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April 10, 2025 38 mins

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In this episode of Playing Teacher, we talk about something every educator feels at some point—what it means to be yourself in a school system that often prefers you to color inside the lines. Whether it’s pushing against outdated norms, teaching in ways that aren’t “in the handbook,” or simply showing up as your full, weird, passionate self, going against the grain can make you stand out… and not always in the way people like.

We unpack the moments when being authentic can make you unpopular—with administrators, with coworkers, or with the “system.” And we reflect on the quiet courage it takes to keep showing up as yourself, even when the easier route would be to conform.

From hallway politics to unconventional lesson plans, from dress code subversions to the subtle art of staying out of faculty cliques, we explore how hard—and how vital—it is to do it your way. As Frank Sinatra said, regrets, I’ve had a few… but then again, too few to mention.

This one’s for the teachers who’d rather be real than be liked. Who show up, speak up, and shake things up. And who know that sometimes, doing it your way is the only way to stay sane, stay passionate, and stay in the game.

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