Interview with Sherilyn Connelly

Sherilyn Connelly is a San Francisco-based transgender writer, film critic, and cultural commentator. She is the author of Malediction and Pee Play, an excerpt from her memoir Bottomfeeder, and her writing has been featured in the acclaimed anthology The Collection: Short Fiction from the Transgender Vanguard (Topside Press). Sherilyn’s stories, including The Last Dog and Pony Show and Sherilyn’s Skool for Girlz, explore identity, emotion, and pop culture with incisive wit and deeply personal insight. In addition to her literary work, she writes about film and television for Medialoper and the Gawker Media blog io9, and serves as the head film critic for SF Weekly. Her critical writing has also appeared in The Village Voice.

 

A lifelong lover of libraries, she is pursuing a Master of Library and Information Science with the goal of becoming an archivist. Sherilyn began her gender transition at age 25 and has written candidly about her journey and the cultural challenges trans women face, both in media portrayals and real life. Fiercely independent and refreshingly self-aware, she describes her political action as simply being herself, “largely without compromise.” Sherilyn continues to write, critique, and archive, driven by curiosity, resilience, and a dry sense of humor she never leaves at home.

 

Monika: Hello Sherilyn! It’s such a pleasure to have you here.

Sherilyn: Hi Monika! Thanks so much for having me. I'm thrilled to be part of your blog and to share a bit of my story with your readers, hopefully without boring anyone too badly!

Monika: Could you tell us a little more about yourself? What should we know about the woman behind the words?

Sherilyn: I'm a San Francisco-based writer. Most of my personal writing has been memoir, but over the past few years, I've been working professionally as a film critic and journalist for The Village Voice and SF Weekly. I love exploring how culture reflects our deeper selves, and film has always been a powerful lens for that.

 

"Sherilyn Connelly speaks at Working for
the Weakened" (YouTube)

 

Monika: When did your journey as a writer begin? Was there a specific moment or inspiration that sparked your passion for storytelling?

Sherilyn: I'd always wanted to be a writer from a young age. Two things I wanted to be, actually, were a writer and a girl. At the time, the chances of either happening, let alone both, seemed impossibly remote. Writing became a way to explore and express parts of myself I couldn’t share openly. It gave me a sense of purpose and clarity during years when so much else felt uncertain. 

Monika: Could you tell us a bit more about Malediction and Pee Play? What inspired this particular piece, and how does it fit into your broader body of work?

Sherilyn: It's an excerpt from my first memoir, Bottomfeeder. The piece stands on its own, but in the context of the memoir, it’s part of a larger narrative about identity, trauma, and survival.
Monika: You’re also the author of several other stories, including The Last Dog and Pony Show, The Big Reveal, In the Shadow of the Valley, Outlet, Sherilyn’s Skool for Girlz, and Two-Sixteen-Ought-Four. Which of these stories are you particularly proud of, and why?

Sherilyn: The Last Dog and Pony Show, which was published in the British anthology Unthology No. 1. It kind of sums up a lot about me. I'm also especially proud of the fact that I recently wrote my first feature story for SF Weekly, a 3,000-word article that got my name on the cover and had nothing whatsoever to do with me and/or transgender issues. It felt incredibly validating to be recognized for my work without it being framed solely by my gender identity. That piece allowed me to stretch myself journalistically and tackle a subject I was passionate about in a broader cultural context.

Monika: When you create transgender characters in your books or projects, do you incorporate any autobiographical elements into their lives or stories?

Sherilyn: To date, I haven't actually written any fiction involving transgender people, or really much fiction at all; all my narrative writing has been memoirs. I'm not sure I could write a fictional trans character that was sufficiently different from myself. It would be a challenge not to fall into the trap of making them a thinly veiled version of me. That said, I’ve often thought about exploring fiction more deeply in the future, and if I do, I’m sure elements of my own experience would find their way in somehow.

At Everfree Northwest, 2012.

Monika: Do you think there is such a thing as transgender literature?

Sherilyn: It's part of the broader genre of queer literature, but like everything else regarding trans issues in the broader queer culture, it's not as accepted or taken as seriously. There's often a sense that trans narratives are sidelined or tokenized, even within queer publishing spaces. Still, the body of work by trans authors is growing, and with it, the recognition that trans literature is a vibrant and essential part of contemporary storytelling.

Monika: As a film critic, what is your perspective on how transgender stories or characters have been portrayed so far in art, films, books, and other media?

