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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 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 career
• Veteran teacher archetypes and end-of-career shifts
• Confidence, burnout, and finding a second wind
• Curriculum drift: stable lessons vs constant change
• Teaching as performance, engagement, and iteration
• Retirement mindset, identity, and adaptability

If you’ve ever wondered how teaching changes after 15, 20, or 30+ years in the system—this one hits home.

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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 ever worked in a school, acted on a stage, or simply had “one of those days,” this episode will feel like home.

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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 “Grandpa Sneezes Trains” and “Wing It”
• Bird encounters and the mysterious NYC pigeon curse
• Writing and acting on subway rides
• Fried watermelon and fair food adventures
• Teacher burnout, SEL, and life balance

What starts as a talk about teacher parking nightmares turns into an honest, funny, and heartfelt look at the teacher experience — where humor, exhaustion, and creativity all collide.

Would you risk a ticket for a good parking spot? Tell us in the comments

Featuring: Rob, Matt, and Brugge

Topics: NYC teacher commutes, alternate-side parking, creative classroom life, and the art of laughing through chaos.

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