Playing Teacher

26 Episodes
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By: 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 sy...

Epsiode 26: From the Classroom to the Central Office: A Conversation with Dr. Neill Alleva
#26
Today at 6:00 PM

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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. 


Episode 25: Stats, Laughs, and Staff Bathroom Scandals
#25
Last Sunday at 11:00 PM

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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 firs...


Episode 24: Desk Jockeys: The Hidden Politics of Classroom Furniture
#24
03/26/2026

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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...


Episode 23: AI in the Classroom: Tool, Threat, or Teacher?
03/06/2026

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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...


Episode 22: The Aging Educator: Sweet Spots, Second Winds, and the Retirement Countdown
#22
01/15/2026

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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...


Episode 21: Body Odor, Bad Falls & Behind-the-Scenes Book Building
#21
11/21/2025

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Tech trouble, Mario cosplay, workplace mishaps, and way too many stories about falling down.
 

In this episode, Robert, Matthew, and Brugge dive into a chaotic mix of muted microphones, Halloween go-kart adventures, deodorant disasters, acting auditions, and the everyday physical hazards of working in schools. From stepping in dog poop to tripping in crowded hallways, the team shares honest (and hilarious) stories from classrooms, childhood, and beyond.

They also dig into their ongoing creative projects—including book design, AI-generated descriptions, and gathering early reviewers. If you've eve...


Episode 20: Teachers vs. NYC Parking: The Ultimate Urban Survival Story
#20
10/21/2025

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Every NYC teacher has a horror story — but this one starts with a parking meter.

In this episode, Matthew, Brugge, and Robert tackle the ultimate urban educator struggle: finding a parking spot in New York City. From 4:30 AM commutes to warehouse parking hacks, $200 lots, and alternate-side madness, the trio shares hilarious, relatable stories about how teachers navigate one of the most stressful parts of their day — getting to work.

Along the way, the conversation takes some wild detours (in true teacher fashion):

AI-illustrated children’s books like <...


Episode 19: Teachers, Titles, Telehealth, and Trust
#19
10/17/2025

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Overview

In this milestone episode, the hosts celebrate reaching 500 podcast downloads and reflect on personal experiences that reveal how trust, credentials, and communication shape everyday life — from healthcare visits to professional identity. The discussion balances humor and insight as they explore the quirks of the healthcare system, telehealth mishaps, and the nuanced meaning of titles like “Doctor” in both education and medicine.

Healthcare Experiences & Telehealth Confusion

Matthew opened up about a recent telehealth appointment that turned unexpectedly chaotic — he was dire...


Episode 18: Fortnight to Fortnite (Culture as Curriculum)
#18
10/02/2025

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A glitchy start becomes a candid systems-level conversation about age dynamics and professional identity across schools and clinics. After wrangling audio issues, the team unpacks how age and experience shape credibility, communication, and decision-making—from first-year teachers to veteran administrators, from protocol-driven residents to diagnostically agile physicians. They trace the “hidden curriculum” that governs status signals, masking, and code-switching at work, then examine how cultural references (from Fortnite to K-dramas) succeed—or fail—as pedagogical bridges. Along the way, Robert reflects on mimicking admired mentors as a deliberate practice for skill acquisition, and everyone w...


Episode 17: Teachers on the Move: Diets, Fitness, and Fresh Starts
#17
08/31/2025

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In this episode, Matt, Rob, and Brugge share candid reflections on the challenges of maintaining health and balance as educators. The conversation spans from their high school experiences to their ongoing efforts with weight loss, diet programs, and creative fitness routines, whether it’s sprinting empty hallways, dusting off a pogo stick, or sticking to intermittent fasting. Along the way, they reminisce about potluck traditions, school gym memories, and the temptation of diner pancakes and mocha lattes. With Brugge preparing for a new school, and Matt and Rob revisiting past projects li...


Episode 16: Behind the Curtain: How Teachers Really Get Hired in New York City
#16
08/18/2025

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Getting hired in the New York City Department of Education (NYCDOE) isn’t just about what you know—it’s often about who you know. In this episode of Playing Teacher: The Podcast, we pull back the curtain on the hiring process in the largest school system in the country. From the nerve-wracking interviews to the networking that makes a difference, we explore the good, the bad, and the ugly of how teachers land jobs in the NYCDOE. Whether you’re an aspiring educator or a veteran looking to understand the system better, this can...


