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343. Why Name Your Whys

Posted on July 23, 2025July 22, 2025 by caritagardiner
Screenshot 2025-02-16 at 9.11.11 AM

I have an advisee with whom I meet every week. At some point I noticed that we had roughly the same conversation every time she came to my office:

Me: How are things going?

Her: Not great. I have a paper that's late and a test I'm not ready for and I wasted all of yesterday scrolling on my phone.

Me: What can you get done today?

Her: I can do the late homework for my other class and ask for an extension on the paper.

Me: How are you feeling about things?

Her: Horrible.

Me: What's getting in the way of your feeling good about my work?

Her: My phone. I think I'm addicted to it.

Me: Want to leave your phone here?

Her: No.

Etc. Every week, same same same. At some point, we both got tired of having versions of this conversation. She knows that in the moment, she makes decisions that she later regrets, but she can't stop choosing those same paths over and over. And in this way, she spent much of her time feeling bad about homework, about her courses, about herself.

Same questions, same answers, same behavior. We covered the same ground so many weeks, but since I'm supposed to advise, at some point, I had the idea to ask her different questions. Instead of seeking to find out what was due and what was overdue, I decided to ask her about why she wanted to do well in school. I asked why she liked being in the clubs she was in and doing the sports she did. When people don't have a why, everything feels like grinding. When people know their why(s), they can accomplish more difficult tasks with less anguish. Working hard FOR something is much easier than working hard without cause.

I have lots of whys that make pushing myself every day part of who I am rather than any externally imposed tasks ever could. Here are some examples:

  • I want to be around and healthy to see the royalty pictured above well into their middle-aged lives, so it's not a burden for me to work out every day.
  • I want to be able to enjoy a long retirement with my husband in Maine, so it doesn't bother me to save a chunk of each paycheck now.
  • I would love to see my name on the cover of a book at a bookstore, so I can make time every day to write.
  • I want to be a resource for the kids I dean, so I keep my office stocked with candy and try to listen to what they need from me.

Those are my top four, but if you want to read 342 of my other why's, you can scroll back through my posts. What are some of the big whys in your life? How does thinking about them help you do hard things? Want to write one of them for a guest blog post sometime? 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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Read my recent “Why” Wednesday Blog Posts

  • NetGalley Review of First and Forever
  • 384. Why The Imperfectionist
  • NetGalley Review of Burnout Summer
  • NetGally Review of How to Find a Guy in Five Weddings
  • 383. Why AI
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