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371. Why Sign Up

Posted on February 4, 2026February 3, 2026 by caritagardiner
Screenshot 2025-08-22 at 8.51.46 AM

Though I don't spend nearly as much time as I'd like at our house in Maine, I do subscribe to several regular email newsletters about what's going on in our town. I know when the Windham Town Council meets, what's going on at the Windham Town Hall, and all of the many events sponsored by Windham Parks and Recreation. Last summer, through one of these emails, I learned about a hike that was co-sponsored by the Appalachian Mountain Club and the Presumpscot Regional Land Trust, both of which are great organizations that help preserve areas in which people can enjoy natural settings.

That first hike was super fun. My husband (Hi, CIO!) and I met some new people and learned about two more educational hikes the AMC was running later in the summer and we found out about a hiking series the PRLT had organized with the Town of Windham. On the first one, we saw an egret nest with egrets in it, and on the second, we learned about the history of the area. For the trail activity, I ended up taking five more hikes on PRLT preserves so that I could fill my stamp booklet (pictured above) to "win" the challenge, for which I could pick up a limited-edition water bottle in the fall. Here's a photo of the bottle:

Screenshot 2026-02-03 at 6.43.12 AM

All of the hikes took me to beautiful trails in preserves I hadn't explored before. I went on some of the hikes with friends and some alone. I walked some, jogged others.

I've been thinking that I should find more hiking trails in Maine for years, but I never acted on that thought. With the little booklet in hand (or in my pocket), I found new sites to explore and had a great time. If I hadn't signed up for the challenge (which I acknowledge was probably designed for kids), I would probably have found reasons not to get out.

Have you ever signed up for something because you knew it was good for you, and having signed up, stuck to it better than you would have just by knowing it was the better path? Please share your stories in the comments. And next time you have the opportunity to sign up for something, take it...and then come back here and share your tale in the comments (or write a whole Why Wednesday post about the experience).

6 thoughts on “371. Why Sign Up”

  1. Jenn says:
    February 4, 2026 at 5:39 pm

    I love everything about this!

    Reply
    1. caritagardiner says:
      February 4, 2026 at 5:52 pm

      Yay, what are you going to sign up for? Or what have you signed up for and recommend?
      Thanks for reading and commenting!

      Reply
  2. Kate says:
    February 4, 2026 at 10:22 pm

    You convinced me to sign up to do a triathlon, which I never would have thought of on my own. If you hadn’t, I never would have known I could do one. Your post has inspired me to sign up for things as they come up and see where they take me. As always, I am lucky to have you in my life.

    Reply
    1. caritagardiner says:
      February 5, 2026 at 12:55 am

      Back at you!
      My triathlon days are behind me, but maybe we can find something to sign up for together for this spring on next fall. Any ideas?

      Reply
  3. Wonwoo says:
    February 5, 2026 at 2:48 am

    So glad I saw this! I have so many things I’ve been considering signing up for–some I’d enjoy and others I want to avoid–and now I shall!

    Reply
    1. caritagardiner says:
      February 5, 2026 at 12:15 pm

      Please let me know how they go!

      Reply

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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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