Sherilyn: I usually cringe when a trans character is introduced in a movie; more often than not, we're still treated as a joke, as an excuse for a cheap punchline. As such, when a trans character is actually treated with a modicum of respect, I make a point of mentioning it in my review. There has definitely been some progress in recent years, but harmful stereotypes and misunderstandings remain far too common. I hope to see more nuanced and authentic portrayals that reflect the real diversity of trans experiences.

Monika: Some critics argue that contemporary art, especially in film, doesn’t offer enough opportunities for women to showcase their talents or tell stories that truly resonate with female audiences. Would you agree with this view?

Sherilyn: Oh, absolutely. Certainly, as far as movies go, the majority of them are still targeted toward men, and in 2013 in particular, there was an astonishing number of films that basically served as the screenwriter working out his daddy issues, with female characters typically just getting in the way. That said, I do think things are slowly getting better. There’s more awareness now about the importance of female-driven stories and diverse perspectives. Independent films and streaming platforms are also helping to create space for women’s voices to be heard more clearly.

Monika: What does it mean to you personally to be a transgender writer? How does your identity influence your work, if at all?

Sherilyn: In my case, it just means I’m a transgender person who happens to be a writer; not everything I write is about being transgender. If being transgender has hurt my career, I haven’t really noticed it. Indeed, I think it’s actually helped me get into a few non-transgender books I might not have been included in otherwise. Of course, being transgender shapes my perspective and voice, even when the subject isn’t explicitly about gender. It gives me a unique lens through which I approach storytelling and critique.

Monika: Are you currently working on any new books or projects? Could you tell us a bit about what’s keeping you busy these days?

Sherilyn: I have two different books in the works, and of course, my ongoing film critic job, which takes up quite a lot of my time. I’m also in grad school pursuing a Master of Library and Information Science with the goal of becoming an archivist, so that keeps me busy as well. Balancing writing, critiquing films, and studying can be challenging, but I find it all very rewarding. Each of these pursuits feeds into the other, enriching my understanding of storytelling and cultural history.

In a natural habitat, 2011.

Monika: There are more and more talented and prolific transgender writers, just to mention a few: Jan Morris from the United Kingdom, Josephine Emery from Australia, and Aleshia Brevard from the USA, as well as a new wave of writers like Julia Serano, Ryka Aoki, Red Durkin, and Imogen Binnie. Do you think there’s a real chance for transgender writers to gain a more prominent status in the literary world?

Sherilyn: Oh, without a doubt. There's always a hierarchy in every subculture, some people who are higher up on the ladder and some who are lower, and those who are higher up generally have a better chance of finding some degree of acceptance and status from the wider culture. As more trans writers emerge and find audiences, I think that prominence will grow. The visibility and recognition are already shifting, and that creates more space for varied trans voices to be heard and valued.

Monika: In general, what do you think about the situation of transgender women in American society today?

Sherilyn: Better than it was when I started transitioning in 1998, that’s for sure. There's still a lot of fear and backlash from conservative and religious circles, but I can't help but envy the younger kids who are just starting out; from what I can see, they have a much stronger support system than existed in my day, largely thanks to the internet. The nascent World Wide Web of the mid-90s was an invaluable help to me in my own coming-out process. Today’s resources, online communities, educational content, and visibility in media, make it much easier to feel seen and supported. That kind of access would have meant the world to so many of us back then.

Monika: Are you active in politics? Do you participate in any lobbying campaigns? Do you think transgender women can make a difference in politics?

Sherilyn: Transgender women can and do make a difference in politics, and I respect the hell out of those who do, but I am not personally involved in politics. I sort of consider my political action to be just being who I am, largely without compromise. Sometimes simply existing visibly as a trans woman in public spaces is its own form of activism. That said, I try to stay informed and support causes and candidates who align with my values.

Knifing, 2004.

Monika: American politics is based on the interaction between different interest groups that seek to pursue their specific goals. How successful is the transgender community in this respect?

Sherilyn: I genuinely believe our biggest obstacle right now is compassion fatigue. The public and the government have come to accept gays and lesbians to a great (and wonderful) extent, and open homophobia is much more difficult to get away with. However, extending that acceptance to transgender people, and, more importantly, understanding that we're not simply a variation on garden-variety homosexuality, and getting them to take us seriously, is proving to be a bridge too far. The attitude seems to be, "Fine, fine, queers can get married and teach our kids or whatever, but now you want us to let a man in a dress use the women's bathroom?"

Monika: What do you think makes the transgender community especially vulnerable to political resistance or cultural backlash?

