In her first essay collection, Legs Get Led Astray, Chloe Caldwell brings together tales of love affairs, obsessions, babysitting, and Brooklyn to create a disarming portrait of a young woman’s life.

When you’re writing about masturbating, having an orgy, trying heroin, or pretending the guy you're having sex with is James Frey, how do you get to that place of complete honesty? Were you worried about what your family would think?

I don’t think about my family when I write. If I thought about my grandma when I wrote, it would give me a buzzkill. I get to that place by going with my instinct. By putting on headphones and going underwater and letting the words come. Sometimes it makes me feel manic or sick or sad or elated, but that’s how I do it.

How did you go from writing personal essays to realizing there was a book here?

My friend Aaron and I agreed that we would send each other 200 pages by the end of October in 2010. So I put my finished pieces into one document, printed it out, and mailed it to him. From there I revised, replacing weaker writing with stronger. I knew I wanted to do a collection, but it wasn't easy to find a small press that was looking for essay collections.

How did you find Future Tense?

My friend Sean H. Doyle told me about them when I was living in Seattle in 2010. I emailed Kevin Sampsell and he said he was swamped. A year later, he emailed me and said, “Send me stuff now.”

What appealed to you about working with a small press?

I didn't do the agent search, because Kevin emailed me quite literally when I’d just made my manuscript into something real. After I submitted to him, I wrote maybe 10 new essays and replaced the old stuff with the new. Small presses seemed more accessible. It was the most serendipitous thing that's happened in my life so far, hands down.

What was the process of getting the book published?

My experience was profoundly pleasant. I had the best time. Kevin, Bryan Coffelt, (designer/assistant editor), and I were making the magic happen. Staying up late, cramming and editing. There was something special about that. I had my say in everything. They called me after they emailed me the choices for book covers. I started crying when I saw what became the final cover. As for publicity, Kevin told me from the very beginning that with a small press, a lot of a book’s success is dependent on how much work the author does.

How did your friendship with Cheryl Strayed affect your experience as a burgeoning writer?

I love Cheryl, and I think our relationship has more to do with the way we are as people, than with our writing. She was one of the first writers I knew to believe in me. When Kevin solicited me for Leg’s Get Led Astray,I thought Cheryl had put a word in for me, though that turned out not to be the case. I think mentors are great, and I hope to extend the generosity she's given me to others.

The essays in Legs Get Led Astray are very much meditations on themes from a certain era in your life; what’s next?

I’m working on a piece called “Roommates—” it’s about living with my dad and being a 26-year-old female. There are so many memoirs out there about bad relationships with parents. But what if you had a good relationship with a parent? Where does that lead you? I want to challenge myself stylistically.