Simon Aronoff remembers being a child who would go to sleep with an expectation of waking up in a boy’s body, rather than the female one he had. As for the name, Jill, that could be changed a bit more easily. While the physical transformation didn’t took place, Aronff says he always had that identity that leaned toward the male end of the spectrum, even if he didn’t quite know what it meant. So, despite coming out as a lesbian at 15, Aronoff still felt more like a big brother than big sister to his younger sibling, Daniel.

”I taught him how to shave his face and we’ve always played in the dirt and things like that,” says Aronoff. ”I stopped picking on Daniel when he got bigger than me. I’m definitely his little big brother. He’s almost 6 feet tall.”

Though the older Aronoff brother may ring in a couple inches shorter than most men his age, he’s a giant when it comes to advancing transgender equality and other progressive issues. Today, barely 30, he serves as the deputy director of the D.C.-based National Center for Transgender Equality. That’s after helping to found the Transgender Law Center, working on high-profile cases in progressive communications and helping his alma mater, Smith College, progress on transgender issues while maintaining its status as a women’s college. Going to Smith has actually helped Aronoff in non-educational ways, too, he jokes.

”When people ask me where I went to school, they want to know if Smith has gone co-ed,” he says with a laugh. ”That’s one of the big ways that I out myself.”

A bigger way is by being one of today’s most prominent young trans men fighting for equality.

METRO WEEKLY: How long have you been in D.C?

SIMON ARONOFF: It will be two years in August. [My partner] Sarah has been here longer, because she was in law school here before I came out from San Francisco.

MW: Do you consider going to law school?

ARONOFF: People have told me I should, but after being a partner of a law student, watching her study for the California Bar exam, no way. Not even if you gave me a giant scholarship.

MW: I’m surprised to hear you say that, because your résumé is expansive.

ARONOFF: But with fun stuff. [Laughs.] I’ll leave the law school to [Lambda Legal Transgender Rights Project staff attorney] Cole Thayler and [National Center for Lesbian Rights Legal Director] Shannon Minter and those guys.

MW: You recently worked on situation in Florida that was not so much fun: the Largo, Fla., city manager was dismissed after coming out as a trans woman and announcing plans to transition. Were you shocked by the degree of ignorance, of transphobia, exhibited by the Largo City Commission?

ARONOFF: No, it wasn’t shocking to me. What was shocking to me was that other people were surprised by it.

One of the things that we do at the National Center for Transgender Equality is field calls from people who need assistance. A lot of those calls are from people who have faced employment discrimination, from harassment on the job to ”I’m not allowed to use the bathroom in my building,” to firing, or rescinding of job offers when someone’s been outed. And some people have been outed because employers are now required to send an I-9 form into the Social Security Administration. Sometimes name and gender marker are not matching up, so the SSA kicks back a letter to the employer and says, ”Hey, this paperwork you sent in for Simon Aronoff, we have a file for him, but it says ‘Jill.”’

You would think that in certain urban areas you’d be a little safer. But like the Diane Schroer case — that’s here in D.C. — when she said she’d be transitioning, the Library of Congress rescinded its job offer.

MW: Speaking of geography, you grew up in the Deep South, Fayetteville, Ga.

ARONOFF: I went to Fayette County High School from 1991 to 1995. I knew that I was queer like forever and a day, but I started dating someone for the first time when I was 15. But it was not like, ”Hey, we’re holding hands in the hall.” It was people thinking we were best friends and we were sneaking off and going on dates. We were definitely scared. I was the more outgoing one. Maybe I would push for, ”Can we hold hands if we’re at the mall across town?” But then, no way was that going to happen. It was a realistic fear, I think.

MW: Did coming out first as a lesbian better prepare your parents for you later coming to terms with being transgendered?

ARONOFF: It might have helped down the line, but it’s still like, ”How did you not know, people?” [Laughs.] About the only thing that changed in my appearance is my beard. I was a very butch kid. I demanded to shop in the boys’ section in elementary school.

MW: Had you been eying the incredibly progressive Smith College from Fayetteville for a long time?

