Caroline Leavitt

In today’s episode, Brooke and Grant tackle the side hustle—why all writers do it, how to make peace with it, and how and why now is the best time ever for writers to actually have a writerly side hustle (as opposed to a 9-to-5 job). Guest Caroline Leavitt shares how she pieces together her worklife, multitasking and creating and making ends meet, and gives both encouragement and a dose of the reality of “making it” as a modern writer/author.


Caroline Leavitt is the New York Times and USA Today bestselling author of Is This Tomorrow, Pictures of You, Girls In Trouble, Coming Back To Me, Living Other Lives, Into Thin Air, Family, Jealousies, Lifelines, and Meeting Rozzy Halfway. Her books have been optioned for film, translated into multiple languages, and condensed in magazines. Her ninth novel, Pictures of You, is a New York Times bestseller and a Costco “Pennie’s Pick,” among its multiple other accolades. Caroline has been a judge in both the Writers’ Voice Fiction Awards in New York City and the Midatlantic Arts Grants in Fiction. She teaches novel writing online at both Stanford University and UCLA Extension Writers Program, as well as working with writers privately. She lives in Hoboken, New Jersey, New York City’s unofficial sixth borough.

The Takeaway: Connect with Another Aspect of Self

This exercise comes from Liz Gilbert, and it’s this—to write a letter to yourself from some aspect of yourself that wants to have a voice. Liz’s book, Big Magic, is divided into sections—Courage, Persistence, Divinity. So you might start here. To write a letter to yourself from your courage, from your persistence, from your divinity. Write the words: Dear _____ (your name). Then you follow with: I am your courage. Or I am your persistence, or I am your divinity. From here, give voice to this aspect of yourself. You see what it holds for you. You can give voice to any aspect of self—inspiration, curiosity, you name it, even so called negative voices, like anger or resentment. Write a letter to yourself, and if you like it, write more. Discover the inherent wisdom of the many aspects of yourself.

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