17 Signs I Was Transgender But Didn’t Know It

Male-To-Female, In TransitionNatalie Egan
Image by Rebecca Lieberman

Image by Rebecca Lieberman

For 39 years, I did my best to live my life as a man named Nathan Egan and to hit the different markers of “success” that culture had defined for me. I was the Founder & CEO of a fast growing technology company. I worked hard to have all the right academic degrees and build the right networks. I married the most amazing woman and I became the father of three beautiful children. I truly felt like “I had it all” and that I was living the dream.

But there was always something gnawing away at me that I never understood and couldn’t explain. Only now do I understand it as a deep dissatisfaction with myself. This inner misalignment and horrific fear of expressing the person I really was inside. Which was painfully and ironically the opposite of how I presented to the world: as a man.

In retrospect, it all makes sense. My conflict came from my innate need and want to do the things that genetic girls or women get to do. I was transgender.

But I only figured that out about nine months ago, after grappling with a series of life events that led me to finally be able to put a word to this reality that I had been repressing for so long.

Now that I am “out”, I experience a lot of wonderful new emotions and thoughts I have never had before. But sometimes they aren’t quite so fun, like when I get an anxiety that people are angry at me because they think I was tricking them my whole life. But the truth is, I didn’t know I was trans before now. I wasn’t allowed to know, and I certainly wasn’t given permission to explore it. My truth was so deeply repressed, even I couldn’t see it, but looking back, there were signs that seem so obvious to me now.

1. I was obsessed with the song “Lola” by The Kinks.

I remember hearing this song by The Kinks for the first time when I was about six years old and I immediately fell in love with it (yet I had no idea what it meant). And even though I would always sing along to it, I never internalized the lyrics.

For those of you who are unfamiliar, here’s a taste: “Well, I'm not dumb but I can't understand / Why she walk like a woman and talk like a man.” You get my point—though somehow I never figured out the complex gender situation in the lyrics—until now.

2. I thought Playboy was a genuinely interesting magazine (even as a very little kid).

Anyone who knew me growing up knew that I was fascinated with women. I was the first of my friends to think that Playboy was a must-have magazine; I even remember begging my mom to buy me a copy for my 10th birthday! I also secretly wanted to read magazines like Vogue, Cosmopolitan, and any woman’s shopping catalogs that came along.  As a kid, I was relatively shameless about these kinds of things, but my obsession with looking at women made me feel ashamed as I got older.

Why? Because my interest wasn’t just erotic. What I was never able to explain until recently was the confusion in my head between being attracted to a beautiful woman, and wanting to actually be one. As a result, I spent so many years wondering if I was the only guy that felt this way, or if all guys did and no one was willing to talk about it. But it turns out, that like sexual preference, gender identity is also a spectrum.

3. I’ve always loved women’s bathing suits.

Throughout my childhood, I had this problem that whenever I encountered a female bathing suit of my approximate size, I wanted to put it on. And if the circumstance allowed (such as at a family friend’s house), I often did—despite the fear and panic someone would walk in on me. Whenever I did this, I would quickly look at myself in the mirror and then basically rip the suit off before I could get caught.

Doing this truly felt like a compulsion, a need. And yet I never probed why, so the habit remained something I was embarrassed about, and didn’t understand at all.

I also loved looking at other women in bathing suits; I was in awe of their confidence and beauty. But this was more socially acceptable, even though deep down I knew something else was up. I recently admitted all of this to a friend who had already started her transition. She looked me dead in the eye, and said “I know exactly what you are talking about, hon.” It was such a relief.

4. I was repelled by the words “trans,” “tranny,” “transvestite,” and “transgender.”

Throughout my life, I felt these terms were the grossest words I knew in the English language, and hearing any of them always made my stomach twist in knots of disgust.

Of course, I had NO idea what any of these words meant (or what the differences were between them), nor did I understand why I would react with such negativity. What I did know was that I thought they were related to some grotesque deformity of one’s genitalia.

It turns out that being transgender is about identity. Now, I take pride in who I am. I am trans.    

5. I hated girls’ toys (and the color pink) as a kid.

While I was never into GI Joe figures or Matchbox cars, I also don’t identify with the narrative some trans folks tell of loving girls’ toys and other stereotypically feminine things during their childhoods.

In fact, I DETESTED Barbie, jewelry and other small, “girly” trinkets and toys. Of course, now I think I was brainwashing myself to reject girls’ toys so that it wouldn’t even occur to me to identify with them or feel curious about them. It was a successful defense mechanism. I stuck to Lego bricks sand art, which became my creative outlet and one of the few ways I felt I was able to express myself.

6. Spas were always my idea of a good time.

Even as a young child, I was deeply attracted to the idea of beautification and being pampered. When I walked by hair salons, I wanted to be inside with all the other women.

During my adolescence, I convinced my parents to get me a massage, and became addicted (and still am!). I was always surprised that none of my guy friends were into this stuff, but I didn’t press the issue. I just knew that I wanted to have cucumbers on my face and look like the women that were in the advertisements for spa retreats. Obviously, there’s nothing wrong at all with being a guy and loving spa treatments; but for me, given everything else I know, I am now able to read this as one of many signs.

7. I was deeply sensitive on the inside, and hard to get to know on the outside.

I have always been super emotionally intuitive and sensitive. My sensitivity has various manifestations, but I remember getting very emotional and crying for no reason on several occasions in my past. There was also always a latent, baseline level of anxiety that troubled me. I now believe a lot of it stemmed from fear—the idea that if people really knew me, they’d reject me.