ARONOFF: Actually, a funny story is that I had read about Smith College in a Rita Mae Brown novel. Her novels are basically how I survived in Fayetteville. She referenced this famous T-shirt that we had at Smith for our centennial: ”A Century of Women on Top.” She writes just a snippet about Smith, and I didn’t know it was a real place. I thought it was some fictional college that she had cooked up. When I found it was real, I immediately set my sights on it and tried to do my damnedest to do well [in school] and escape to Lesbianville, USA.

MW: Did the notion of attending an all-female college give you pause?

ARONOFF: As a lesbian-identified woman at the time, I thought this would be a place where I would have some community. Smith is a wonderful school, but what I and a small handful of other trans and gender-queer-identified people did that first year was incorporate that transgender element into what was their lesbian-bisexual-ally alliance. There was a lot of education that needed to be done around trans issues. An extra layer was being at a women’s college and what did it mean for male-identified students to be there. It wasn’t until five years later that Smith incorporated gender-identity and expression into their non-discrimination policy.

My first and second years, I was there as Jill. I came back [from junior year away at Georgia State University] as Simon, using male pronouns. That’s where my trans activism started, during my senior year at Smith.

MW: But you began developing a trans identity at the end of your sophomore year, right?

ARONOFF: That’s when I started to have language for it. Leslie Feinberg came to speak at Smith. What freaked me out was when he started talking about transgender. I didn’t really know that word. But I left that talk angry. I was angry at Les Feinberg because he had articulated how I felt, and now I had to deal with it. [Laughs.] I picked up Stone Butch Blues. I made plans to come home, where I saw a counselor, a therapist, for the first time. I talked about gender identity for the first time. I would assume, in Fayetteville, I was this therapist’s first trans or questioning client, but she was amazing.

MW: Returning to Smith after the year in Georgia, as Simon rather than Jill, did you face any transphobia?

ARONOFF: Mostly there was a lot of intellectual curiosity. I did have a few instances where people would say that they would not use male pronouns for me. ”That’s crazy! I’m not calling you ‘he.”’ One woman actually called me ”it.” People on rare occasions had a negative view. Mostly it was curiosity about wanting to learn more about transgender issues and to have an intelligent conversation about what it meant for people with a male or masculine identity to be at a women’s college.

One of the favorite messaging things I’ve ever done is ”single sex, many gender,” which was how we described the Smith campus because, in reality, there’s not just lipstick lesbians running around Smith College. There are butch women and gender-fluid women and trans-identified people, too.

MW: Would you feel as comfortable going to Smith today?

ARONOFF: When I was at Smith, you would look at me and not think I was male. I would tell you my name is Simon, and you would say, ”Oh, this is a female person.” But I would have trouble now as someone who has changed all their documentation and presents male going into women’s space. I don’t think that would be an appropriate thing for me to do. I think it would be disrespectful. But I think a trans woman should have every right to go to Smith.

MW: How soon after graduating did you head to San Francisco?

ARONOFF: I stayed [in Massachusetts] for a year [till Sarah graduated]. I actually worked in a restaurant in Amherst. I was cooking in the kitchen with a bunch of frat boys, essentially. There were a few assholes, because there are always going to be a few assholes. But we would work extremely hard and play extremely hard and come to work hung-over and have fun and talk about how the wait staff was stupid. [Laughs.] I think they respected that I was a hard worker and not trying to push any PC agenda on them.

I met my good friend there, Brendan, who is going to be in my wedding on the 27th. He actually drove out with Sarah and me to San Francisco in 2000.

MW: You’re getting married on the 27th? How much can you talk about that?

ARONOFF: Sarah is fine with me talking about it, but the only thing that worries me is that I don’t want to put my marriage at risk. [We’re planning] a legal, opposite-sex marriage. For trans people, marriage any way you slice it is kind of dicey. I guess you can say we’re eloping.

MW: Back to the cross-country road trip, why San Francisco? Did you have jobs waiting?

ARONOFF: We were so crazy. We had no money, we had no jobs. We just decided we were going to San Francisco because it was a fun place to go to. Brendan wanted to be a bike messenger out there. I wanted to go where trans guys were. Sarah thought she could get an NGO job out there. At one time, we had six people living in a one-bedroom apartment in Oakland.

