From sports-loving tomboy, to Boston pride parades, to finding his community online

“Hey, hi, how are you?” the scruffy-bearded guy says into the camera. He gives a friendly wave and a smile, and upbeat music begins to play as the name skylarkeleven appears against a background of a sun and birds.  

This is the YouTube channel of Skylar Kergil: musician, artist, local Boston resident, goer-of-hip-coffee-shops, and transgender activist. Skylar, or Sky, has been making YouTube videos documenting his transition from female to male since 2009. Through the intimate ups and downs of being a trans youth, he’s grown a community of over 115,000 followers who comment and like as he explores his path to understanding his gender identity.

Now, he’s opening up in a new way: with his memoir Before I Had the Words released Sept 5. The memoir drops readers into Sky’s mind from being a sports-loving tomboy to sneaking away to rainy Boston pride parades to finding his community online. He’ll talk about Before I Had the Words at the Brookline Booksmith on Sept 19 at 7 pm.

Beforehand, he sat down with DigBoston to talk petting cats and coming out as a meat eater. Well, among a few other things.

It might be simpler for you to go through your transition without telling your story to the whole world through YouTube and now your book. Why put yourself out there?

I’ve gone back and forth with how open I’ve been, based on how comfortable I am both with myself and with this world. When I first started making YouTube videos in 2009, it was because it had taken me 15 years to meet somebody who was transgender, to hear that word. The life that word gave to me, and realizing that I wasn’t alone, meant so much to me. I don’t know what I would have done had I not met another transgender person who was open about it.

I realized I had the option of keeping it all to myself, transitioning to the man that I am now. But I just found it was very necessary for me to be open because if everyone were to do that, and some people do and that’s totally fine, but if everyone were “stealth,” I don’t know that I would have met another transgender person. I don’t know where I would have ended up. It’s kind of giving back to my younger self.

As a YouTuber and generally as a millennial, it seems the internet has been a big influence on your life and your transition.

If you think about 1 in 30,000 people being trans, we’re pretty few and far between. So the internet has been a pretty essential part of finding community and resources … I think the internet has brought a lot of us closer together, and in the transgender community, the internet is such a life-saving force. There’s so much out there: forums and blogs and Facebook groups for people with all different types of identities where you can have conversations that maybe you can’t have with your friends or maybe you can find information that you can’t get from your community locally.

There’s way more out there now than when I was coming out. Back then, there were maybe three pages I’d go to and two YouTubers. Which was a big part of why I wanted to put my story on YouTube.

On the flipside, people on the internet can be incredibly cruel. Do you read your YouTube comments? How do you cope after you’ve read them?

Hmm… Negative YouTube comments are few and far between now, only because I have a following that will litter me with happy and excited comments. I hardly ever see negative comments. But when I do, it’s hard. I do read them. I think it’s important to see what other people might be seeing.

I don’t want to grow thick skin and say that things don’t bother me and just get over it. But I try to read them and move on. Sometimes I take a break from the internet. Most noticeably, sometimes if I’m feeling really vulnerable, I take a break from publishing YouTube videos and then I get back on there. It’s a helpful thing [the internet], but sometimes I need a break. And everyone is super supportive when I come back and I’m like, “No, it’s okay, I’ve just been petting cats, it’s all good.”

Have you felt differently about coming out with your memoir when so many things affecting trans rights have happened since the election?

I have definitely noticed a change, I think, both with observing others and with my own self. A decrease in hope.

Knowing trans youth who out of high school were planning on joining the military … It was the only way they were going to be able to get away from their parents who were unsupportive and be able to do that for some years—transition, go to college, live their lives, and feel supported, and now that’s off the table. Thinking about those thousands of youths who were going to start their lives that way, seeing that it might not be possible, those are tangible degrees of hope and optimism being removed.

But simultaneously, I guess we got complacent before. There has been a lot of solidarity now. There are many minority groups being attacked, so I think it’s bringing us together in some ways.

Your memoir is even more intimate than your YouTube videos. What’s it like to put this out there, not just to to the world, but also to the people who are in the book?

There are some people in my book who are not portrayed as kind people. Because they were not kind people. They all have pseudonyms. I can’t paint everybody as a good person, but I can’t always paint myself as a good person. It was really hard to balance.

It’s also very nerve-wracking to share thoughts and feelings in written form. Books changed my life. To create something like this and navigate the emotional roller coaster of what to put in … like, do I even talk about why I started eating meat again? It’s like it’s harder to come out as a meat eater than to come out as trans.

It’s a relief, but at the same time it’s scary because my story is out there and it’s not going anywhere now, because it’s in book form. I just hope it informs and inspires others to be their true selves or to write and share their own stories.

SKYLAR KERGIL: BEFORE I HAD THE WORDS. TUES 9.19. 7PM/FREE/ALL AGES. BROOKLINE BOOKSMITH, 279 HARVARD ST., BROOKLINE. BROOKLINEBOOKSMITH.COM