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Overcoming Writer's Block: Six Weeks, Six Essays Online Workshop with Chloe Caldwell, Starts January 9th, 2023
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Overcoming Writer's Block: Six Weeks, Six Essays Online Workshop with Chloe Caldwell, Starts January 9th, 2023

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Class Starts Monday, January 9th, 2023


Class will use our online class platform, Wet Ink, and also have a welcome Zoom meeting on Monday (1/9 at 7PM EST).

Any questions about this class? Use the Chat Button (lower left) to talk with us.

Led by Chloe Caldwell, author of of three books: the essay collection I’ll Tell You in Person (Coffee House/Emily Books, 2016), the critically acclaimed novella, WOMEN (SF/LD 2014 and Harper Collins UK, 2017) and Legs Get Led Astray. Her memoir, The Red Zone: A Love Story, was published in April 2022 from Soft Skull. Read her work in the The Cut, NY Times, Vice, Salon, Longreads, Nylon, Bon Appétit and many more publications.

In this generative class for writers of creative nonfiction, you will explore different tools for times when you feel blocked or overwhelmed about where to begin.

Class is structured around a series of fun and bizarre writing prompts designed to lead you to your best work, as well as compelling readings that correspond to the prompts and motivating video lectures in which I share writing tips and advice for breaking through creative blocks. 

Writers will leave class with six wildly varied essays to expand upon, and with a keener sense of how to move forward next time you’re stuck in a project. Chloe will provide encouraging and constructive feedback on all six prompts, and will give each student individual reading lists and personalized advice on publication (from outlets to the submission process) at the end of class.

Students will receive feedback from Chloe, as well as their fellow classmates. 

  • Week 1: Beginnings and Endings    
  • Week 2: Abandoning Form     
  • Week 3: Writing What You Don't Remember    
  • Week 4: Place and Setting as Character    
  • Week 5: Your Voice On Steroids     
  • Week 6: Submitting and publishing
  • *Syllabus subject to change   
  • Six new essays
  • New strategies for getting unstuck
  • Exposure to new readings and authors
  • Personalized reading list and suggestions of where to submit
  • Writer friends
  • Excitement and confidence in your writing practice   


  • You're bored with your writing practice
  • You're ready to generate new material 
  • You're open-minded to outside-the-box techniques 
  • You want to shake things up
  • You want strategies and techniques you can use forever in your writing practice


"The generative work I did in your class led to my first published essays, first at Hobart and then The Cut. I've gone on to publish at a bunch of outlets I never thought would be attainable for me. Whenever anyone asks me about my "journey" I always tell them about your class and how it changed my life. I will be forever grateful to you for, among other things, giving me the tools to find the story."—Anna Shults Held 

"Chloe’s classes changed my life. She is so honest, thoughtful, and enthusiastic about her students and their work. She attracts smart, funny, open people to her classes. I’ve taken nearly a dozen workshops with her now and I consistently walk away feeling energized, inspired, and like I’ve known the people in the class for years. Chloe’s guidance, support, and genuine interest in her students gave me the courage to take my writing seriously. I’ve learned so much from her and can’t recommend her workshops highly enough." – Emily Smith, former student

"Chloe is a dreamy writing teacher. As an editor, she is precise and discerning, and she has a knack for mining insights from even the roughest of drafts. She’s also kind and compassionate, building our confidence to tell our stories. Her classes are engaging and generative: I have found new favorite writers from essays we read together, and started several new pieces from in-class prompts." —Jasmin Sandelson, former student

"Everything I know about good writing I know from Chloe. She helped me get published for the first time on Longreads. Her feedback is invaluable and elevated my writing to a whole new level. I’d be hard pressed to find someone with writing prompts and reading assignments as unique and powerful as hers. I always tell everyone, if you want to expand your writer’s brain, talk to Chloe." – Vanessa Golenia, former student

"I first became acquainted with Chloe through her writing, and was so excited to find that the combination of heart and discernment I love in Women and I’ll Tell You in Person also comes out in her teaching. Her edits are sharp and her ideas for opening a piece up are plentiful–she’s helped me gain a lot of confidence and drive when it comes to drafting, rewriting, and editing my own work." – Audrey Moyce, former student

"My mentorship with Chloe Caldwell was truly my greatest workshopping experience yet. As a professional copywriter, essay writing has become a passion project I do on the side for my own fun, and hadn't much considered publishing until Chloe gave me the confidence to pitch to my dream publication—and they took it! From her extensive and wildly helpful in-line edits to just chatting on the phone about my seemingly endless ideas, Chloe's mentorship has left me a better, more confident, and more inspired writer. Run! Don't! walk! to sign up for her next mentorship." -Emma T., former student

You can pay for the course in full or use Affirm to pay over time with equal Monthly Payments. Both options are available at checkout.


This class is entirely asynchronous which means you complete the weekly assignments on your own schedule. There are no set meeting times in order to allow for greater participation; your cohort will consist of writers from across different time zones, which allows for a wonderful diversity of voices.

Along with your weekly deadlines there is plenty of interaction with Chloe and your peers within Wet Ink, our dedicated online classroom. Craft materials, lectures, reading assignments, and writing prompts are all available through the online classroom. Students also post work and provide and receive feedback within the online classroom environment.

You can get the work done as you see fit week-to-week, so it is perfect for any schedule. There are discussion questions each week inspired by the assigned readings and topics in the lecture notes. Students are encouraged to take these wherever is most compelling and/or useful for them. Chloe engages with these discussions throughout the week and you will receive feedback from all assigned writing activities.


Wet Ink was built and designed specifically for online writing classes. Wet Ink is private, easy to use, and very interactive. You can learn more about the Wet Ink platform by Watching a Class Demo.

  • Instructor: Chloe Caldwell
  • Class size limited to 10 writers
  • Starts January 9th, 2023
  • Course is fully ONLINE and will meet via Wet Ink

Instructor Chloe Caldwell is the author of the essay collections I’LL TELL YOU IN PERSON and LEGS GET LED ASTRAY, as well as the critically acclaimed novella, WOMEN. Her memoir, THE RED ZONE: A LOVE STORY, published on April 19th, 2022 from Soft Skull. Chloe’s essays have appeared in The New York Times, Bon Appétit, New York Magazine’s The Cut, The Strategist, Buzzfeed, Longreads, Vice, Nylon,, Medium,The Rumpus, Catapult, Hobart, The Sun, Men’s Health, The Nervous Breakdown, and half a dozen anthologies including Goodbye To All That: Writers on Loving and Leaving NYC and Without A Net: The Female Experience of Growing Up Working Class. Her essay “Hungry Ghost” was listed as Notable in 2017 Best American Non Required Reading. Chloe lives in Hudson, NY.