I Started My Career As A Woman. Now I'm A Man. Here's What Did & Didn't Change.

Photographed by Mary Beth Koeth.
When I transitioned from female to male back in 1995, a lot of guys at the advertising agency where I worked joked that I had “bigger balls” than they did. While physically that was nowhere near true (that surgery would come later) I got the point they were trying to make, even if it wasn't exactly PC. Changing your gender in front of everyone you know takes a huge amount of courage — especially in the workplace. But I pulled it off rather successfully, and after two years as Kris, spent the next 18 at the same agency as Chris.

Now, that’s not to say that my transition at work was easy. For one thing, in the ‘90s, the word “transgender” didn’t exist. The only word was “transsexual” which had a very negative connotation — and by the way, still does. There was no Transparent, no Orange Is the New Black, and any pop culture references to being transgender (i.e. transsexual) portrayed characters as deviants or serial killers (think Buffalo Bill in The Silence of The Lambs).

I had to change and redefine existing perceptions around being transgender, and educate my coworkers and clients on what it meant. I also had to deal with the logistics of transitioning — things like beginning hormone therapy and negotiating bathroom use. For the first two weeks after I started my transition, I opted not to use any bathrooms in the agency, so people would have time to get used to the idea of me switching to the men’s room. Instead, I would use the unisex bathroom in a nearby cafe. That meant every time I had to use the restroom, I had to take a 14-floor elevator ride and leave the building. I had to find the right surgeon, and endure what would be 28 surgeries (which meant 28 recovery periods), all during what were meant to be biggest growth years of my career.

I did, however, have a few things going for me. I worked at a progressive and accepting company. And my father happened to be the CEO. At the start of my career, this was a tough one to navigate (it's not easy being the boss' daughter, especially when you know deep down that you're his son). Early on, I had to work twice as hard to prove I was at the company on my own merit. But when it came time to transition, it gave me job security. Instead of worrying about being mistreated or fired — a big concern for most of the transgender population — I could focus on developing and executing my transition strategy. With the help of my therapist, I realized that the way I acted could shape how other people reacted. It was effective — but also nearly a full-time job in itself.

I realized that the way I acted could shape how other people reacted. It was effective — but also nearly a full-time job in itself.

As the first person in the agency to ever change genders, I knew I had to set an example. Right from the beginning, I decided I wasn’t going to be meek or secretive or ashamed about my transition. Instead, I was going to be an educator: honest, open, willing to volunteer information and answer questions. I’m an over-sharer to begin with, so this was really an extension of my personality. Another big part of my personality is my sense of humor, and I made sure to use it wherever I could to make people around me comfortable. The last thing I wanted was for my coworkers to avoid me out of fear of saying the wrong thing. So, I made jokes whenever possible, so people would know I wasn’t sensitive about my transition. And over time, the creatives who worked on my team found a huge benefit to my transition: They’d present work to me three or four days after surgery, when they knew I’d be most doped-up on painkillers. God only knows what I approved!

And once all my coworkers got to know me as Chris, my career changed for the better. A lot of people ask if it was because I'd become a man. And the answer is yes. But it's not because I was "a man." It's because I was Chris, the man I'd always meant to be. In meetings, finally comfortable in my own skin, I felt able to speak up. As Kris, I had spent so much energy pretending to be someone I wasn't. Now, I could pour that energy into my work, becoming brighter, funnier, and more engaging. People even told me I looked taller. Some asked if it was the testosterone, others accused me of wearing lifts. Enough people commented that I went home and actually measured myself. Sure enough, I had grown. It took me a minute or two, but I realized why: As a woman, I hated the fact that I had boobs (or what I called “booby prizes”), so I always used to hunch to make them less noticeable. With them gone, I was now standing up straighter and three quarters of an inch taller. Hey, at 5’4” every little bit counts!

I also had new motivation to work my ass off. I wanted to be known for my work, not my gender change. And pushing myself to the max made me study how coworkers I admired got ahead. Their secret? Asking for what they wanted. It was so obvious, but something I'd never felt I had the power to do. But after my transition, I was like, Screw it; I work just as hard as everyone else, and if I feel I deserve something, I'm going to ask for it, too.

Did I get everything I asked for? No, but at least I knew I wasn't holding myself back. I took my reviews and self-evaluations very seriously and asked my managers what it would take for me to get to the next level. Then, at my next review, I’d say, “You told me last year I needed to do XYZ to get promoted. Here’s what I’ve done.” When you lay it out like that, it’s very hard for someone to say no.

As I moved up the ladder and started giving reviews, I was surprised at how few people take this approach. And eventually, over the course of my 20-year career, I worked my way up to executive vice president, group creative director: A damn good accomplishment regardless of gender, but unfortunately an elusive one for many others in the trans community. Workplace discrimination is a real problem. Of transgender employees, 90% report being harassed or mistreated on the job. In the 20-plus years since I've transitioned, much has changed, but there's still a long way to go.

Trans rights in the workplace benefit everyone. Because, as I learned firsthand, in order to have the freedom to work your ass off, you have to start by feeling comfortable in your own skin.

For more on Chris Edwards’ experience transitioning, check out his newly released memoir, BALLS: It Takes Some to Get Some.