Caroline Cala Donofrio on How To Best Share Our Personal Writing

Read "Confessions of a Mostly Open Book: 10 Tips on Writing About Your Life" where veteran journalist Caroline Donofrio shares her two decades of wisdom on writing the personal essay.

I’m excited to share today’s essay by

Caroline Cala Donofrio

who writes one of my favorite Substacks:

Between a Rock and a Card Place

. She covers everything from friendship to treasured notebooks (which hold more than memories) to the beauty of wandering to reasons to keep going in this sometimes hard-as-heck world and so much more! She also interviews cool people, offers recommendations on her most cherished things alongside a weekly tarot card reading that is life changing.

Caroline has worked at Vogue, WME, Penguin Random House and A Cup of Jo. Her essays have appeared in The Cut, The Washington Post, Refinery29, and The Zoe Report.  She’s the author of the middle grade series Best Babysitters Ever and has worked as a collaborator on nearly a dozen books, including multiple NYTimes bestselling memoirs by notable people.

In other words, Caroline knows a thing or two or ten about writing. So, I’m happy to share her brilliant insights!

Confessions of a Mostly Open Book

10 Tips on Writing About Your Life

I’ve always found it ironic that I share for a living. I come from a notoriously private family who holds their cards (and their feelings) tight to their chests. While I do believe there is a place for privacy, I am of the mind that sharing is our sacred duty.

For as long as I can remember, other people’s stories have kept me company. Whenever I encountered a challenge, I searched for a book or essay by someone who’d been there. Brave words helped me feel seen, counted, and understood. Perhaps it’s no wonder I was called to do the same.

In my twenties, I found my way to the publishing industry, first as an assistant at a literary agency and eventually as an acquiring editor. I loved these jobs—shaping stories, sharpening sentences, helping artists chart their careers. But the more I worked with writers, the louder the truth became: I secretly wanted to be them.

Two competing voices whispered inside me: “Why me?” said the first. “Why not me?” challenged the second. (They dance within me to this day.) Personal writing seemed confined to the world of celebrities and athletes and titans of industry, or else celebrated literary figures. Memoir, I believed, was the dominion of outliers. And I was decidedly not.

Then along came the internet and with it a culture of sharing. These days, the question is not whether we share, but how? To that end, here are ten things I’ve learned about personal writing, from essays to captions to books.  

1. You do not need to be an outlier.

When I sit down to write, I am often plagued by that old question: “Why me?” But then I remind myself of all the words that made a difference in my life—on love and grief and fear and triumph—and how they were all penned by people. You have a story to share, and you needn’t have experienced an alien abduction or won Olympic gold or scaled Kilimanjaro to be worthy of telling it. You are a human appealing to humans. That is more than enough.

2. No one will say it quite like you.

It can be tempting to take stylistic cues from the voices that inspire us. After all, from the time we are eight months old, mimicry is how we learn. But the truth is, your voice is the most powerful one you can employ, because no one else has it. Sometimes, if I’m struggling with getting the wording right, I’ll speak it instead. Reading out loud has a way of plunging the words quite literally into your voice. Does it sound like you? Does it feel natural? Does it ring true?

3. Everything is a conversation.

A personal essay is a conversation between the person you are when you begin it and the person you become by the end. You don’t need to know all the answers at the outset; your future self will lead the way. Likewise, some of the best personal writing feels like a conversation with a friend. The reader is invited to witness this shift, coming on a guided tour of your discovery. By the end, they too are changed, though their destination may be quite different.

4. Everyone loves an underdog.

The most popular, well-received pieces I’ve shared over the years have all been crafted in the wake of some struggle, failure, or misfortune. (Multiple writer friends have shared the same.) Readers enjoy a peek behind the curtain, to know they’re not alone. It’s a bit like the appeal behind hot mess reality TV—we all want to feel better about ourselves, and what better way than by commiserating? Obviously, I don’t advocate that anyone exploits the challenges in their life, nor that they fabricate or exaggerate misfortune. What I am saying is that if you’re holding onto that story about a rejection, heartbreak, or foible because you fear it may invite judgment, please know: sharing it is a gift.

5. Personal writing is not the same as crowdsourced therapy.

The English poet Radclyffe Hall wrote, “Writing, it was like a heavenly balm, it was like flowing out of deep waters, it was like the lifting of a load from the spirit; it bought with it a sense of relief.” And, sure, the act of writing can be balmy as f*ck. But the writing we do when we’re going through it is not necessarily fit for public consumption. In my own practice, nothing gets shared until I am safely on the other side of it. Writing requires perspective. It also requires one to be secure in their convictions. If I’m in the process of working through something, or looking for validation or feedback, it’s not yet time.

6. Dig deep and don’t hold back.

In the world of memoir, it is said that good writing is what you’re scared to share with others, while great writing is what you’re scared to share with yourself. So ask yourself: What are you scared to confront? What are you afraid to acknowledge, let alone broadcast to all of creation? That may be where your best work lies. To quote the incomparable Annie Dillard:

“One of the few things I know about writing is this: spend it all, shoot it, play it, lose it, all, right away, every time. Do not hoard what seems good for a later place in the book, or for another book; give it, give it all, give it now. The impulse to save something good for a better place later is the signal to spend it now. Something more will arise for later, something better. These things fill from behind, from beneath, like well water. Similarly, the impulse to keep to yourself what you have learned is not only shameful, it is destructive. Anything you do not give freely and abundantly becomes lost to you. You open your safe and find ashes.”

7. Vulnerability is not the same as baring all.

I’m often shocked when people thank me for my vulnerability because I’m aware of how much I don’t share. I may divulge an old embarrassment, a dark feeling, a deep heartbreak. But I rarely share the minutiae of my days or the happenings in my personal life, at least not as they’re unfolding. That’s what feels comfortable to me, and in my experience, creates my best work. Others take a different tack, to great success. The point is: You choose what you reveal and you choose how you share it. You may be limited in what you can say because of your job or personal circumstances. That’s okay. You don’t need to expose every skeleton in your closet to be a compelling writer. You only need to open your heart.

8. Their reaction is none of your business.

You owe it to your audience, and to yourself, to make your point in a clear and compelling way. That’s all. People will misunderstand. They will project. They will get it wrong. That’s okay. At the end of the day, this isn’t a PR piece with a targeted agenda; it’s a work of art. An attempt at connection. Someone saw themselves reflected in your words. They felt something. Congratulations—you have done your job.

9. Sharing is a sacred duty.

The next time you find yourself asking, “Why bother?” remember Sean Thomas Dougherty’s poem with the same title. 

Because right now, there is
someone
out there with
a wound
in the exact shape
of your words.

Whether you consider writing to be your hobby, your job, or your greatest love does not change its value. Nor will it dampen the synergy that happens when your words—your internality—meet another’s mind. This is nothing short of magic.

10. Write your own rules.

These tenants are what work for me, in my experience, until this point. Your findings may be different, and that’s okay. Writing, especially online, is always shifting terrain. (As I like to remind myself, Didion did not have to produce a personal essay, in real time, every week.) We live in a culture of clickbait and memes and overwhelm. But writing is different. Celebrate everything it can do and be and offer. Embrace everything at your disposal. Style and meter and punctuation. Use your words. Take it slow. Experiment. Have fun. There are no rules, nor constants—make it up as you go.

Tell me…

Whose personal writing has helped you through hard times?

Do you read your writing out loud? Does it help you find your voice?

How comfortable do you feel sharing your rejections, heartbreaks, or foibles?