Lessons from Success: Bet on Yourself

Happy New Year! Welcome to the final post in a four-post series on the writing lessons I’ve learned from my students’ successes. Today I’m sharing a post I wrote on New Year’s Eve 2015 about doubling down on yourself. A common thread I’ve noticed among students who’ve sold their memoirs: A decision to bet on themselves–to commit some of their time, money, and focus on their writing. This line from Transparent creator Jill Soloway sums up this turning-point choice up perfectly: “I want to double down on me.”

“I Want to Double Down on Me.”

jill soloway
Jill Soloway

I’ve been pretty obsessed with Jill Soloway’s  series Transparent this winter break, which led me to reading Ariel Levy’s interview with Soloway in The New Yorker titled “Dolls and Feelings.”

In the interview Soloway shares that when her career was at its lowest point, she made the decision to “double down” on herself. Even though the sensible thing for her to do at that moment would have been to pay off debt, she decided to bet on herself instead.

An excerpt from the The New Yorker profile, “Dolls and Feelings”:

In 2011, after almost two decades as a television writer, Soloway was broke, with two kids, trying to recover from the recent writers’ strike and the recession. Then her old friend Jane Lynch, who was starring on “Glee,” told her about a job on the show, and Soloway went to meet with the producers. “Finally, here’s this moment where I’m meeting on ‘Glee,’ ” Soloway said. “Ryan Murphy wants to hire me. I’ve been best friends with Jane Lynch for about three decades—we’re sisters. It’s happening.” As Soloway drove home from the meeting, her agent called to say, “Pop the champagne—they loved you.” A week later, he called again: Murphy had heard that Soloway was “difficult,” and wasn’t going to give her the job. The agent said he’d send a check to tide her over.

That night, Soloway sat in the bathtub, while her husband, Bruce Gilbert, a music supervisor for film and television, brushed his teeth. She remembers telling him, “ ‘I don’t want to use the money to pay off our debt. I want to be a director, and I want to make a film with it and get into Sundance. I want to double down on me.’ And Bruce was, like, ‘O.K.’ ” Then, just as Soloway was making the leap to directing her own material, her father called one afternoon and came out as transgender.

Interestingly, Soloway had already been working with the theme of gender identity for years. But at this juncture of her life, her themes met opportunity. I’ve heard this story repeatedly when authors share their books’ origin stories with my classes:
A prior decision to commit to their subject and themes prepared them to seize an opportunity or an insight when it arose.

Often times these writers, like Soloway, first had to overcome a cultural dismissal of their subjects. In a recent interview I did with Cheryl Strayed, she talked about how in grad school the cool topics to write about were drugs, sex, and rock and roll, but the thing she wanted to write about was the decidedly uncool topic of being sad about the loss of her mother. Accepting that her grief was her material was an essential part of her process of doubling down on herself.

What would it look like for you to double down on yourself in the coming year? I’ve been answering that question for myself this past week, and I challenge you to wrestle with it too. Let’s double down together.

Looking for a writing coach? I’m relaunching my coaching business in the new year and have appointments available on Wednesdays, Thursdays, Fridays, and Sundays. Learn more or book an appointment by emailing me at theonestorprods@gmail.com.

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4 Responses to Lessons from Success: Bet on Yourself

  1. Pingback: Lessons from Success: Achieve Your Writing Goals in 2019 - Writing Is My DrinkWriting Is My Drink

  2. Susan M Westlund says:

    Thanks for sharing this and the earlier posts, Theo. You are an inspirational teacher and coach!

  3. Mary Anne Balch Speigel says:

    Thanks for these lessons Theo! Even though I have your book, I have appreciated these four distillations. I have doubled down on myself as writer with time and resources, starting with Yearlong in Memoir in 2017. It has paid off for sure with my short op-Ed published in November and hopefully finishing my memoir in 2019! I could not do it without your teaching, coaching and our HH community!

  4. Cindy says:

    Great advice and plenty to think about. Thanks Theo!

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