Skylar Kergil Opens Up On The Vulnerabilities Of Being Trans

Skylar Kergil is a 25-year-old poet, musician, YouTuber and writer. Skylar is also a transgender man. Back when he started transitioning during his senior year of high school in 2009, he decided to post YouTube videos to see how he was changing over time. Over the years, he’s attracted a following of over 100,000 subscribers and has become a courageous voice in the transgender community. Currently living in Boston with his partner, Kergil writes music and tours around colleges and high schools in the US sharing his story and opening up discussions around transgender issues.

Skylar and I sat down for a chat about the most vulnerable times in his life and how his transition has given his life purpose.

Skylar! Tell me what were you like as a child.

I was all over the place. I was so interested in everything. My mom said in kindergarten I was the one would invite the new or weird kid to my sandbox so they could play and feel included. For my whole life, I’ve always been interested in the “outsiders.”

What’s the biggest misconception people have about you?

I think because I give off an optimistic vibe people put me on a pedestal that says, “Skylar’s always happy. Skylar’s had an easy life.” That’s not necessarily true.

I noticed your optimism when we started talking. You give off such positive energy. What’s an example of a time when things weren’t so great for you?

Right around when I turned 17, the summer before my senior year of high school, I started conveying to my parents the importance of me starting hormone treatment before graduation. I remember the day we decided I could start testosterone. It should have been a happy day, but my mom would not financially support top [chest] surgery. Nor would she support my hormones either, which is why they still felt far away even though I was turning 18.

I went up to my room and punched through my bedroom window until I hit the second layer of glass. The glass shattered, I cut my hands, and I remember going to my mom to tell her, “This is what I just did. This is how angry and upset I am.” The hardest part was I couldn’t talk to my closest friends about my struggle, let alone my parents. I felt alone and ashamed. I thought, what if I were to just kill myself and be reborn a boy?

What was so painful emotionally right when you started to punch your fists through the glass that got you so frustrated?

The fact that I knew how I saw myself, and the person in the mirror was not that person. I knew people were still seeing me as Skylar or Katherine, and they were looking at my chest and thinking, “Oh what a pain that she or he is strapping her chest down.” I constantly had this feeling that the world was not going to see me as I saw myself. These financial and physical barriers felt like a wall I wasn’t going to be able to climb within the next few years.

At that time, how did you see yourself?

I saw myself as a skinny little tree stick of a boy. I always saw myself as a boy and never had the language for it until I was 15 years old.

I felt the most frustrating thing wasn’t that others didn’t see me as I saw myself, but that I didn’t know how to express fully who I was because of this expectation of me being a daughter, sister and woman.

Today, when you look in the mirror, what do you see?

I try to be positive and pick apart the good parts. My face shape has changed, and my hair has thinned a little bit. I like my lips, and these are the lips that will be smiling when maybe I get coffee stains on my teeth at 50. Everything sort of feels like its mine now. I’m not as dissociated from my reflection. I see myself as a whole rather than as parts.

Beyond your appearance, what do you see?

I see and I hear the same person I saw back then. It’s hard to describe. You know that voice that you talk to yourself with? My voice always sounded like how you are hearing it now. It’s always sounded like that. When my voice first dropped into that after 3-6 months on hormones, I had this immediate sensation of “that’s me.”

Wow. So your inner voice as a teenager was reflective of who you’ve grown to become now?

Exactly. It felt like a very God-like experience when my voice matched the voice I had always been hearing in my hand. It was a sort of affirmation that said, “Skylar, I’ve always been here with you. You just weren’t hearing me.” It was beautiful and powerful.

When you look in the mirror now, rather than what you see, what do you feel?

I feel this wholeness and acceptance of the things about my body that I couldn’t control and also the things I’ve worked hard to make a reality. I feel this overwhelming sense of hope about where I’ve been and where I’m going now.

If you were to imagine step outside of your gender identity, what would be left?

Let’s see... A person who is trying to become bigger and gain some muscle because I believe the apocalypse could happen someday. (laughing) So that’s step one. And what would be left is a person who wants to hear people’s stories. A person who has open arms. A caring, nurturing, creative person who is also a goofball.

If you were to realize all your life thus far was full of clues leading up to right now, and those clues reveal to you what you were meant to do, what would it all lead up to?

