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2011 Makeover Issue

Transformers: Taking his show on the road

Josh Gondelman, 26, quit his job as a preschool teacher in Arlington to pursue a career as a comic and writer in New York. His first step: looking outside the classroom for material.

(Dick Mitchell)
August 21, 2011

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As told to Amy Sutherland

It was a hard decision. I’d been there for four years. I’m still kind of nervous about it.

A big chunk of my act is inspired by the kids. About eight months ago, when I started formulating my plan to leave, I started writing less about teaching. I don’t want to have to be a teacher so I can be a comedian.

I grew up in Stoneham. The whole city [of Boston] is very homey, like where Tremont Street meets Tremont Street. I’m concerned about creating that feeling in a big city. I’m not moving to a place where people are going to come over with a pie and say, “Hi, we’re the Hendersons.”

I feel like in Boston I was a little too complacent. I could get on stage when I wanted. I didn’t feel like I was pushing myself. I could get work in New England and not have to travel too much. I have to give up this level of ease and comfort.

I’m trying to book as much work as I can, enough to keep me solvent through December. And then in December, if there’s no prospect for anything else, I may up the hours at my part-time tutoring gig. If I moved to New York and went back to full-time teaching I would miss opportunities. I can’t go to New York and hope someone is going to see me teaching preschool and hire me to write for a late-night show.

I haven’t made a lot of finite goals. I’m waiting to go down and see what’s possible. If I say I’m getting on David Letterman in a year and I don’t, where am I then?