Sometimes, the hardest stories to tell are the ones that won’t sit still—the ones that keep shifting even as you try to capture them on the page. I’ve always been drawn to writers who embrace that uncertainty, who don’t wait for everything to make sense before they start writing. Chloé Caldwell is one of those writers.

There’s a moment in my TEDx Talk where I reference her essay My Year of Heroin and Acne—a piece that shows what raw honesty on the page can do. I talk about how Chloé circles back at the end of her essay, revealing the transformation she’s made from where she began. So when I had the chance to interview Chloé for Freelance Writing Direct, it felt like picking up a conversation I’d been having with her work for years.

Chloé’s new memoir, Trying, unfolds in brief, piercing vignettes about infertility, heartbreak, queerness, and self-discovery. It’s about all the ways we keep trying—to build a family, to stay in love, to become ourselves again after loss.

Our conversation moved into tender terrain. My own journey to motherhood was filled with longing and unexpected turns before leading to my beautiful daughter. Talking with Chloé, I found myself revealing truths I’d never shared publicly—the fear of failing my own expectations, the quiet grief of what could have been, and the strength it takes to begin again.

In This Episode

• Writing a memoir while still living through it

• The shame and silence surrounding infertility

• Trusting intuition and reclaiming personal truth

• Finding humor and craft in heartbreak

• Ending a story that’s still unfolding

Watch on YouTube

About Chloé Caldwell 

Chloé Caldwell is the author of the novella Women, the memoir The Red Zone, and the essay collections I’ll Tell You in Person and Legs Get Led Astray. Her essays have appeared in the New York Times, Vogue, Bon Appétit, the Cut, MSNBC, Autostraddle, Longreads, and Nylon and in anthologies including Goodbye to All That: Writers on Loving and Leaving New York and Without a Net: The Female Experience of Growing Up Working Class and Sluts. She offers writing support at  scrappyliterary.com. Caldwell lives in Hudson, New York.

Connect with Chloé 

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Upcoming class: Writing Chaos In Real Time

Upcoming Class: Writing Divorce

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Check out Estelle’s mention of Chloe in her TEDx Talk How to Get Noticed in Your Writing and Beyond