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360. Why I’m Not Proud

Posted on November 19, 2025November 18, 2025 by caritagardiner
Screenshot 2025-06-08 at 7.26.19 AM

The photo above shows me giving a speech the night before last spring's graduation. If you want to watch the speech, you can click this link and advance about 27 minutes. I am proud of my speech and was thrilled with how the 2025s reacted to hearing my words.

You might be thinking, "The title of this post is 'Why I'm Not Proud,' but she wrote that she is proud. What's wrong with this woman?" I hear you, but "Why I'm Not Proud of Them" as a title didn't have the vibe I wanted.

Let's be clear: I'm thrilled for the 168 2025s who graduated from Hotchkiss last May. Equally, I will be delighted for however many 2027s have to listen to me give another speech in a year and a half (June 3, 2027, if you're marking your calendar). BUT I won't be proud of the students because "proud" implies that it's my doing, and I can't take credit.

I try to help the kids I dean and teach and know to make smart choices and accomplish their goals, but I know that how they spend their time will be, ultimately, their decisions to make. I can't take credit for their successes, just as I won't own the blame when they fall short.

Last year, the 2025 Senior Prank Day went sideways. While some parts of the prank (moving the chairs to the center of the dining hall and surrounding them with tables and "Warning" tape–carried out with the blessing of the head of dining) seemed pretty funny to me (humorous enough that I got up early to help them). On the other hand, some other aspects of the chaos the kids created caused fire hazards and dangerous situations throughout the Main Building. I was in my office while Seniors were moving items, but I didn't know what they were doing, nor did I participate. Would it have been possible for me to monitor 168 kids who were spread out in a 25,000 square-foot building? I don't think so.  But even if I could have seen everyone everywhere all at once, I wasn't doing the acts. The kids didn't do the pranks I told them in advance not to do (ones that were cruel to individuals), but they did go off-script in adding new forms of disarray, some of which were bad. All this to say, I wasn't the one perpetrating anything, and I don't take responsibility for what other people did.

At the same time, I also don't deserve accolades for all of the great things they accomplished in their three years with me as their dean. I was happy for them when they did well in their classes, sports, theater, debate, clubs, etc, but I can't take credit for those successes unless I also want to take the blame for when they cut class, failed tests, didn't complete homework, gossiped, etc.

I'm not a fan of literal rollercoasters, but working with teenagers is a ride I enjoy. I'm not proud when they do well or ashamed when they fall short, but I'm here for all of it. I support them and hang around to pick up the pieces when they need bolstering, to clap when they deserve applause, and to offer my thoughts when they need a redirect. What do you think? Please share your responses 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

Read my recent “Why” Wednesday Blog Posts

  • 362. Why Have a Motto
  • NetGalley Review of An Academic Affair
  • NetGalley Review of Hate You, Maybe
  • 361. Why Life’s Going to Life
  • NetGalley Review of Something Wicked
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