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Playing Teacher
🎙️ What is a teacher, really?
And what’s it actually like inside a New York City school?
Welcome to Playing Teacher, where veteran educators Matt and Rob—with over 40 years of combined experience teaching in NYC—pull back the curtain on the myths, realities, and moments that make education unforgettable (for better or worse). From the mysterious teacher’s lounge to the myth of “summer off,” they explore what really happens when the classroom door closes.
This isn’t a shiny brochure version of school. It’s the real deal:
🧠 Learning vs. schooling.
❤️ What kids actually carry with them.
🔥 How teachers and counselors survive systems built to burn them out.
And when we’re lucky enough to have her, we’re joined by Beanie—school counselor, educator, and recurring co-host—who brings powerful insight, grounded compassion, and the kind of perspective only someone who's worked both inside and around the classroom can offer.
👥 Guests range from teachers, students, and administrators to learning scientists, former kids (yes, really), and other unexpected voices from the world of education.
Whether you're in the classroom, supporting from the sidelines, or just trying to make sense of how we learn and why it matters—this is your hallway pass to the inside.
Playing Teacher
Episode 6: I Did It My Way: Authenticity in a System That Doesn’t Always Want It
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 Whether it’s pushing against outdated norms, teaching in ways that aren’t “in the handbook,” or simply showing up as your full, weird, passionate self, going against the grain can make you stand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.
