelling argument that your current career trajectory is the wrong one — and have you ever actually constructed it, in full?

Drawing from Roman Rhetoric / Ciceronian Dialectic — Marcus Tullius Cicero