At the same time, I was also really hard to get to know. My few closest friends and family knew me as nurturing and socially quite extroverted, but the rest of the world saw me as stoic and guarded. In retrospect, I now understand that I put up these barriers because I didn’t want to be known. To be known, even a little bit, increased the risk of the world figuring out who I really was.

8. I loved looking in the mirror, but avoided being in front of a camera.  

As a kid, my mom used to catch me staring at myself in the mirror, and she would tell me to stop because she thought I was being vain. Vanity wasn’t a fair assessment, as I actually thought I was ugly. And even though I was told that I was handsome, I just wanted to be “pretty.” As a result, I spent hours in front of the mirror trying to figure out my dissatisfaction with my own image. At the same time, I was so jealous of girls and women who got to sit in front of mirrors with the job of making themselves prettier!

Another related sign for me was the fact that I avoided being photographed. I hated pictures of myself. Instead, I was always the photographer (pre-cell-phone-cameras). I was so into photography that I almost pursued it professionally. My strength was portraiture, and I was particularly interested in taking photos of women. I would study their faces for hours in the dark room. It wasn’t sexual, but I did explain it to myself as part of my attraction to females. Now I know that I simply didn’t identify with my own image, and was interested in looking at people whose self-expressions resonated with me far more.

9. I felt that I was born with a secret.

Despite having been deeply repressed for my entire life, I always knew something was different about me. It felt analogous to the deep discomfort and burden of keeping a dark secret. But to make matters worse, I didn’t even know what the secret was. The best I could do to express it was to put words to the following idea: If people know who I really am, they will reject me. This was a horrible thing to grow up with, but now, clearly a sign that I was transgender and didn’t know it.

10. Being pregnant was appealing to me.

When I was younger, I would stuff a pillow in my shirt and pretend that I was pregnant. Looking in a standing mirror, I would try to position myself from a profile perspective so that you couldn’t tell I was just a boy who would never give birth.

Each time my wife got pregnant, I was jealous of her and how her body changed throughout the entire process. There was so much life force bursting from her in the final weeks of each pregnancy! It was a miracle that I wanted to experience firsthand. After our first son was born, she had trouble breastfeeding so I quickly stepped up to the challenge to become her lactation consultant. She was always surprised by how much I wanted to help feed our babies—and so was I—but doing so felt very natural for me.

11. I was able to connect well with women, but not “alpha” women.

I always worked well with women. But every once in awhile, I experienced major conflicts with women in authoritative positions of professional power. In retrospect, I now understand that I was just resentful of their ability to be both feminine and “alpha” even though I internalized my jealousy as pure aversion. Now I respect powerful women in ways I never was able to.

12. My relationship with my daughter was always fraught.

In fact, I think it’s fair to say that my relationship with her was horrible for a period of time, especially in the two years leading up to my recent realization that I am trans. We fought about seemingly everything and when I asked her to do things she would either ignore me or talk back.

Since my transition, it has been amazing at how well we connect. I tell people we are best friends, because we are! We’re incredibly similar, and have all sorts of things we can relate to and talk about.

13. My dad’s “father-son” activities were not my thing.

My dad loves to go hunting and fishing (and so does my sister, ironically). I didn’t enjoy either activity, and would always bring my camera to take nature pictures whenever we would go together.

While we were growing up, my dad would proudly tell this story about how we went to Arkansas to go turkey hunting, and how I saved the day. According to his narrative, the turkeys weren’t coming to the blind, and after several hours of waiting, I had the “genius” idea to make the male turkey call (even though we were trying to call them in with the female call). Upon doing so, the male turkey came barging out to protect his territory, at which point, my dad victoriously shot the bird dead. Over the years this has become a legendary family hunting story my dad proudly tells again and again. Little did he know that every time told the story, my stomach twisted with guilt. I felt like I tricked the turkey. And by hunting, I felt I was tricking everyone.

14. I loved shopping, adored fashion, and crossdressing was becoming a regular thing (even if I couldn’t admit it to myself).

For years and years, I couldn’t accept that I was a crossdresser, even though I was doing it more and more often and my woman’s shoe collection was growing huge.

To me, shopping and dressing was a therapeutic activity, justified to counterbalance the stress of my life as the CEO of startup and the father of 3 little kids. Even if it was just temporary, I was able to escape for little while.

Eventually, I became so familiar with this internal rationalization that I decided it would be how I would explain it to others if I ever got caught: I do it to destress. In hindsight, it’s clear that I was just begging myself to express who I really am.

15. I have a tramp stamp.

Enough said.

Well, it really isn’t a traditional “tramp stamp”, but it is close enough (in the center of my lower back). My friends used to make fun of me for it. But the image always meant the world to me and now represents a big piece of my trans journey, which of course makes me super proud.

16. Shaving my legs for biking was a huge moment for me.

I have always loved serious road biking, but when I first started I felt embarrassed about wearing the really tight clothes and what people might say if I shaved my legs. To make myself feel better, I reminded myself that women did both of these things all the time and owned it. I specifically remember the first time I shaved my legs and it just blew my mind that I hadn’t been doing it my whole life. It felt so right.

17. My wife once flat-out asked me if I was trans.

About two years ago, my wife asked me to watch a an episode of Oprah featuring the journey of a beautiful transgender model named Lea T, which I agreed to do reluctantly. At one of the early commercial breaks she asked me bluntly, “Do you think you’re transgender?”

I was so horrified by her question that I felt physically ill. In the moment, I totally rejected the idea that I was transgender. I rationalized her suspicion in my head, telling myself that I was a crossdresser—anything I was doing was merely female impersonation, an isolated act of creative expression. I got up and left the room, pissed at my wife for even thinking this could be the case.

Of course, this was the biggest and most obvious sign of all.