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One decision can rewrite your entire life: quit the job, take the risk, and figure it out later. That’s the thread running through our conversation with Jim Lanzarotta, a former boss, longtime educator, and the kind of school leader who still gets invited to dinners by students he taught decades ago. We start in Brooklyn, with memories that sound impossible now: walking home for lunch, navigating overcrowded schools, and learning independence the hard way.

From there, Jim takes us through the turns that shaped his teaching career and education leadership style. We talk about health issues, working while still in high school, and the kind of discipline policies that could derail a kid on the edge of graduation. Then it’s college, marriage young, a “safe” insurance job that goes sideways, and a leap into public education that begins without a single education course on his transcript. It’s honest, funny, and full of the messy details people usually edit out.

Once Jim lands in Wyandanch and later West Islip, the conversation opens up into special education, mainstreaming and support services, school culture, and what student success really looks like over time. We also get into his years as an attendance teacher, basically a truancy officer, back when that meant knocking on doors and physically bringing kids back to school. If you care about teaching, school administration, student relationships, and how careers in education actually unfold, this one hits hard.

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Send us Fan Mail

Send us Fan Mail

You can tell a lot about a teacher by the part they leave out and Jesse Fawess doesn’t hide the messy parts. We start with the honest origin story: a Babylon kid pulled toward art, architecture, and surf culture who tries college, bails after three days, comes home, pays rent, and has to figure out what adulthood looks like without a script. Somewhere in that uncertainty, teaching keeps resurfacing, not as a “dream job” slogan, but as the one place he feels naturally good at connecting with kids.

We talk about the real inflection points that shape a teaching career: the child psychology program that puts him with preschoolers, the mentor who basically calls his future, and the community college reset that turns drifting into a plan. From student teaching in Babylon to getting hired in West Islip in 1997, Jesse shares what it felt like to walk into a building, learn the culture fast, and eventually find his stride in sixth grade team teaching. Along the way, we get into what great teams actually do for students and why “legacy” in education is often just years of consistent care.

Then we go wider: classroom technology before it was normal, Macs and iMovie as creative fuel, and why kids now experience tech like furniture, it’s just there. We also get candid about how parenting and expectations have changed, why discipline looks different, and how we try to reach kids without turning everything into punishment. If you care about teaching, classroom management, education trends, or what schools feel like from the inside, you’ll find a lot to argue with and a lot to nod at. Subscribe, share this with a teacher who will have opinions, and leave a review with the biggest change you’ve seen in schools.