Online | Nonfiction | Workshop

Six Weeks, Five Essays: Overcoming Writer's Block

In this generative class for serious writers of 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 writing prompts designed to lead you to your best work, as well as readings that correspond to the prompts and motivating lectures in which I share writing tips and advice for breaking through creative blocks. 

Writers will leave class with five wildly varied essays to expand upon, and with a keener sense of how to move forward next time you’re stuck in a project. At the end of class, I will provide encouraging and constructive feedback to each student in the form of an editorial memo that addresses all six prompts–this note will include individual reading lists and personalized advice on publication (from venues to the submission process). Students will also give and receive feedback on each other's work, and we will discuss the work submitted in our weekly live chats.

This class will meet over our text-only chat platform. There will not be any video or audio component to class.


- Drafts of five different personal essays

- Detailed feedback from your instructor and your fellow classmates

- Access to generative writing prompts

- Tips for moving past writer's block

- Access to Catapult's list of writing opportunities and important submission deadlines, as well as a 10% discount on all future Catapult classes


Week One: Voice

Week Two: Perspective/Point of View

Week Three: Setting

Week Four: Theme

Week Five: Reshaping the Past

Week Six: Pitching & Publishing

Chloe Caldwell

Chloe Caldwell is the author of The Red Zone: A Love Story, the critically acclaimed  novella WOMEN and essay collections I'll Tell You in Person and Legs Get Led Astray. Her essays have been published in The New York Times, Bon Appétit, The Cut,  Longreads, NylonBuzzfeed, and more. She lives in Hudson, NY. 


"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 was my first writing teacher in NYC, and I continue to follow her and her classes around like a writerly puppy. Not only are her classes rewarding, but she’s also a great writer to follow in the footsteps of! I mean, have you read Women?! She gives really good critiques and has the ability to find out what you need as an individual, rather than try to mold you into something she thinks you should be. She’s totally honest without being a dick. Her writing exercises are great too, and I am still hanging on to the fantastic handouts she gave us. Highly recommend any of her classes! "

Janna Jesson former student

"WOMEN by Chloe Caldwell is a beautiful read/a perfect primer for an explosive lesbian affair/an essential truth."

Lena Dunham actress and writer

"Prepare to shed skin. Chloe Caldwell’s essays will dare you to dissect your own life. Shot-through with sexuality and sass, her language will get up in you and turn you inside out in the best possible way."


"Chloe Caldwell’s LEGS GET LED ASTRAY is a scorching hot glitter box of youthful despair and dark delight. Tender and sharp, wide-eyed and searching, these essays have a reckless beauty that feels to me like magic."

Cheryl Strayed author of WILD and TINY BEAUTIFUL THINGS

“Chloe Caldwell has written the ideal 'female companion book'—meaning, while reading, I felt like I had a female companion with at all times. On the subway, I had my female companion. In my backpack, I had my female companion. On the sidewalk, I held on tight to my female companion, and pedestrians would stare at her, so boldly yellow in my hands. Pretty soon my female companion took up residency in my head. She helped me process the world with sass, spite, sympathy, and wit. I don’t know what could be better than a book that allows you to be alone but to never feel lonely. I’LL TELL YOU IN PERSON does this and more. It projects the most potent afterglow, and Caldwell is a writer beyond gifted and generous. She is like a sage.”

Helen Julavits author of THE FOLDED CLOCK

"One of the most endearing and exciting writers of a generation."


"Chloe Caldwell writes with an emotional intensity that is insightful, heartfelt, and often hilarious. In her new essay collection, I'LL TELL YOU IN PERSON, she perfectly captures what it’s like to try and navigate your way through the traumatic first decade of adulthood. It’s filled with a raw honesty and voyeuristic allure that’s utterly captivating." bookseller

"Everything I know about good writing I know from Chloe. She helped me get published for the first time on Long Reads. 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

"I started working with Chloe five years ago and she has guided my work ever since. She is a generous and gifted teacher. I can hear Chloe's voice as I write, reminding me to find action, add in details and remove words I don't need. Her feedback is gentle but precise, and she has a way of building community in all her classes. You will leave a better writer, and with new writer friends. I can't recommend her highly enough."

Jillian Eugenios former student