Episode 15: Why We Left Teaching (and Where We Hid While We Stayed)
#15
07/03/2025

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In this episode of Playing Teacher, Robert, Matthew, and Brugge dive deep into the bittersweet—and sometimes hilarious—world of teachers leaving their jobs and the hidden realities behind the classroom door.

They talk about:

The emotional chaos of packing up years of teaching memories into giant bagsThe secret hideouts teachers swear by to survive the school day (side lab supremacy, anyone?)Epic hide-and-seek strategies for teachers and kids alikeProfessional development’s most uncomfortable moments—including yoga sessions gone very wrongRecession Santa horrors and gifts no one wanted


It’...


Episode 14: Field Trip Fails, Emergency Room Runs, and Outback Steakhouse
#14
06/22/2025

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In this unforgettable episode of Playing Teacher, Rob, Brugge, and Matthew take us behind the scenes of one of the most chaotic rituals in education: the school field trip.

It all begins with a subway disaster—Matthew describes watching a class trip unravel on public transit, complete with unsupervised elementary students and overwhelmed teachers. That story kicks off a deep (and hilarious) dive into the real logistics, emotional toll, and occasional absurdity of planning field trips as educators.

Brugge brings the heat with a list of...


Episode 13: The Secret Game of Calling Out...Rules, Risks & Ridiculousness
#13
06/08/2025

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In Episode 13 of Playing Teacher, we pull back the curtain on one of the most absurd realities of working in education: calling out sick. From planning sub folders while mid-fever to writing emergency plans in a NyQuil haze, we explore the ridiculous, guilt-ridden, and occasionally hilarious world of teacher absences.

We talk about:

The unspoken Olympics-level effort required just to stay homeWhy "mental health day" is code for “I’ve snapped but still care enough to write 6 pages of sub plans”The emotional toll of guilt vs. the physic...


Episode 12: Teacher Headlines, DOE Dreams & The 50-Minute Flop
#12
05/31/2025

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📘 Episode Description:

In this episode of the Playing Teacher Podcast, we debut a brand-new segment: 🎤 Teacher Headlines with Janine Brugge, where we explore what’s really going on in the world of education—both the serious and the absurd.

This week, we take a hard look at the NYC Department of Education’s failed initiative known as “Inquiry” or the “50-minute” plan—an attempt to create time for professional development and student support that went sideways due to a critical failure: n...


Episode 11: Field Day, Minecraft Battle & Upstanders
#11
05/23/2025

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In this episode of the Playing Teacher Podcast, we delve into the vibrant world of education, sharing personal anecdotes and professional insights that resonate with educators, students, and lifelong learners alike.

🎯 Episode Highlights:

Field Day Reflections: We reminisce about their own Field Day experiences, discussing the joys and challenges of organizing such events, and the lasting impact they have on students.Minecraft in Education: Explore how Brugge's team navigated a citywide Minecraft competition, emphasizing the importance of collaboration, creativity, and resilience in educational gaming env...


Episode 10: Pacing, Pop Culture, and the 30-Second Reprimand
#10
05/15/2025

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🎙️ Playing Teacher Ep. 10 – Pacing, Pop Culture, and the 30-Second Reprimand

Description:

In this episode of Playing Teacher, Matt recounts a jaw-dropping moment when he was called out in front of students for returning to class 30 seconds late after using the bathroom—yes, 30 seconds. Jeannine and Robert reflect on how often teachers are denied even the most basic human grace. This leads into a dynamic, often hilarious discussion on classroom pacing, student rapport, and when to stick to the script—or throw it out.

💡 Robe...


Episode 9: Carrots, Sticks, and the Art of Motivation in the Classroom
#9
05/12/2025

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In this episode of Playing Teacher, we unpack one of the most familiar — and controversial — strategies in elementary education: rewards and incentives. From treasure boxes and pizza parties to Dojo points and public praise, we examine how these practices shape student motivation, behavior, and identity in the classroom. Are we inspiring effort — or cultivating compliance? Are extrinsic rewards helpful stepping stones or long-term obstacles to deeper learning and self-regulation?

