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355. Why Preclude Regret

Posted on October 15, 2025October 13, 2025 by caritagardiner
Screenshot 2025-05-11 at 8.50.02 AM

I took the photo above last Spring. Lilacs emit my favorite scent. As we enter the dark months of Winter ahead, I'd like to focus on what comes after: flowers, sunshine, joy. Sometimes, when we have to spend long hours inside, we start to feel trapped. In cages, we seek ways to free ourselves, and if we can't do that physically by going outside (because it's dark and cold and icy), we seek alternatives...and don't always think through the consequences of these options.

While we're making choices about what to do, if we force ourselves to take a moment or two to consider which path will or might later lead us to regret our actions, maybe that's not the right direction to go. I'd argue that it's not always easy to figure out what actions will lead us to the most joy, but it is often easy to know that an option might become a regret. I'd argue that knowing what not to do and not doing it is a huge factor in having a happy life.

Now, if I could just get the teenagers I know to follow this plan...

Do you have good advice about how to prevent regret? Please share ideas in the comments.

4 thoughts on “355. Why Preclude Regret”

  1. Tracy Field says:
    October 18, 2025 at 1:08 am

    I hadn’t thought of it that way. I always tell myself “I want to look back and be proud of how I behaved.” Avoiding regret will take that to the next level…especially when the stakes are high.
    ❤️

    Reply
    1. caritagardiner says:
      October 18, 2025 at 2:13 am

      Thanks, Tracy. Yes, I appreciate both ways to think about how to make choices. Either one will lead to better outcomes than just diving in headfirst without any thought! hugs, cg

      Reply
  2. TvS says:
    November 5, 2025 at 3:44 pm

    This is how I make all hard decisions. Which would I regret, doing it or not doing it.

    Reply
    1. caritagardiner says:
      November 5, 2025 at 6:52 pm

      I just heard a cool podcast about the “Ulysses Method” of asking three questions to decide what to do with one’s life. I won’t say much more about it now because I plan to write a whole post about it later, but at the heart of the questions is what you’ve been asking: Will I regret more doing or not doing this? Smart way to decide!

      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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Read my recent “Why” Wednesday Blog Posts

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  • 358. Why Count Down
  • NetGalley Review of Not You Again
  • 357. Why Embrace the Devil
  • NetGalley Review of We Fell Apart
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