What Goes Into an Award-Winning Essay?

Some notes from The Medium Writers Challenge

Medium Creators
Creators Hub
4 min readOct 20, 2021

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Once upon a time, Medium decided to hold an essay-writing challenge. We hoped this would inspire a lot of people to write, but we didn’t expect to get nearly 10,000 entries! We were committed to reading every single entry, so our crew of curators, staff, and eventually, guest judges, were, let’s just say, very busy for a few months. There were so many incredible entries that we were blown away, and honored that so many people would share their stories with us.

Eventually — evaluating the pieces based on their creativity, originality, and writing quality — we narrowed down a group of semifinalists, finalists, and finally one grand prize winner: “Keeper of the Place,” by Randi Ragan. You can read it below:

This is an unforgettable story, skillfully told — the kind of story that sticks with you long after reading it. Ragan’s tale of what happened to her grandmother and the situations surrounding her grandmother’s strange death was unlike anything else we’d read. The settings and characters are vividly drawn, the imagery indelible, and the narrative is well-structured. (The image of the narrator’s feet on the ground at the beginning and then also at the end! The thread of the theme of place woven throughout! Ach!) The language is both beautiful and controlled and most of all, the essay offers a thoughtful exploration of perhaps the most salient moment in the writer’s life. Writing an essay like this is no joke. The writer has to put her whole heart in it, can’t hold back emotionally, but, at the same time, must have absolute narrative control and know what to edit out — after all, it’s an essay, not a book.

Ragan wrote an illuminating post about her award-winning essay. She points out that she had been processing the events she wrote about for a long time before she created her version:

It’s worth noting that I could not have written this version of the story at any earlier point in my life, certainly not right after my grandmother died. It took a long time for me to think about it, process my feelings toward it, and hold it within me. I feel our stories appear to us on an ethereal timetable that is beyond our dominion. They reveal themselves when we are ready to receive them.

She also describes how she worked to “describe a bizarre, brutal day spent doing dreadfully banal tasks as dictated by the demands of state bureaucracy, with the most beautiful and lyrical language I could conjure up.” Ragan combined her love of language with a difficult personal experience, while also connecting her story to the larger societal conversation happening about mental health and suicide. The weight and texture of a lived life + a larger commentary and communication with the outside world + beautiful writing = a solid recipe for a powerful personal essay!

We can draw out a handful of principles here:

  1. A great essay centers on a key moment — if not the key moment — of one’s life or relationship.
  2. A writer might need a good long time to process a life event before being able to write about it.
  3. Powerful essays combine a couple different layers of narration, often connecting to a larger topic or conversation in the world.
  4. Essays have to take the reader somewhere. When we read, we want some sort of movement, some new knowledge to be revealed.
  5. Essays demand elision. Thoughtful and beautiful writing matter, but so does narrative control and self-editing.

We were fascinated to find out that Ragan is not an established memoirist, essayist, or experienced Medium creator. It’s a beautiful reminder that, as we’re always saying around here, stories can come from anywhere.

Feel like reading more great essays? All the winners of the Medium Writers Challenge are listed here. Many enjoyable hours of reading lie ahead:

Inspired to write? Get started on Medium!

And in case you’re looking for some essay-writing advice, we compiled some here:

Happy writing!

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