I feel those clues would lead up to me being a person who is put here to affirm the diversity and uniqueness of the human experience. I’ve always felt a rebel tendency towards challenging the status quo, and a part of me has always been ready to welcome folks who are wondering if they are weird for not fitting in society. I feel my purpose is to remind people that uniqueness is beautiful, and uniqueness unites us. I feel that’s been my purpose since day one.

When you say “challenge the status quo”, what do you mean?

There actually is no status quo. When everyone is like, “Think for a moment outside of the box,” there is no box. If you want to succeed, this idea of a box or a linear path is what keeps people stuck in it. I haven’t met many people who actually exist in this status quo or box as who they are. Most people are sort of one leg out, one leg in, and they make due. For some people, it’s a sense of safety, but for the majority of people it’s really pretend.


The idea of people being “one leg in, one leg out” and not playing full out comes up a lot with clients I coach. Usually, it’s vulnerable for people to step “outside” and choose to be in an unknown that you’re creating. When was a time in your life when you felt most vulnerable?

When I first came out as questioning my gender. I was 15 and first heard the word “transgender” from an acquaintance at a punk show I was playing in. It stuck with me, and I immediately realized I had always been a transgender man. However, I worried that since no one has ever heard me express this, they wouldn’t understand. I decided I need to be vulnerable and let people know I was questioning my gender and that it was going on for a long time.

How did vulnerability show up for you as you started telling people you were questioning your gender identity?

When I was questioning, I was still hiding a bit of myself. It felt vulnerable when people could ask me questions that I didn’t have the answers to. When I came to coming out as a transgender man, I didn’t feel as vulnerable because I knew the definitive answer to that. I felt vulnerable because I was ready to talk about my gender, but other people being uncomfortable about the topic. I felt open and exposed and ready to answer them in my honest opinion. Rather than asking “how do you feel”, I got people telling me “you can’t be a boy because blah, blah, blah.”

On a scale of 1-10, how comfortable do you feel in your skin?

In the past year I’ve jumped from a 1 to a 10, and right now I feel like a 7. For the first time in my life, I feel confident in the majority of my relationships both with my parents and my partner. I know my parents are supportive of me going through this discovery time of figuring out what’s next. Emotionally, I’m still struggling with some things.

Would you be comfortable sharing more about your emotional struggles?

In my relationships, I’ve had a lot of distrust. Whether it’s lying, cheating or backstabbing, I’ve felt a hesitation to get closer to people. I met my current girlfriend about a year ago through online dating, and before I met her I had just been cheated on. It took me a while to accept love from my new girlfriend, my family and my friends. I had built these walls that were so high to the point where I almost felt I would live the rest of my life alone. I started getting this mentality that I can have enough self-love and friendships that I just barely rely on. I didn’t want to have to need something outside of myself. 

Transitioning always engrained that fight into me. I have to fight to be myself and fight to get what I deserve in life. In my relationships where I kept getting beaten down by lies, I felt the only thing I could trust is myself. I realized trusting only myself is not a way I want to live my life. Part of me loves and appreciates when I can rely on others and know they support me. For a long time, I felt I was the only support for myself.

What does trust mean to you?

Knowing that another person will tell me exactly how they feel even if it’s not what I want to hear. I have a coworker who will call me out on my bullshit, but she’ll do it in a way I understand. Trust is telling me I’m wrong in a way that I don’t feel bad about myself. It’s the other person telling me their truth in a way that is not intended to offend me. It’s the ability to rely on another person being honest about their feelings and intentions.

You mentioned the importance of celebrating your 25th birthday this year. Where are you looking to grow this year?

It’s a mix of narrowing down and expanding. Parts of me are hunkering down on immediate goals and parts of me are expanding. I really want to finish the memoir I’m working on. In the long-term, the “expanse” is moving to the west coast and exploring the pace of life there. I also see myself adopting a kitten and obtaining a degree in counseling or leadership coaching. The most rewarding part of my life has not been the people I have mentored, but the people that they have helped. That’s inspired me so much to empower the LGBTQ folks of today to become leaders and live their authentic lives.

(This article is part of a series that highlights courageous LGBT voices in the YouTube community. For other articles in the series, click here.)

(To join our private Facebook community of LGBT Leaders and Changemakers interested in making positive and lasting change in the world, click here.)

(Some of the questions asked in this interview were taken from “88 Eye-Opening Questions To Boost Your Energy”. To download a free copy, click here.)


Frank Macri is a Certified Professional Coach and Trainer who supports members of the LGBT and expat community who desire fulfillment in their relationships and careers. For more resources, go to