Simon Aronoff

MW: Looking at your career history, it seems you grabbed some important work pretty quickly.

ARONOFF: I knew that I wanted to do activism/advocacy in some respect, and I knew that I’d always enjoyed writing. Advocacy communications seemed like an excellent opportunity, so I just started on the ground floor at an organization called Communication Works, a non-profit, communications-advocacy firm — like a PR firm for the good guys. We had clients in environmentalism, criminal justice, social justice, economic reform. I was lucky.

We merged with Fenton Communications and became their West Coast office. It was a great job.

San Francisco was amazing. There are not just gay people, but there are radical, queer, progressive people, whether they’re LGB or T. It just felt like a real community of cultural, creative types.

MW: It doesn’t sound like Washington.

ARONOFF: There are two political parties in San Francisco: Democrats and the Green Party. Here, you actually have Republicans. [Laughs.]

MW: What has been your professional high point, to date?

ARONOFF: Being able to work at NCTE is what I’m most proud of, but some of the stuff I got to do at Fenton Communications was really amazing. Like, I was one of three people doing the media on the ground at City Hall during the same-sex marriages in San Francisco. That was really amazing.

Then the Angel Raich medical-marijuana case, being able to do a Supreme Court case. I was 27 and I got to do a press conference on the steps of the Supreme Court. I took my client to be on the Bill O’Reilly show. Richard Perle was in the green room. It was weird. I felt like I was in the belly of the beast.

Working with MoveOn was good, too. I was lucky to be in a place where they were doing amazing work and they weren’t afraid to let younger people do that work.

MW: At 30, you’ve had plenty of career high points. But what are you most proud of in your personal life?

ARONOFF: I guess the most personally satisfying thing is being openly trans so other trans men can say, ”Hey, there are trans guys out there doing stuff and that’s cool. Maybe I can do that, too.” That was a big consideration for why I chose to move to San Francisco, that job discrimination we talked about earlier. And I thought that progressive organizations in San Francisco might have less trouble hiring an out trans person.

MW: Are the challenges for trans men much different than those faced by trans women?

ARONOFF: The biggies are the same: employment discrimination, hate violence and general lack of public education/awareness are the same. But there are definitely differences between what trans women and trans men face. Sexism is alive and well in America, in the gay and lesbian community and the trans community.

The female-to-male (FTM) and male-to-female (MTF) communities are starting to come together in political advocacy. But socializing, I think it’s probably similar to the gay-lesbian divide. My first, close MTF friend is [NCTE Executive Director] Mara Keisling. She tells me things that trans women go through that I had no idea about. And I tell her things that trans men go through that she had no idea about.

I think it’s really important to have something in this piece about trans men, because a lot of the face of the movement is trans women. I would like people to know that I’m doing this work, Shannon Minter is doing this work, Cole Thayler is doing this work. Jamison Green, Les Feinberg, Loren Cameron, Dean Spade — there are trans men doing amazing work in the movement. Our friendships certainly exist beyond the work because we have similar shared experiences. We’ll have discussions about the [gender-segregated] Michigan Womyn’s Music Festival, kind of coming from a female history. I’m not going this year, but the Gender Odyssey weekend in Seattle, on the ”transmasculine” spectrum, kicks so much ass it’s amazing.

MW: Beyond gender, looking at sexual orientation, how do you identify?

ARONOFF: I always joke about being the L, the G, the B and the T. I identify as a queer transgender man. I know that this stuff can change and does change over time — at least for some people, for me. So I may have started being a man-hating lesbian, and have ended up being a queer, bisexual-identified trans person.

MW: Have you become the man that you hated?

ARONOFF: No. I have been lucky in that respect. I didn’t become my father. [Laughs.] I think I’m set as a person. I could change, you never know. I feel like earlier in my transition, I was very much more rigid. Like, ”I am a man now,” and if you called me by the wrong pronoun I would totally freak out and hate it and be devastated for the rest of the day. And now, for example, I don’t take hormones anymore. I think I’m more comfortable with the gray area.

MW: Since you’ve stopped taking hormones, which your body must reflect in some way, does that diminish your own sense of male identity?