Sherilyn: The cognitive dissonance that middle America was able to overcome regarding homosexuality has taken a lot out of them, and it's just easier to continue not taking transgender people seriously, particularly on a policy level. It's why the conservatives are fighting so hard to battle pro-trans legislation, and with the kind of ferocity they used to use to battle gay rights. They've given up on the anti-gay positions by and large, but they're nowhere near ready to give up their anti-trans stance, especially because, visually, we're harder to deal with. At least your average homosexual looks normal to them, y'know? But trans people, especially trans women, are easy to use to scare people because we don't look "right" to them, and the gay establishment, having achieved so much of what they've been working for, is reluctant to help us out. Bleargh. (And, in spite of all that, I swear I'm not political!) Still, I think progress will come, just more slowly than we hoped. Visibility is growing, and the next generation seems more willing to see us as part of the broader human picture.

Monika: When did you begin your transition, and what was that journey like for you emotionally and practically? Were there any particular challenges you faced early on?

Sherilyn: I was 25, my very first appointment with my therapist, the twelve-week session that led to me starting on hormones, was on my 25th birthday, and it wasn't easy, though I know a lot of people who had a much more difficult time of it than I did. The most difficult part might have been overcoming all the relentlessly negative images I'd seen growing up of trans women. It helped that I had a job in the tech industry in those days, which allowed me to pay for electrolysis and hormones, a job I got laid off from in 2001, and that I lived in San Francisco. My family and friends were all very supportive, thank goodness. Having that support system made the emotional challenges of transition a little more bearable. I know many trans people don’t have that kind of safety net, so I never take it for granted.

Preparing for anything, 2006.

Monika: When you began your transition, were there any transgender role models who inspired or guided you? How much did you already know about being transgender back then?

Sherilyn: I don't know that I had any role models per se, though I admired Candy Darling on an aesthetic level. I actually knew quite a lot about transgenderism, as I'd spent a lot of time as a teenager at the library, reading everything I could find on the subject. This was long before I found the courage to actually come out, though.

Monika: Looking back, what would you say was the most emotionally challenging part of coming out as transgender? Was there a particular moment or situation that made it especially difficult for you?

Sherilyn: It coincided with breaking up with my girlfriend, whom I'd been with for eight and a half years. We'd been together since we were teenagers and were bound to break up anyway, but it just made starting my transition that much more emotionally tricky. There was a deep sense of loss, not just of the relationship but of a version of my life I had always known. Starting something as monumental as transitioning while dealing with heartbreak was overwhelming, but ultimately, it taught me how resilient I could be.

Monika: How do you view love and relationships in your life? Do you see yourself ever getting married or building a family, or do you find fulfillment in other ways?

Sherilyn: Love is important to me, but I have no intention of getting married or starting a family. That's not for me. I’ve always valued emotional connection and intimacy, but I don't believe those things need to follow a traditional path. At this point in my life, I’m more focused on personal growth and meaningful friendships.

Monika: Personal stories can be incredibly powerful, especially when told by transgender women navigating their own journeys. Have you ever considered writing a memoir to share your experiences more directly with others?

Sherilyn: Heh. That’s practically all I’ve written thus far. I’ve mined my own experiences heavily in my writing, sometimes directly and sometimes through fiction. It’s a way of processing life and maybe helping others feel less alone.

On the Bridge, 2010.

Monika: Looking back on your own journey, what advice would you give to transgender women who are currently struggling with gender dysphoria and feeling uncertain about their next steps?

Sherilyn: Take the plunge. Do what you need to do to be comfortable in your own skin. It's not always easy, but the peace that comes from authenticity is worth the effort. You deserve to live a life that feels true to who you are.

Monika: What are your current goals, and where do you envision yourself professionally and personally over the next five to seven years?

Sherilyn: Oh, good heavens, I could no more guess where I'll be in 5–7 years than I could have guessed 5–7 years ago where I'd be now! Mostly, I hope that I'm making a comfortable living as a writer, an archivist, or preferably both. I’ve learned that life has a way of surprising you, so I try to stay open to unexpected opportunities. As long as I'm doing meaningful work and staying true to myself, I’ll consider that a success.

Monika: Would you say that you are a happy woman now??

Sherilyn: I am, indeed. I've become who I wanted to be, who I truly am. It’s been a long journey, but embracing my authentic self has brought me peace and fulfillment. Happiness, for me, now means living honestly and surrounded by people who accept me for exactly who I am.

Monika: Sherilyn, thank you for the interview!

All the photos: courtesy of Sherilyn Connelly.

© 2014 - Monika Kowalska

  

Other publications about Sherilyn Connelly:

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