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401. Why Start Over

Posted on September 2, 2026September 1, 2026 by caritagardiner
Screenshot 2026-02-08 at 11.00.11 AM

I'm lucky to be starting my twenty-eighth year working in the beautiful, selective school behind this gate. Each new year brings new opportunities and challenges, and I'm here for both the highs and the lows of trying to help teenagers grow up to be the best possible versions of themselves. It's a very cyclical life.

During this year ahead, I will shepherd the Senior class to graduation, but for this post, I've been thinking not about the end of kids' journeys through this place but about how they begin. I know from talking to people in the Office of Admission that when asked, "Why Hotchkiss?" or "Why boarding school?", many of the eager applicants talk about the diversity of the student body and the amazing resources the school offers for students to try new things.

Then, those same students usually continue activities at which they already excel and hang out with people who come from the same places as they do, speak their same native tongues, and share their same world views. If a person isn't going to stretch himself/herself/themselves in novel ways, why bother with the many hassles and expenses of going to school far from home?

Students, I'm speaking to you right now, START OVER. It's not too late to join a totally new club, find new friends, or try out for a new sport. (Diving, anyone?) There are certainly advantages to staying within comfortable bounds, but by taking the trodden path, you're sacrificing limitless opportunities. You don't know yet what you love, what you could be good at, or who could be your people, and if you don't risk the search, you never will.

What new things are you going to try? Which new people are you going to invite to your table? How can you push yourself beyond what's easy and familiar this year? And, while I'm at it, how should I? Please share goals and 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.

WHAT I CAN DO FOR YOU

Teach                    Tutor

Revise                   Edit

Entertain             Enlighten

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Contact Me

  • cgardine@hotchkiss.org

Read my recent “Why” Wednesday Blog Posts

  • 401. Why Start Over
  • 400. Why Conventions of Composition
  • NetGalley Review of The Oxford Guide to Scandal and Lies
  • 399. Why My Presence Shouldn’t Matter
  • NetGalley Review of I Kissed Her First
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