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337. Why Not Fit In

Posted on June 11, 2025June 10, 2025 by caritagardiner
Screenshot 2025-01-01 at 12.17.52 PM

I'm fully aware that there are two ways to read the title of today's post. First, I could be asking the question, why not (try to) fit in? Well, there are lots of reasons, some of which I hope you already know and others this post might make clear. I'm thinking about the second way to read the title. I'm advocating a life of not trying to fit in. I got the idea from listening to the banter on the podcast episode linked to the photo above.

The three hosts talk about the difference between belonging and fitting in, and as I've been thinking about providing as much sound life advice as I can to the 2025s (and any other young people) who might have started reading this blog, I think keeping the distinction in mind is a key way to a happier life.

To live a fulfilled life, humans need interpersonal connections. In the best possible scenario, all of our relationships would nourish us, and all of the people in our lives would support us. Every interaction would buoy our spirits. Generally, I'd guess that we gravitate to those we believe will make our lives happier, but I don't think that we're always correct about who those people are. We might think that being among those who are doing super cool things is the ticket to happiness and fulfilment. If so, we would try to fit in with these cool cats who lead exciting, extravagant lives.

If I decide to play the part of the people I admire, shaping myself in ways I hope they will admire back, I might fit in with them, but I will lose myself. By acting only and forever as my true, best self, I will weed out the people who don't want to spend time with the real me. I with find those with whom I belong.

We should all aim to find people who esteem what's real within us. We should spend time with those who see through the fitting in right to the heart.

Have you found that belonging is better for you than fitting in? If so, what ways have you discovered to find those with whom you belong? Please share your ideas 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

  • 338. Why Find Your People
  • NetGalley Review of Look Before You Leap
  • NetGalley Review of Sunny Side Up
  • 337. Why Not Fit In
  • 336. Why SFAH
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