My Transgender Journey

Hi! I’m trans! I’m a woman, who’s transgender. I’m really happy to be trans, but I wasn’t always so happy. I’m writing this on the International Transgender Day of Visibility, 2023. It’s been a journey for me to get to this place, so I figured I’d write a bit to share with you my story in the hopes that this will lead to more understanding of trans people. We’re a super diverse population, so while my story may have echos of others’, it’s is only really mine. I encourage you to get to know other trans folk too and learn about their stories as well!

I was born in Washington DC, and assigned male at birth. My parents gave me a boy’s name and raised me as their son. I later had two sisters join my family, 2 years younger than me, and then another 2 years younger. I was generally a happy kid, but something gnawed at the back of my mind. This something kept me from truly connecting with others, so I tended to be a loner, interested in computers and escapism through fantasy, science fiction, video games, and the early proto-internet of bulletin board systems. When I was 8 I got a buzz cut. In part I thought it was cool at the time, what boys should wear, but when I got it I was horrified. I hid myself for weeks after that. Later I realized this was my first real brush with gender and social expectations around it.

In elementary school I was studious, but in middle school puberty hit me like a train and I became very depressed. I avoided school, I had few friends, and while those friends and I were close, there was always a gap. My grades fell precipitously and I missed making it into the “good” high school in Prince George’s County, MD (Roosevelt). I sunk further into depression when my friends when there and I found myself stuck at a lower quality high school. It turns out Suitland had a strong music program that I ultimately engaged with, and through it I had some pretty amazing experiences, but throughout gender was confusing and complicated. In high school I identified as “androgynous,” not having had words to explain my being transgender. I had long hair and dated people who turned out to be mainly bisexual.

After high school I went to the University of Maryland, studying Computer Science and Music Composition. I was excited about these courses of study, but I was also thrust into a new place where gender expectations were strong. I lived in a boy’s dorm with a male roommate. My first roommate was horrible, but thankfully I was able to find another person who saw life differently and we became friends. Unfortunately my depression was worse than ever before, so I quickly stopped attending class, preferring to lose myself in video games (Diablo 1, you addictive beast). My GPA suffered, and when my second semester GPA was a 0.16, I was asked to leave the university.

I then found jobs in IT, and through work found a disconnection from my gender. I worked hard, focused on tech and learning, and through that found a sort of solace. I found myself in a leadership role quickly, and thinking I needed to look the part, cut my hair short and tried to look more respectable. At this point I entered a long period of denial and hiding from myself. At various times I would get women’s clothing and hide it, dressing in secret to feel comfortable, but ashamed of the behavior. I went through phases of accumulating and purging this stash all the way until I eventually came out. I got married and divorced, then married again. I moved from job to job and state to state. I was happy in a way, but something was wrong, and over time I was growing more and more depressed below the surface.

Eventually, my wife got pregnant with our kid and my depression became deep and overwhelming. I also had an increased need to—what I later discovered was—be myself. My then wife was concerned and asked me to go to therapy. I fought it for another year, but finally I did go. Within three sessions I realized and accepted that I was transgender, and that I needed to transition in order to be happy. I worked out that the trigger of my kid coming into my life was that I wanted to be my whole self to them. I never wanted to lie or hide any part of who I am. I’m so glad now that my kid gets to know me as myself.

When I came out, I was the CTO of Optoro, a company I’d co-founded in Washington DC. I had started hormones in February, 2017, and then in July I came out by writing a letter to staff on a Friday afternoon, sharing who I was, what to expect, and that on Monday they’d meet me. That first day in the office was scary and awkward, but I was excited to finally be myself. Everyone was super warm and welcoming, if a bit confused 😅. Over the next 6 months people grew to understand that I was Jess, even though I still heard my old name and pronouns from time to time. After a time, I began to know that they saw me as a woman, including the downsides, like talking over me in meetings, or demanding more data then they ever had before for my plans and ideas. A double-edged sword, no doubt.

Eventually, in 2019 I decided to move on from Optoro. I’d put my heart and soul into that business for 9 years, but I needed a fresh start with a team who saw me as me from the beginning. I needed space from my old life, and so I took a new job as CTO of Axios. Having a new team who always called me Jess and used my appropriate pronouns (she/her) was amazing. So was the new opportunity and challenge! This fresh start was powerful in that it helped me embrace myself in a way I had struggled with before.

Two years later I joined Amazon, and I’m proud to say that there hasn’t been a day here where I’ve felt that I wasn’t seen as myself. While I believe the tech industry at large is still struggling mightily with equality among underrepresented people (women especially), I don’t feel like my trans status or womanhood has been in question at any point.

My life has progressed a lot since I came out in 2017 - outside of work I got divorced again (turns out my ex was straight.. we’re good friends still though), and remarried! I now live at home with both my wonderful wife and girlfriend. My 8-year-old kid is the most wonderful kid imaginable. I’m happier than ever. Unfortunately my community is under attack every day right now from lawmakers who want to make the lives of others like me harder. I’m disappointed that people don’t understand that being trans is not a choice, it’s simply who we are no matter what we’d prefer, and that by putting up barriers we’re only making our world sadder. I’m hopeful though that stories like this will help build understanding and trust, and lead to a more equitable world over time. If you’d like to help with that, please reach out, there are lots of small and large ways to contribute. And regardless, I hope that you’ve found my story insightful. I’m happy to add more context as well over time - please do feel free to leave questions, I’ll reply as I’m able.

All the best!


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