ARONOFF: No, it doesn’t, strangely enough. Culturally, the ”most improvement needed” category is fascination with surgery and the thought that it’s all about having a sex-change operation, which is wrong on about 5 million different levels. People need to move beyond trans people as surgical things.

You know, you don’t see [gay publications] writing about a gay man based on what he does in the bedroom, or solely as a sexual orientation. He gets to be a person. You still see, on occasion, with trans people a kind over-fascination with their surgical status, not just, ”Here’s a trans person in our community.”

MW: You’re saying that including mention of a trans person’s surgical status would be like identifying a gay man by asking about his history of, say, anal sex?

ARONOFF: Mara likes to say something like that — not publicly, but I find it hilarious. If I can find a nice way to say it…. You never read a story about, ”Will, who had anal sex in 1998,” but you’ll read about ”Simon, a man who underwent a sex change operation from female to male in 1998.”

We’re still trapped in a ”wrong body” mentality, where they can understand transgender people being born in the wrong body, trapped in the wrong body, changing from X to Y. But the nuance of transgender people being complete human beings is that it’s not all about surgery, that we don’t all want surgery, and there’s not just one surgery. It’s about what’s between your ears, not what’s between your legs. It’s your gender identity, your internal sense of being male or female or something other than that.

I don’t ask or talk about other peoples’ surgeries or other peoples’ genitals and what their bodies look like when they’re naked unless they are a potential sexual partner, or if there’s some sort of medical need for me to know. [Laughs.]

The queer media has come a heck of a long way, but when the LGBT media — it’s not the majority of the stories anymore — when someone hasn’t taken the time to read the Associated Press Style Book on how journalists should report on transgender people, or when it’s so clear in a story that there’s been some sloppy editing where a trans woman is referred to as a man and with male pronouns throughout and you’ll read, ”So-and-so changed legal name in 1999” and then continue to use the old name. That’s what’s disappointing: when stories look like an effort hasn’t been made.

MW: Do you think our culture will accept those gray areas in your lifetime?

ARONOFF: I’ve got about 50 years left. I think it will happen in my lifetime. So much has happened already.

The LGBT community is doing excellent. No one in a position of power believes that transgender people hold the movement back at all.

[NCTE] organized a lobby day earlier this year with 130 trans people from 30 states, and had excellent meetings in the Senate and House. It’s hard to make an argument that trans people are doing anything in the movement but helping it progress for all of us. It’s not that you are L, G, B or T. You can be T and L, G. That’s something people forget. ”I’m queer” works in San Francisco. People get that. [Laughs.]

MW: It sounds like you really miss San Francisco. Should we expect you to stick around or not?

ARONOFF: My job is wonderful, so I’m glad that I’m here doing this. But my goal is to be back in San Francisco. I think the work needs to happen here, in D.C. It’s really important that transgender people have a voice on Capitol Hill, and are here with the other national organizations to have a voice at the table. But I definitely prefer the vibe of San Francisco and the West Coast.

MW: What changes could happen here that would convince you to stay? The weather?

ARONOFF: You can’t stop August from happening. [Laughs.] I would like people [here] to be more open about their own gray areas and fluidity. That would be a big one. I would like to see more space for LGBT queer people, progressive people, not just in bars or dance clubs. They have really wonderful performance stuff in San Francisco that’s both creative and political. There would be gay men and drag queens and big dykes, lesbians, trans people of every persuasion. That’s what I miss about San Francisco the most.

I don’t go out that much, but from what I’ve seen, [D.C.] seems more like gay boys are here, gay women go to the Phase or dance at Apex. Trans people have certain groups here and there. But there’s not this sense of celebration and solidarity, where people are coming together and having a good time. If there is, you should tell me and I’ll be there this weekend.

We are right now the closest we’ve ever been to passing federal legislation that would protect LGBT people. Once that happens, in two to five years, maybe even this year, then a lot of NCTE’s initial mission work will be done.

MW: Then you’ll be free to leave?

ARONOFF: When I feel NCTE is sustainable, I’ll feel I’m in a good place about leaving. But I certainly wouldn’t dismiss staying here and filling Mara’s shoes if she should ever go on to have a less stressful job.

For more information about the National Center for Transgender Equality visit www.nctequality.org.