Introducing The Medium Writers Challenge

Featuring judges Natalie Portman, Roxane Gay, Saeed Jones, Susan Orlean, and more

Jermaine Hall
The Medium Blog
6 min readJul 28, 2021


Calling all storytellers! When was the last time you read a great piece of writing? What quality made you want to share it far and wide? Why did it strike such a powerful chord? If you were asked to replicate that feeling — to craft an essay that leaves readers caught up in the rapture of an unforgettable narrative — could you do it?

We believe you could. You showed us as much in the past: the Pandemic Reflections writing prompt resulted in hundreds of submissions in the first month. Our call for entries to the #StopAsianHate blog resulted in hundreds of perspectives shared in the first week. And now we want to help discover and nurture great writing again, with The Medium Writers Challenge.

The challenge, which will take place over the course of four weeks, is a chance for you to share your best ideas with an esteemed panel of judges and millions of Medium readers — plus, an opportunity to win $50,000.

Here’s how it will work. We’re providing four guiding prompts: Reentry, Death, Work, and Space. Each is accompanied by a descriptive paragraph to help you get your wheels turning — but don’t feel confined. Your experiences or perspectives might take you down other roads that are well within the parameters of the prompt.

An expert panel of cultural leaders, editors, and writers will join as guest judges to select their favorites. Those judges include Natalie Portman, Roxane Gay, Saeed Jones, Imani Perry, Eve L. Ewing, Susan Orlean, Robert Kolker, kelly corrigan, Dao-Yi Chow, Bonsu Thompson, Julio Vincent Gambuto, Jude Ellison S. Doyle, Kurt Andersen, David Dennis, Jr., and others.

With the help of the judging panel, Medium will select four finalist winners — one for each prompt — who will each be awarded with $10,000 each. One of the four finalists will be selected for a grand prize of $50,000. Additionally, 100 honorable mention selections will each win $100.

Entering the challenge is easy: Just write to one — or more — of the writing prompts outlined below, and include the associated tag when publishing your story on Medium. (Once you hit “Publish” on your post, you can type it into the “Add a tag…” box.)


Tell us about an experience you’ve had coming back to something — or someone — after time away. What changed in your absence? How did you change? What are the funny moments, faux pas, discomforts, and joys that came with returning to an old situation (or your pre-pandemic life) with new eyes?

TAG: MWC Reentry
JUDGES: Imani Perry, Julio Vincent Gambuto, Saeed Jones, Jude Ellison Doyle


People die, of course, but so do other things. Ideals. Relationships. Jobs. Life phases. Pieces of who we once were. A death isn’t always inherently sad, either; sometimes, it’s a positive step, freeing us from what was weighing us down or allowing us to move forward. Illusions can die. Grudges. Bad habits. Tell us about a death you’ve experienced, for better or worse, and how you marked the loss — whether it was with mourning or celebration.

TAG: MWC Death
JUDGES: Susan Orlean, Robert Kolker, kelly corrigan, Eve L. Ewing


“Work” is a term that contains multitudes. Maybe your work is a key pillar of your identity. Maybe it’s the thing that allows you to focus on other pursuits. Maybe it fulfills you; maybe it drains you. Maybe the real work in your life isn’t the same as the way you make money. We want to know what “work” means to you — and the factors that have shaped your thinking. What’s the most important work you do, however you define it? What’s the value of work in your life? What’s your dream job? Is there such a thing as a dream job? Is there a moment, a person, a role that’s changed the way you approach your work?

JUDGES: Roxane Gay, Kurt Andersen, David Dennis, Jr.


Whether we’re letting our imaginations run wild or focusing on what’s in front of us, our day-to-day lives are defined by space: living space, personal space, outer space. We make space. We claim space. We practice social distancing. We turn spaces into homes, into communities, into refuges, and we forge relationships with others and ourselves within those spaces. We wonder, with varying degrees of skepticism and belief, about the beings that occupy the space beyond our planet. However you define it, tell us a story about a role space has played in your life.

TAG: MWC Space
JUDGES: Natalie Portman, Dao-Yi Chow, Bonsu Thompson


In the tag field, start typing the appropriate tag, and it will populate the drop down menu, and you can select it.

You can add a tag to a story in several ways:

  • After writing your draft, you will be prompted to add tags during the prepublish flow, right before publishing.
  • From a published story, click the three-dot menu in the lower-right corner, click “Story settings,” set the tags, and save.
  • From a published story page, click the three-dot menu in the lower corner, click “Edit story,” click the three-dot menu in the top right corner, and click “Change tags,” and click “Save.”

You can only tag your story with a single challenge prompt tag, but can add an additional 4 non-prompt tags. You can submit one story per prompt.

Need some pointers on creating a standout essay? Please register for the Medium-hosted workshop, How to Write an Essay Everyone Wants to Read: 5 Steps to Craft Meaningful Personal Narratives on July 29, 2021 at 4:30 p.m. ET. And be sure to follow our Creators Hub for updates and writing advice over the course of the four-week challenge.

The deadline to publish your work is August 24, 2021. The four finalists and grand prize winner will be announced by October 12, 2021.

For more information please read this FAQ.

To begin writing on Medium, click here.


NO PURCHASE OR PAYMENT NECESSARY. Except for residents in Quebec, Canada, open to Medium users who are at least age 18 (or the age of majority in their jurisdiction of residence, whichever is older) at the time of entry. “Contest Period” is from 12:00:01 a.m. ET on 07/28/21 to 11:59:59 p.m. ET on 08/24/21. There will be four writing prompts made available at the start of the Contest Period. To enter: (i) log into your Medium account; (ii) publish an essay of 500 words or more in response to a prompt; and (iii) tag the essay with that prompt (i.e. MWC Reentry, MWC Death, MWC Work, MWC Space). One entry per person per prompt and four entries total during Contest Period. Submissions will be scored based on: (i) creativity (40%); (ii) originality (30%); and (iii) writing quality (30%) by September 23, 2021. 100 honorable mentions will each receive $100; four finalists will each receive $10,000; and one grand prize winner will receive $50,000. Total Value of All Prizes: $100,000. Odds of winning depend on number and quality of eligible entries. Submissions must comply with the Medium Rules and meet Medium’s Distribution Standards. Contest subject to Official Rules. Details and restrictions apply, so visit here for Official Rules. Sponsor: A Medium Corporation.



Jermaine Hall
The Medium Blog

Jermaine Hall is a digital publishing executive. When he’s not running his two sons and wife from place to place he’s watching Lakers games.