Author: Kelly Caldwell

Sometimes at this time of year, I like to write to you all about love stories — how not to make them sappy and cringey. Or how to write a good love letter. Or writing a favorite setting that cracks your heart open and makes you feel like you can fly.

Why is love so challenging to write about? My crackpot hypothesis is because it’s so loaded and so fraught. Our desire for it to resonate with the reader, our need for their hearts to swell, or break, is so intense, it can get in the way of us writing these moments well.

Or I could be wrong. Once I asked the author Roger Rosenblatt why writing about love is hard, and he said, “It’s not.”

“There’s nothing special or different about writing about love,” Rosenblatt said. ““You just have to be a good writer—a good writer can write about anything.”

And what’s the key to being a good writer? That’s right. Rewriting.

This week, in her Substack Badreads, the author Lauren Hough wrote something about craft that applies directly to this question, and I love it so much, and it’s so true, I’m just going to share it here in full:

I wrote about it so many times, whatever it is. I wrote about it so that I could practice the reality of it. So that I could see it on the page. So that it could have a place to exist. Then I wrote it again and tried to understand it. Then I wrote it again and tried to make it sound right, the way I wanted it to sound. I wrote it again to punish myself. Then I wrote it to punish those at fault. I wrote it to punish the reader. Because I was angry. Then I wrote it again and tried to see if there was a reason to write it at all. Did it matter. Did it fit the story. Could I write it in a way that I would want to read it. And mostly, when the answer was no, I never wrote it again. But if I thought there was a purpose, I wrote it again and sent it to my agent or editor. Then I wrote it again to make it funnier, or whatever it needed to be.

People love to say there are no do-overs in life. Those people are not writers. We know the truth, though. If you want to do anything well, (like writing), you not only have to believe in do-overs, you have to embrace them.  

Kelly Caldwell

Dean of Faculty

Every morning, the author Athena Dixon starts her day on a text thread with her parents and her sister: “Good morning.” “Have a good day.” “Love you.”

Here, already, you’re probably thinking, “That’s nice, Caldwell, but I thought this is supposed to be writing advice…?” Wait! It is! Because the Dixon family’s heartwarming daily tradition started after Athena published her book The Loneliness Files last October.

“My family and friends—I didn’t give them enough grace and enough love to understand that they would be here for me in any capacity I needed them to be, because I was so used to being hyper-independent,” Athena said in a visit to my class last month. “It took me putting my words into the world to really ask them for what I needed from them.”

When it comes to writing our stories, and putting them out in the world, it sometimes feels like we spend a lot of time imagining the worst outcomes. Students air their fears about this in class all the time. I wrote about it for the Writer magazine once, and so did my colleague Melissa Petro (who once got fired after publishing one of her stories). Heck, next month, I’m going to moderate a whole panel at Gotham’s nonfiction conference about managing hot-button topics and sensitive family members.

I’m not saying there’s nothing to fear. I’m saying, maybe we don’t talk about the good stuff enough.

And Athena’s experiences with her book are solid evidence that there’s lots of good to talk about. She started out simply trying to chronicle what it was to live alone during lockdown in 2020, but quickly, as most writers do, she found herself examining the experience, and then researching loneliness and its after-effects, the way it’s spreading through our culture.

And that’s the where the first really good thing happened. She understood herself better.

“Writing the book, it allowed me to kind of lay all these things out on a page and for the first time in my life look at them very starkly, and figure out what part was useful for me, what part is a hindrance to me,” Athena said. “Then by the time I get to the end of the book, I’m discovering for myself that I think there’s no solution to my loneliness. But I think there’s usefulness in it. I think I know now when I’m hiding in it, and coming up with my own toolkit on how to navigate that.”

Once she dissected her life and stitched it back together again, a story started to take shape, she said. And then a book. Her early drafts helped her secure a residency at Tin House, where she connected with Hanif Abdurraqib, an editor-at-large with the prestigious independent press Tin House Books. Abdurraqib would eventually acquire, edit, and publish her book. Which led to a book tour, and connecting even more with the writing community. And also to more honest conversations with her loved ones about leaning on each other. And a new family tradition.

Then, most recently, it led last week to Athena signing with an agent, Danielle Bukowski at Sterling Lord Literistic.

I’m skipping over the hardest parts here, especially how painful it is to dissect your own life, as Athena did, as writers do. I’m skipping over the part where Athena struggled with depression during the long, lonely lockdown months. I’m skipping over the many rejections she’s racked up in her career.

Athena doesn’t skip them, though. “Everything that I write that I put into the world is something that I’ve sat with and said, ‘I’m okay with people talking to me about this, I’m okay with people asking me about this, interpreting it, liking or disliking it,’ ” she said. “That’s how I buffer myself.”

The hard stuff, the risks, are always there. And that’s good, in its way, too. Because it’s the hard stuff — the uncomfortable truths we excavate, the failed first drafts, the flashbacks and setbacks — that make our victories so much sweeter.

Kelly Caldwell

Dean of Faculty

“*HOW* do you guys decide which story gets told first? I can’t tell which story should get my time and energy, my brain hurts, and I tend to visit Tangent Town because that is how my brain likes to play.”

This question came from a student recently, who’s struggling with the opposite of writer’s block, what she’s calling “writer’s firehose.”

Usually, my go-to advice for writers struggling with their stories is to let the subconscious have its way. But that won’t help my student, because her subconscious is firehosing ideas all over the page, dragging her to Tangent Town, and basically not letting her finish anything. And she really wants to finish something.

And look, we’ve all been to Tangent Town. It’s that brain space where too many ideas live, all clamoring to escape. Sometimes, it’s exactly where you want to be. There are days you need firehose your ideas all over the page, (yes, firehose is my new favorite verb). You want to let your subconscious excavate a long-forgotten memory, or take your protagonist through the entire Illinois State Fair (for some reason), or obsess about avocado farms. There are days your subconscious will throw a tantrum and block the exits if you don’t.

But we choose to write because we have something to say. So I say, some days, you get to choose. You can decide that your subconscious is not—and should not—be the boss of you. On those days, tell it to go sit in a chair, as my colleague N. West Moss will do, while you have your say.

Recently, Mary Karr has been posting about writing a memoir about her sister, and in these posts, we watch her wrestle with these exact issues in real time. Sometimes, Karr is very deliberately driving the bus; others, she’s letting her mind tell her where to go; still others, both her conscious and subconscious mind labor together for three hours to produce four good sentences. Check out some of Karr’s posts here.

I think I’m trying to give you different colored permission slips to do what you need: A pink one for when you need to focus on something urgent and get it out; green if you need to make a deadline; azure when you want to commandeer a chair and tell your dead grandmother to shush; orange if you just want to open the firehose to its widest setting, and see what comes out.

Try this: open your notebook, close your eyes and see what happens. Nothing? OK, look at the most recent thing you wrote and pick up where you left off. Following the thread of something that hooked your interest can be a good way to wade back into the flow, even if you don’t write something you want to keep later. 

Or? Decide at the end of a writing session exactly what you’ll work on during your next one, ie, “Next time, start with the story about Dexter and the platypus.”  

But if writing about Dexter and the platypus feels like a chore, don’t force it. Shuffle your permission slips and move on. 

Whatever it takes, keep the traffic flowing in one direction. Never forget, you are the mayor of Tangent Town.

Kelly Caldwell

Dean of Faculty