A beautiful mountain vista with a strong woman wearing a trail running vest and dressed to explore her world.

Embracing Authenticity: My Journey Out of the Man Box and into Womanhood

I knew from a young age that I was meant to be a girl. And I knew from a very young age—as early as six or seven—that how I was in my body was not aligned with the image I had of myself in my head. But even at that young age, I felt and understood the pressure of socialized gender norms—especially within my family. I was told men do this, women do this. Those lines began to blur as I got older, but I still occupied the Man Box for most of my life as a way of shielding myself from pain, from ridicule, from confusion.

In service of fitting in, it made sense to act like “one of the boys” as I grew up. That involved getting into sports that I wasn’t truly interested in—basketball, soccer, football, I tried it all. And it was never a very good fit. That male socialization—it just never felt normal on my end. But I felt so much pressure to conform, to lean into delivering the same mean jibes or disparaging comments I heard from my friend’s mouths in locker rooms. I witnessed unhealthy male socialization among my classmates, and I’d parrot it, trying to figure out how I could fit into their social equation. It never felt natural. It never felt like me.

In high school, I got into theater. I watched many of my classmates come out as gay, which led me to question my own identity. I knew I wasn’t attracted to men, but I didn’t have the language to reconcile the feminine feelings that I had. I found glimmers of my true self here and there—in fact, every single Halloween through high school, I would dress as the most realistic version of a girl that I could imagine. As high school drew to a close, I was hearing all of the plans and futures that my classmates were pursuing. I remember thinking that all I wanted was to be a girl—that I was so tired of developing into this young man, and I so desperately craved authenticity in my life. Without the guidance or language to express and validate my own existence, I was driven to try to end my life. It felt like it made more sense to just not exist than to continue moving through the world as a shadow of myself.

When I started college, I came out as a gay man—which, at the time, was what felt like the path of least resistance to start making space for these feminine feelings that I had. When I came out as gay, I was able to start going out as a version of me that looked more like how I felt inside. I was cross-dressing, loosely trying to figure out drag, working on ways to express this inner self—all while forcing myself to be as presenting as a gay male, despite having had no sexual relations or desires towards men.

I was out in the world living a fake life as a gay man until I was 21, which ultimately made my depression and gender dysphoria exponentially worse. I had a second suicide attempt right after my 21st birthday. When I came out of the hospital, I was 125 pounds—malnourished from drugs and drinking and hiding from my true self. I remember thinking in the hospital “I’m going to get clean, I’m going to be the best man that I can be—it’s too hard to harbor these feminine feelings.” When I got home, I purged every stitch of women’s clothing that I owned. I tossed out my wigs. And I fixated on what I could do to conform to my image of what it meant to be a man. That meant going to the gym, getting muscular, having a career, learning how to be a provider. For the next five years after getting out of the hospital, I was the most hyper-masculine version of myself I could imagine. I grew a big beard, put on 50 pounds of muscle, tried to meet ladies and get into the dating life, which was very unsuccessful because it’s impossible to connect with somebody when you’re not showing up as your whole self.

I was surrounded by a community of fellow “gym bros”—this group where I finally felt like I was managing to pass as one of the guys. They’d turn to me for advice—”Bailey, how’d you get so big?” And I’d show them! This is how I lift. This is how I eat. And it felt great, for a time, to finally be accepted.

Shortly before my 26th birthday, the glory of it all evaporated. I looked in the mirror and it seemed like I had it all—the physique that straight women like to go after, the respect of my community. But I still felt impossibly far away from the mental self-image that I’ve always held in my head. That feeling was absolutely devastating. Once I started having those thoughts, I immediately got back into drugs.

It all came to a head after a third suicide attempt later that year. In the wake of that impossibly dark moment, I finally had the language to name my experience. I knew what trans was. I knew you could transition. I knew hormone replacement therapy was an option. And I was out of escape routes. I had done so much to avoid being myself. So that became my new mission—to be the most authentic version of me that I could be.

Early in my transition, there wasn’t a lot of support. There was broad acceptance, but there wasn’t true, fulfilling, connective support. I felt very much alone at that point. There was celebration amongst many of my friends when I came out as trans, because so many of them saw me struggling through mental health issues, eating disorders, drugs, and alcohol. So there was happiness for me around that authenticity. But there were also family and friends that were deeply attached to this version of me that I had built up over a lifetime—that was who they knew me as, and they didn’t want to lose that image of me.

For many people in my life, me coming out as a trans woman was enough for them to part ways. When I started Hormone Replacement Therapy (HRT), I didn’t see my mom and dad for years. I had some friends, but everything felt so monumentally different in my relationships. My friends that were girls were so eager and helpful—showing me how to do makeup, how to move through the world, how to dress. But that excitement came with its own kind of pressure—it was a fire hose of femininity coming my way, and it was too much at the time.

But through the process of losing and finding and reforging relationships—as painful and tumultuous as it was—I found my people. I found role models that helped me understand a more balanced, healthy version of masculinity as I stepped fully into my femininity. I found a chosen family to take me in when my family did not.

Every friendship and connection that I have now—it’s pure, it’s real, it’s authentic, and it’s validated. When you’re being your most authentic self and you’re open to love, just as you are open to disappointment, you start being able to just devote the energy you want to into those friends, into your family, into your community…and it all just hits different.

What is your advice to someone that is struggling with their gender identity?

I would emphatically encourage anyone struggling to seek out a therapist—specifically someone that specializes in gender affirming therapy. There are a lot of complicated feelings that are going on if you’re questioning your gender identity, and that expert perspective is invaluable to help you process them.

What’s been really life-changing for me beyond therapy is to slow down my life—whether it’s through meditation, through walks or hikes, through self-care practice—and really look inward. When you close your eyes, breathe, and focus on yourself—who are you? How do you see you?

We all have a mental image of ourselves. And that authentic mental image that we truly identify with—not the inflated, manipulated version we show to the world, but our truest self—that’s where to start understanding your gender identity. When I was in high school, when I was in my 20s, every time I saw myself in the mirror, I saw this unfulfilled potential. I saw someone who wasn’t me. And ultimately, that’s what gave me the courage to make a shift and live my truth.

For the men that will be looking at this, what do you want them to know?

For all the men out there, I hope you follow the example of my close friend, Ian. I learned what good masculinity looked like by witnessing it in him. He and I lifted together often before my transition, and he was a pillar for me during that hypermasculine period in my early twenties. When I came out to Ian, he was deeply loving and supportive. His response to my coming out was truly life-changing. He told me he loved me, and that he was happy for me. He gave me a huge hug and told me he was ready to support me however I needed it.

I’d ask you to imagine that your best male friend sits you down and lets you in on their deepest secret—that they are a woman. And I want you to ask yourself—do you have it in you to not be phased? To say “I love you. You are my sister.” That was Ian’s response, and it made all the difference in the world.

So, men, I challenge you to do the work. If you’re afraid of the trans community, ask yourself “why?” Sit with that. I urge you to push past that fear and strive to find our shared humanity—to choose understanding and connection. Because we are your sisters. We’re your friends. We’re your family. We’re your cousin. Your neighbor. We have always been here, we always will be here. And we need you in our corner.