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348. Why Un-Fresh Start

Posted on August 27, 2025August 26, 2025 by caritagardiner
Screenshot 2025-03-23 at 7.54.23 AM

For people in the real world, January first is the beginning of the year, but for those of us in academia, the transition from August to September always marks a beginning. This fall, my twenty-seventh at Hotchkiss, I am taking over as the Dean of the Class of 2027. I like the parallel numbers, but when I contemplate what the alignment of 27's means, I think about the fact that I've had a LOT of new years here. Every school year offers a chance to improve–my pedagogy, my coaching, my interactions with kiddos and colleagues. At the same time, I don't lose the experience I've gained (except when my lousy memory kicks in), so even when the students are different, I'm not coming at everything fresh every time.

As I begin my term as dean for another graduation year's students, I have to remember that I'm not coming at this without experience that will help me navigate rough moments. I might not know all of the students in the grade yet, but I do understand a range of issues. I get how to soften what feels terrible and amplify what counts as success.

While "having a fresh start" might sound like a good thing to some, to me it sounds scary. Instead, I'm choosing to consider this year an un-fresh start–but that doesn't sound great either. Maybe I'll take a running start or a head start. What do you think? Please share your suggestions in the comments.

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WHAT I DO

I serve as a class dean and teach English to high schoolers at a boarding school in Connecticut. I’ve earned a Bachelor of Arts (Amherst College), an Education Master in Learning and Teaching (Harvard University Graduate School of Education), a Master of Arts in English (Bread Loaf School of English), and most recently a Master of Fine Arts in Creative Writing with a certificate in the online teaching of writing (Southern New Hampshire University).

As a writer, I hope to capture the complexity and joy of life in the New England boarding school world. On this site, I share what I know about trying to write fiction while deaning, teaching English, coaching, and doing the other tasks associated with helping to raise over six hundred other people’s children.

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  • cgardine@hotchkiss.org

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  • 383. Why AI
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