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What Kind of Writing Wins Awards?

Insights from lit mag editors from The Sun, Ploughshares, and Okay Donkey

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Rachel Dillon's avatar
steve chang's avatar
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Derek Askey, Rachel Dillon, steve chang, and The Forever Workshop
Aug 19, 2026
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Hey friends,

Welcome to another round of Tell Us Something We Don’t Know… where we source a panel of literary experts and ask them questions about whatever the heck. Today, the heck is award nominations and our instructors are experienced editors from three top-tier literary magazines:

The Experts:

  • Derek Askey — senior editor at The Sun

  • Rachel Dillon — award-winning poet, teacher, and managing editor of Ploughshares

  • Steve Chang — co-founder of Lit Match Collective and fiction editor at Okay Donkey

The Takeaways:

  • How do lit mag editors decide which pieces to nominate for awards?

  • What are the qualities editors look for in an award-winning story or poem?

  • How subjective is the whole process? (And how to deal with rejection)

  • Advice on crafting and submitting your very best writing


Upgrade to access this lesson as well as all our previous ones that’ll help shape your writing career!


By the end of this workshop, you might just be inspired to write an award-winning piece of your own…

Let’s Talk Writing Awards…

Every year, lit mag editors put forward their favorite pieces for a variety of writing awards. It’s a badge of honor and a massive confidence boost for writers, but what goes on behind the scenes? How do editors choose? What makes an award-winning story? (And how can we write one?)

We asked three experienced lit mag editors about the whole process and here’s what they had to say:

The Nomination Process

How does it work & what goes on behind the scenes?


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Derek Askey's avatar
A guest post by
Derek Askey
Derek Askey is a senior editor at The Sun.
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Rachel Dillon's avatar
A guest post by
Rachel Dillon
Rachel Dillon's poetry appears in The Slowdown, the Academy of American Poets' Poem-a-Day, Pleiades, Poet Lore, and elsewhere. A former high school English teacher in NYC public schools, she is Managing Editor of Ploughshares. (rachelmdillon.com)
steve chang's avatar
A guest post by
steve chang
fiction editor at Okay Donkey, co-person at Lit Match Collective, Fellow at various classy institutions
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