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Playing Teacher

Playing Teacher

Written by: Matthew Cade Rob Monahan and Jeannine Brugge
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🎙️ 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.

© 2026 Playing Teacher
Philosophy Social Sciences
Episodes
  • Episode 29: Caps, Gowns, and Grown-Up Drama: Graduation Behind the Curtain
    Jun 6 2026

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    Graduation is supposed to be about the students—but anyone who has worked in a school knows the ceremony often comes with a backstage show of adult politics, bruised egos, seating drama, award rivalries, and exhausted teachers trying to hold it all together.

    In this episode, Matthew, Brugge, and Doc celebrate Dr. Robert Monahan officially earning his PhD in Education before diving into the strange world of school graduations: kindergarten milestones, sixth-grade sendoffs, stage seating power plays, graduation practice chaos, Teacher of the Year tension, and the emotional moments that somehow survive all the nonsense.

    From Doc walking his son to kindergarten a week after a heart attack, to Matthew reflecting on Dylan’s school experience, to Brugge calling out the politics hiding behind the pomp, this episode is funny, reflective, and painfully familiar for anyone who has ever survived graduation season in a school.

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    1 hr and 3 mins
  • Episode 28: The Best Bagel in Town: A talk with veteran teacher, Michelle Henriquez.
    Jun 4 2026

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    In Episode 28, we catch up with Ms. Henriquez, though longtime listeners will understand why she will forever be known to us as Slagle — which, yes, rhymes with Bagel.

    The episode begins with a 20-year-old grudge involving Rob, Matt, and the mysterious school-wide fly infestation that reached its horrifying peak when Slagle discovered a fly floating in her cup of tea. From there, we investigate the truly important matters: her secret brownie recipe, who made the legendary “day-brightening” brownie list, and why some friendships survive only because baked goods are involved.

    But beneath the laughs, this episode turns into a heartfelt conversation about what it really takes to survive and thrive in education. Brugge reflects on the importance of honest relationships with colleagues, especially in a profession that can test even the strongest people. Slagle shares what she has learned from years in the classroom, including the challenges of difficult classes, the power of strong work relationships, and the deep commitment required to support students in an ICT setting.

    Slagle is one of the good ones: a veteran educator, a trusted colleague, a dedicated teacher, a loyal friend, and forever our favorite Bagel.

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    59 mins
  • Episode 27: The Hidden Job Description: School Safety, Student Chaos, and Teacher Survival
    Jun 4 2026

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    In this episode, Matt, Rob, and Brugge pull back the curtain on one of the least-discussed realities of working in schools: teachers are not only instructors, they are also emergency managers, crowd-control specialists, traffic directors, social workers, field-trip logisticians, and sometimes the last line of defense between students and danger.

    Using a recent Oklahoma school shooting incident as a serious entry point, the conversation moves through the lived realities of school safety: lockdowns, shelter-in-place drills, fire drills, evacuation protocols, dismissal chaos, field-trip transportation, custody complications, and the impossible split-second decisions educators are expected to make under pressure. What makes the episode especially compelling is the contrast between formal safety protocols and the messy, human, unpredictable reality of school life. The hosts show how much of teaching happens outside the lesson plan: blocking traffic during fire drills, remembering which adult can legally pick up which child, managing 30 students on a subway platform, and trying to stay calm when the stakes are very real.

    The episode is serious, funny, reflective, and deeply teacher-centered. It captures the emotional labor, physical demands, absurdity, and courage embedded in everyday school work—before ending, naturally, with wrestling names, old school stories, and plans for a future guest.

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    57 mins
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