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Picture of Sissy Jacob Tobia Interview
Credit: Oriana Koren / G.P. Putnam's Sons

Jacob Tobia is a gender nonconforming writer, producer, and performer with a long list of accomplishments. They’re a member of the Biden Foundation’s Advisory Council for Advancing LGBTQ Equality, they worked as a producer on Amazon’s Transparent, and they hosted Queer 2.0 on NBC News. Now, they can add another title to that impressive list: published author of Sissy: A Coming-of-Gender Story.

Sissy is a comedic memoir about Tobia’s experience growing up as someone who wasn’t sure if they were a boy, a girl, both, or something in between. They wanted to play outside AND play tea party; they wanted a bug collection AND a Barbie collection. But as they got older, the bullying began. Sissy is filled with moments that will both break your heart and make you howl with laughter. One minute, Tobia is coming out to their parents to mixed reactions and contemplating their relationship with God; the next, they’re coming out to Jon Stewart via fan mail and buying their first pair of high heels at Charlotte Russe.

Sissy will challenge the way you think about gender and inspire you to consider your own struggles with gender identity. Because, as Tobia explains, we all have them.

I spoke with Tobia about everything from how fashion can be political to how everyone has experienced gender-based trauma in some form or another. Even if you consider yourself knowledgeable about gender, you’ll still learn a lot from their honest, eye-opening, and truly hilarious memoir. Tobia’s voice is one we all need to hear.

HelloGiggles: Sissy is different from the types of trans storytelling we’re used to. What can readers expect from it?

Jacob Tobia: Sissy is a foundational transgender story. It is a comedic memoir about how, growing up in Raleigh, North Carolina, I came to understand my identity as a sissy, a queen, a queer femme, and a gender noncoforming trans person. But it’s not an “earnest” or “precious” take on that experience; the book doesn’t arrive at any convenient conclusions or Hallmark moments. If anything, Sissy is a rebellion against mainstream pressure to remove the rough edges, to make my trans story “more digestible” or “easier to understand.”

Instead of cleaning up the rough edges, Sissy is based on the principle that the mess is the best part. It is less the story of how I went from “one gender” to “the other” (as if such lines can be drawn in the first place) and more the story of how I buzzed about between genders for years, collecting as much pollen on my haunches as I could. It’s my hope that this book will encourage everyone (not just trans/gender nonconforming people) to consider their own coming-of-gender stories. We all have one to tell.

HG: You use they/them pronouns. What do you say to people who don’t understand why having they/them as an option matters?

JT: “They” and “them” are pronouns for everyone. Anyone can use they, because it’s neutral and fabulous and doesn’t come with any gender expectations whatsoever. If you feel at all confined by “he” or “she,” I hope you’ll consider switching to “they.” You don’t need to be trans to be called “they” and you don’t have to be nonbinary or gender nonconforming or anything. If being called “they” feels more powerful for you, feels even the slightest bit better, then honey, go for it! There are no rules about who can use neutral pronouns or not. “They” is open to all, and I wish more people would use it.

When it comes to pronouns more generally, we live in a world where conservatives have spun the story into exactly the opposite of what’s true. The stereotype is that trans people are SO PICKY about pronouns. That we are insufferably particular about them. But from every interaction I’ve had in the trans community, the reality is that most of us are very chill about pronouns. It’s okay if you mess up on accident, no biggie! It’s okay if you still struggle with it, so long as you’re trying. We are very patient and understanding and empathetic.

But conservatives? OH MY GODDESS are they specific about their pronouns. I mean have you ever playfully called a Republican heterosexual cisgender man “she” or “girl” casually? Talk about defensive! The truth is that people of all genders can be particular about their pronouns, most especially cisgender people. People who prefer to be called “she” care deeply. People who prefer to be called “they” care deeply. And people who prefer to be called “he” care deeply, too. I mean, what would happen if The New York Times refused to refer to Donald Trump as anything other than “she”? Who’d be picky about pronouns then, huh?

HG: You navigated your dad’s lukewarm reaction to your coming out at age 16 with understanding and grace. And your college entrance essay, about buying and wearing your first pair of high heels, was wise beyond its years. Do you think you had to grow up faster or work harder than your cis peers?