Whether you're a teacher filling sticker charts or a parent wondering about prize-based learning, this episode offers practical insights and philosophical food fo...


Episode 7: Remember When… (Memorable Moments & Movie Magic)
#7
04/12/2025

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In this episode of Playing Teacher, we talk about the moments that stick—the scenes from our lives as educators that play in our minds like movies. You know the ones: the hallway showdown, the field trip fiasco, the spontaneous dance party, the kid who said something so profound you wrote it on a post-it and never threw it away.

We reflect on how these memorable teaching moments—big or small, funny or moving—aren’t just one-off stories. They’re what give the work meaning. And much like scenes from iconic fil...


Episode 8: Teaching and Learning During COVID in NYC
#8
04/10/2025

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In this episode of Playing Teacher, we rewind to one of the most surreal, exhausting, and defining chapters in modern education: COVID in New York City. Teaching during the pandemic wasn’t just about pivoting to Zoom—it was about surviving, adapting, and finding humanity in the chaos.

We talk candidly about what it meant to be an educator when the world shut down: the scrambled emails, the lost students, the tech failures, the eerie silence of empty classrooms. But we also talk about the grit, the creativity, and...


Episode 6: I Did It My Way: Authenticity in a System That Doesn’t Always Want It
#6
04/10/2025

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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...


Episode 5: Are We Okay? (Spoiler: Probably Not)
#5
04/09/2025

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Teaching, Sanity, and the Fine Line Between Passion and Burnout

In this episode of Playing Teacher, we ask the question that lingers behind every empty coffee cup, every hallway meltdown, and every wildly creative bulletin board at 2AM: Are we okay?

Spoiler alert: probably not.

We take a lighthearted but honest look at the emotional rollercoaster that is life in the classroom. We talk about the toll teaching can take on your mental health—not in a clinical, diagnostic way, but in the way teachers ac...


Episode 4: Roll Film: Cinema, Memory, and Metaphor in the Classroom
#4
04/09/2025

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In this episode of Playing Teacher, we pull back the curtain on a not-so-secret weapon in our teaching toolbox: cinema. Whether we were screening something in our makeshift movie theater during lunch or showing a film to an entire class, movies weren’t just a break—they were world-builders.

But this episode isn’t about the obvious curriculum tie-ins (you won’t hear us talking about “let’s watch October Sky during the space unit”). Instead, we explore how film can plant vivid experiences in kids’ minds—scenes, emotions, and stories that b...


Episode 3: The Hook: The Art of Captivation
#3
04/09/2025

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In this episode of Playing Teacher, we dive into The Hook—that elusive, electric moment when a teacher pulls students in and makes them want to learn. It’s the magic trick, the spark, the wink across the room that says, “This is going to be good.” But here’s the thing: it’s not in the lesson plan template, and it sure doesn’t show up on most rubrics.

Too often dismissed as fluff or misunderstood by administrators and even some teachers, The Hook is actually one of the most powerful tools...


Episode 2: Preps and Lunches (and Superpong)
#2
04/09/2025

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In this episode of Playing Teacher, Matt, Rob, and Brugge crack open one of the most sacred and underrated parts of the school day: preps and lunches. More than just breaks, these windows of time were life-saving lifelines in the relentless hustle of NYC public school teaching. We reflect on how these moments offered space to breathe, plan, decompress—or just stare into the void with a slice of pizza in hand.

But it wasn’t all quiet recovery. Sometimes, it was survival through play. Enter Superpong—a game...


Episode 1: The "Expert" Teacher
#1
09/06/2024

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“Ok, if it’s so easy you teach my class..please show me the way.”  Ah, the fantasy of every teacher. Imagine a scenario where you’re told to change roles and write up your supervisor who wants to show you how it’s done…you know because they were once an “expert teacher.” But what if it bombs? Matt and Rob relive this once in a teacher’s lifetime experiment and discuss better alternatives to how teachers are evaluated.  More importantly, who is qualified to make these evaluations?

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