Playing Teacher

Matthew Cade, Rob Monahan, and Jeannine Brugge

🎙️ 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.

  1. Jun 6

    Episode 29: Caps, Gowns, and Grown-Up Drama: Graduation Behind the Curtain

    Send us Fan Mail 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. Support the show

    1h 3m

  2. Jun 4

    Episode 28: The Best Bagel in Town: A talk with veteran teacher, Michelle Henriquez.

    Send us Fan Mail 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. Support the show

    59 min

  3. Jun 4

    Episode 27: The Hidden Job Description: School Safety, Student Chaos, and Teacher Survival

    Send us Fan Mail 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. Support the show

    57 min

  4. Apr 2

    Epsiode 26: From the Classroom to the Central Office: A Conversation with Dr. Neill Alleva

    Send us Fan Mail In this episode, the Playing Teacher team sits down with Dr. Neil for a wide-ranging conversation about education, leadership, and the relationships that shape a career in schools. The discussion moves from the early days of teaching and school culture to PBIS implementation, staff hiring, school leadership, and the realities of guiding a school community through difficult moments, including the COVID era. Along the way, the group reflects on mentorship, memorable colleagues, professional growth, and the kind of human-centered leadership that leaves a lasting mark on students, teachers, and entire school systems.  Support the show

    1h 3m

  5. Mar 29

    Episode 25: Stats, Laughs, and Staff Bathroom Scandals

    Send us Fan Mail In this milestone 25th episode of Playin’ Teacher, the crew looks back at the podcast’s growth, biggest episodes, and where listeners are tuning in from around the world. What starts as a stats check quickly turns into something bigger: a reflection on how the show has evolved from a more traditional education podcast into something looser, funnier, and a lot more rooted in friendship, storytelling, and shared teacher chaos. The team talks Season 2 plans, debates whether the show now belongs in comedy, society and culture, or education, and announces their first guest for the new season: Dr. Neil. Along the way, there’s discussion of standout past episodes, title changes, acting updates, and one unforgettable school story that closes the episode in truly unhinged fashion. If you’ve been here since the early episodes or you’re just jumping in, this is a perfect snapshot of what Playin’ Teacher has become: part teacher talk, part life update, part comedy spiral. Support the show

    59 min

  6. Mar 26

    Episode 24: Desk Jockeys: The Hidden Politics of Classroom Furniture

    Send us Fan Mail In Episode 24 of Season 1, the Playing Teacher team explores the surprisingly loaded topic of desks in schools. From bizarre desk drawer discoveries to classroom desk placement strategies, the conversation moves from humorous teacher stories to serious questions about school resources, furniture inequities, and how physical space shapes instruction. The team discusses how different educators use their desks, why some teachers avoid sitting at them, and how classroom layout affects observation, management, and student relationships. They also reflect on underused school equipment, storage-room mysteries, and the broader resource gap between classroom teachers and administrators. What seems like a simple conversation about desks becomes a revealing look at school culture, teacher identity, and the politics of space in education. The episode also serves as a natural checkpoint as the team nears the end of Season 1 and starts thinking ahead to Season 2. Support the show

    48 min

  7. Mar 6

    Episode 23: AI in the Classroom: Tool, Threat, or Teacher?

    Send us Fan Mail Episode 23 of Playing Teacher tackles one of the biggest questions in education today: What happens when classrooms become dominated by screens, software, and artificial intelligence? Robert, Matthew, and Brugge discuss the post-COVID explosion of digital learning tools, the unintended consequences of assessment platforms like iReady and IXL, and the growing concern that students are spending more time interacting with software than with teachers. The conversation also dives into AI's rapidly expanding role in education, from writing assignments to personalized tutoring, and asks a critical question: If AI can complete many school tasks instantly, what should students actually be learning? The episode argues that the solution isn't banning technology, but redesigning education around deeper thinking, real-world experiences, and human connection. Support the show

    1h 4m

  8. Jan 15

    Episode 22: The Aging Educator: Sweet Spots, Second Winds, and the Retirement Countdown

    Send us Fan Mail What actually happens in a teacher’s final years in the classroom? In this episode, Matt, Robert, and Jeannine dig into the lived reality of the aging educator—not as a comparison to younger teachers, but as its own unique phase of an education career with its own pressures, patterns, and unexpected strengths. We unpack the idea of the teacher “sweet spot” (and whether it’s defined by years, confidence, freedom, or mastery), the concept of a professional second wind, and what it looks like when veteran educators shift their pace, mindset, and classroom identity as retirement gets closer. Along the way, we explore the archetypes we’ve all seen in schools: the teacher who resists change, the one counting down to retirement, and the one who still brings wisdom and stability to the building—even when everything around them is shifting. We also talk curriculum evolution over time (the lesson bank problem), how experienced teachers keep their best “hooks” while adapting to new standards, and why teaching sometimes resembles entertainment: same show, new audience… every single year. Plus: a quick detour into reality TV game dynamics (Traitors), schools running on fumes when admins are out, and the ongoing question—do educators ever reach a permanent “comfortable routine,” or does the job always demand reinvention? Topics include: The “sweet spot” in a teaching careerVeteran teacher archetypes and end-of-career shiftsConfidence, burnout, and finding a second windCurriculum drift: stable lessons vs constant changeTeaching as performance, engagement, and iterationRetirement mindset, identity, and adaptabilityIf you’ve ever wondered how teaching changes after 15, 20, or 30+ years in the system—this one hits home. Support the show

    50 min
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About

🎙️ 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.

Information

  • Creator
    Matthew Cade, Rob Monahan, and Jeannine Brugge
  • Years Active
    2025 - 2026
  • Episodes
    29
  • Rating
    Explicit
  • Copyright
    © 2026 Playing Teacher
  • Show Website
    Playing Teacher