JT: I certainly had to grow up more quickly than others—any kid who’s different has to—but it isn’t because I’m more mature than anyone else. It was a matter of survival. As a feminine child, I had to navigate a daily minefield of gender policing, had to have an acute awareness of social norms, and had to develop skills that would protect me. One of those skills was humor, because if you knew how to be funny, you could get away with being a queer child. Another of those skills was building relationships with adults and charming my teachers. If adults in my community liked me, it meant I’d be more protected when people tried to bully me for my gender.

I also learned to achieve academically and extracurricularly, because that provided yet another layer of safety. I always say that, if I had a boyfriend in high school or had a gender that was socially acceptable to my peers, it would’ve ruined me academically. The only reason I invested in school so heavily was because I was struggling to survive. I look back on my younger self and I’m just like “sheesh, kid, would it kill you to make a B?”

Looking back on it, I wish I didn’t have to grow up so quickly. I wish that I didn’t need to develop social skills or emotional intelligence in order to be protected. I wish that there was nothing to be protected against. All children deserve safety, love, and affirmation. It’s a shame that so few trans and queer kids got that.

HG: In Sissy, you explain that you prefer the metaphor “coming out of our shells” instead of “coming out of the closet.”

JT: I have trouble with the metaphor of “the closet” because it has no origin story. How did queer and trans people get in the closet in the first place? Who put us there? Also, my closet is the best “room” in my house—it’s where all of my dresses and rompers and cute jackets live—so why on Earth would I want to come out of it?

The idea of “coming out of the closet” also isn’t iterative. It sets coming out as a one-time thing, as something that we do once and then never again. And if we don’t come out, somehow, it’s our lack of courage, our lack of audacity that’s to blame. The closet metaphor sucks because it implicitly blames queer people for not coming out.

That’s why I like to talk about myself as a snail. I’m a weird, shiny, gay lil’ vegetarian animal just trying to explore flowers and crawl around my garden in peace. But then the world scared me. So I went into my shell. I hid. And I came out when I was ready, when I felt safe. When a snail recoils into its shell, it’s not the snail’s fault. It’s because you scared it. That’s the reality of the trans and queer experience. We don’t hide for no reason. We hide when we are threatened, and we always reserve the right to go back into our shells—if only temporarily—when we’re scared or treated with aggression.

HG: I imagine that the responsibility of educating people about gender often falls on you. Do you mind doing it?

JT: I am often (read: daily) asked to educate others on gender. That burden can certainly be overwhelming, but more than that, it’s boring. In writing Sissy, I tried to push back against the imperative to “educate,” or at least sought to educate differently. Why does education have to be sanitized? Why do we always center education in our minds, when the much more important education is that of our hearts?

I had incredible creative freedom in crafting Sissy, both in terms of content and in terms of tone. I wrote the book that I wanted to write. There is nothing about this book that is pigeonholed or apologetic. I refuse to do Trans 101 for anyone anymore (that’s what Google is for). I’ve spent far too much of my career doing that already. This book is for readers that want to go simultaneously deeper and far, far more shallow. It’s for people who want devastating truth served up with a side of dick jokes, trans primers be damned. What I love about my editor and my team at Putnam is that they’ve been on board with that from day one. I don’t know how I got so lucky, but I thank the universe every day for it!

HG: How do you describe your personal style? And what role did it play in you discovering your gender identity?

JT: I describe my fashion sense, loosely, as kinky 1980’s grandma chic. I love bold patterns and prints. I adore sequins. I live for vintage clothing of all types (though not all vintage clothing fits me because, honey she has rib cage). My grandmother is my fashion icon.

More generally, fashion has played an integral role in my political development. When I put on a dress, I am putting on a revolution. Wearing garments that are historically understood as “feminine” is a gesture of rebellion, a fuck you in the face of those who seek to suppress the brilliance of human expression. I pay a price for my rebellion. Navigating the world in a dress, the stares and heckling and attention are relentless. People respond to my revolution and are polarized by it. They either join up, cheering me on, or seek to stifle it. The process of learning to wear lipstick for the first time wasn’t “just for fun” or “an experiment.” It represented a lifetime of healing, summoning all of my courage to join the trans revolution that I so desperately needed. Clothing, accessories, and makeup are more political than we ever give them credit for.

HG: What did you learn about yourself while writing Sissy? Did anything surprise you?

JT: Writing this book has been the single most healing thing I’ve ever done in my life—much more so than I’d anticipated. I worried the process of writing the book was going to be painful, that curating my most private thoughts and greatest failures was going to be exhausting, but the beauty about a book is that you can’t phone it in. You have to write from the heart. You have to write the book that is burning inside of you. And the book burning inside of me was, first and foremost, one that I wanted to read.

