Breaking In: Debut Author Jacob Tobia on the Memoir Process and More

In our Breaking In column in Writer’s Digest magazine, we talk with debut authors—such as Jacob Tobia (jacobtobia.com), author of the memoir Sissy—about how they did it, what they learned and why you can do it, too. In this unabridged interview, Tobia discusses making the leap from writing personal essays and op-eds to a full memoir as well as the importance of building a platform to promote your work.

Tell us about Sissy.

Sissy is the story of how I reclaimed my gender from a world that sought to take it from me. It is the story of how I reconnected with my femininity, took control of my destiny, and—at the tender age of 21—struggled to figure out how lipstick works. I’m still working on that last part.

Where do you write from?

I live in Los Angeles, but wrote almost the entirety of Sissy from my childhood home in Raleigh, N.C. There was something important for me, something sacred, about writing the book in the place where it all happened.

Briefly, what led up to Sissy? What were you writing and getting published before breaking out with this book?

I have been writing personal essays, publishing op-eds and blogging for six years or so before I sold Sissy. I started locally, with a queer blog that was run by the LGBTQ student group at my undergrad, then quickly made my way to the Huffington Post, before finally being paid to write by BuzzFeed, TIME, The New York Times and many others. It was a slow build, but at some point, I grew tired of telling only snippets of my gender journey. I wanted to tell the whole thing, to write the full arc of it and tell each vignette in context of the greater story, which is why I decided to write this book.

What was the time frame for writing this book?

Sissy took me about two months to draft and a month and a half to edit, but that was spread over about a year and a half. I started writing Sissy when I was working on “Transparent” and it was crazy because I would wake up at 6 a.m., head to the café near my house at 7 a.m. and write for two hours before heading to set to work a 12-hour day as the director’s assistant and social media producer. I don’t know how I had all of that energy—just thinking about it today wears me out.

Guide to Literary Agents 2019

How did you find your agent?

My agent (the unconquerable Katherine Latshaw at Folio) actually came to me! I’d been unsuccessfully pitching agents for about a year when Katherine emailed me out of the blue. A lot of the agents I’d spoken to previously were treating me as a “social media influencer” and not as a literary voice, but Katherine couldn’t’ve cared less about how many Instagram followers I had. She was interested in cultivating my voice and my writing, not my brand, so we hit it off instantly. She gave me permission to set my humor free and be as irreverent in my storytelling as I could. And, like me, she’s also from North Carolina and wears dark lipstick, which is how I knew we’d get along flawlessly.

What were your biggest learning experiences or surprises throughout the publishing process?

Honestly, I didn’t anticipate how healing the writing process would be. I’d been walking around with all of these identitarian injuries for most of my life, and writing Sissy finally pushed me do the physical therapy I’d been avoiding for years. There is something profoundly powerful about centering yourself as the protagonist of your own life in book length. It changes you. You feel whole and more yourself after doing something like that. I wouldn’t give that up for the world.

Looking back, what did you do right that helped you break in?

I didn’t realize it until I sat down with my publicist to make a press kit, but before I broke in I did an incredible job getting publicity for my work. Without realizing it, I was working as my own publicist, cultivating lasting friendships with journalists, building relationships via cold outreach and ensuring that by the time I sold Sissy, I was already an established voice in the trans community.

On that note, what would you have done differently if you could do it again?

If I could do things over again, I would’ve paid a little bit more attention to word count when I was writing my first draft of the manuscript. On my first pass, I simply wrote what I felt I needed to say, so the first draft of my manuscript came in at 167,000 words. My editor Helen called me and was very politely like, “So if we publish this, it will be 700 pages in book form, which is a touch long for a debut memoir.” And I was like, “OMG WHAT?” I’d just written my outline without paying attention to word count. Without realizing it, I basically wrote two books instead of one. So I wouldn’t necessarily recommend that approach to other authors if you’re trying to be efficient. That being said, I think that over-delivering like that ensured that, by the time we cut it down, we had some incredible material to work with.

Did you have a platform in place? On this topic, what are you doing the build a platform and gain readership?

I already had a substantial following by the time I sold Sissy—an active readership of queer and trans and allied folks who cared about my words and my storytelling. I built this through the one-two punch of 1) publishing a minimum of six to 10 personal essays a year and 2) perfecting my strategy for ensuring that people read my work. I learned very early on in my career that, no matter how brilliant your work is, you still have to promote the hell out of it. You can never rely on an essay going viral based on its merit alone. It’s important to put as much work into your PR and social media strategy as you put into your writing, and if that means you have to write less often, it’s worth it. Better to publish six essays a year that you spend the time to properly promote than 12 that you don’t promote well.

What is your best piece of writing advice that we haven’t discussed yet?

In 2014, when I’d just moved to New York City and was completely green on the scene, Janet Mock agreed to grab coffee with me out of the goodness of her heart. I told her that, one day, I wanted to write a book and she was so encouraging and sweet, but she also gave me powerful cautionary advice. She reminded me that you don’t owe everyone all of your stories. It’s OK to keep certain stories just for yourself. It’s OK to have boundaries. It doesn’t mean that you’re a bad artist or that you’re being withholding; it means that you’re human. The best stories to tell are the stories that you are ready to tell.

What’s next? (Upcoming projects? Future plans?)

I have a lot of exciting projects coming up in Hollywood—I’m doing my first voice acting for a show with Dreamworks and Netflix, working on a pilot project for Hulu and have optioned Sissy to Legendary Entertainment for development into a potential television series. There are a lot of exciting things on the horizon. Also, I know you’re not supposed to do this, but I can’t help myself: I’m already beginning to brainstorm book number two…