In many ways, I wrote this book for myself, to make sense of what navigating the world has felt like; to try to stitch my broken heart back together. But the beautiful thing about healing is that it’s contagious. I only learned to heal from my trauma after watching other people in my life do it. As a book, Sissy documents the journey that I’ve undertaken to heal my gender-based trauma. My hope is that it inspires everyone it touches to do the same. I’m trying to be part of a movement of people rising up and claiming that gender has hurt us all, and that we owe it to each other to heal together and in public.

HG: How can cis people be better allies to the trans community?

JT: There are four pivotal things that cis people can do to be better allies.

First, try to approach gender with more chill and a sense of play. We live in a world where gender is so serious, but in an ideal world, it wouldn’t be. In an ideal world, we’d all be chill about gender. Did you misgender someone on accident? It’s okay, just fix it real quick, say a quick sorry, and go back to being chill. Did you catch yourself inadvertently policing someone’s gender expression? Don’t worry, just apologize, try not to do it again, and go back to being chill. Chill is key. Chill is the future of gender for all of us, because in world free from patriarchy, what about gender wouldn’t be chill?

Secondly, try to problematize your own gender. Your gender is more complicated than you give it credit for. What’s been your journey towards your gender identity? How did you know that you were a woman or man? How did you know that that identity fit? When has your gender been policed? Cisgender people have complicated genders too, and the more reflective you can be about your own journey with gender, the better ally you’ll be to the trans community.

Third, raise children differently (if that’s something you ever choose to do!). Gender is learned behavior. If we all taught our kids that trans people are wonderful and that there’s no such thing as a “typical” boy or girl, we’d wipe out transphobia in a generation. Also, don’t be afraid to be honest with your kids about the full complexity of gender. It won’t confuse them; it’ll only help them to see the world as it actually is. You wanna know what’s super confusing and traumatizing for kids? The gender binary. You wanna know what’s easy as pie? Gender diversity.

Lastly, and most importantly, listen to trans people when we tell you what we need. When we say that we need easier access to hormones, help us make it so. When we say that gender should be taken off of all forms of government ID, help us make it so. When we say that all restrooms should be gender neutral and should provide sufficient privacy, help us bring that to fruition. When we say that we feel unsafe in our communities, believe us and help us find ways to build safer communities (while also abolishing prisons and ending police brutality, s’il-vous-plaît).

HG: Should we keep trying to reach people who aren’t listening about gender, or focus our attention on others?

JT: We can’t give up on anyone. We have to keep trying. We owe it to ourselves and to the world not to give up, even when it’s hard. That was something I strived for when writing this book—I was committed to making Sissy accessible to anyone. I wanted to write a trans/queer book that almost anybody could pick up, read, and find joy in. I wanted to write something that spoke plainly enough to resonate across the aisle, but complexly enough to be eye-opening. I am equally invested in my trans and queer siblings loving this book as I am my next-door neighbors from growing up.

As someone who grew up in North Carolina—what many would define as “Middle America”—I refuse to dismiss those who don’t “get” this whole trans thing yet. I refuse to give up on Middle Americans, because I think we’ve underestimated them greatly. People in Middle America, people in the South (where I grew up), people in the Midwest or in flyover states—we are not dumb. We are not uneducated so much as underestimated. If we deem certain trans stories or ideas to be “too complicated for Middle America to understand,” is it any surprise that they don’t understand them? If my life has taught me anything, it’s this: You can’t underestimate people. People can change. People can learn. It just takes a different type of connection, persistence, and superhuman patience.

I’m not sure if this resonates with all readers, but in the metaphorical sense, I am Leslie Knope and Middle America is Ron Swanson (from Parks and Recreation). Like Leslie, I will always wear you down and convince you to support me in the end.

HG: What do you hope people take away from reading Sissy?

JT: I want people to know that there is no such thing as a “correct” gender. All gender is correct. All gender is beautiful. However you choose to express yourself in the world, it’s beautiful. However you choose to relate to your body, it’s correct. We all deserve the right to live in our gender, whatever it is, and be treated with respect, dignity, kindness, and love. It’s a stunningly simple vision that’s astonishingly complicated to actualize.

Also, if Sissy does its job, I hope that people laugh so hard that they pee a little. Or at least snort. I’ll take either.

Sissy: A Coming-of-Gender Story is available wherever books are sold.