I Was the CEO in a Male-Dominated Field When I Came Out to My Company as a Trans Woman

As told to Jacquelyne Froeber

June is Pride Month.

I remember pulling into the parking spot, turning off the car and just sitting there for a minute.

My office is in the suburbs on Long Island, so it’s quiet. It was just me and the nervous click of my French manicure on the steering wheel.

I watched the clock turn to 8:59. Fifty-nine minutes earlier, I’d hit send on an email letting my staff know that I was coming into work for the first time as a woman. I, Wynne, would be at work around 9 a.m.

Coming out to my colleagues was the final piece of the puzzle. I’d gone through the medical transition and the legal transition. I’d told my close friends and family. Now, I was ready to step into my professional life as Wynne. But I was also so anxious I could hardly breathe.

I sent the email because I wanted to give people a little time to process the news before I showed up. I’m the CEO of the company and I’ve worked with many of my colleagues for years — decades even — so it was understandable that people may be surprised. Or shocked.

Part of me was worried that coming out could hurt my career. I love my job and I’d worked so hard to get to this place professionally. But I was finally ready to live my life — all of my life — as my authentic self.

As far back as I can remember, I’ve always been drawn to the female experience. I wanted to play with dolls and the Easy Bake Oven. I wanted to look cute like the girls. I didn’t want to hang with the boys.

It wasn't so much that I knew from the time I was 4 that I should be a female — it was that I knew that something wasn’t right. But I was having a tough time identifying what that was. Nobody really knew anything about trans people back in my era. Maybe you saw a sensational headline here or there, but we didn’t have access to the kind of information we do now.

In my 20s, everything changed. It was the early ’90s and home computers became a thing. When I got one — it was as big as the wall — my whole world opened up. There were a number of trans activists who’d put a lot of information online and I read every word. I started to see how all the pieces of my puzzle fit together.

The realization was like a soothing balm to my brain. I wasn’t the only person in the world that felt this way. Just having the knowledge that I wasn't as screwed up as I thought — that there are other people in the same boat — gave me a sense of peace and also lit a fire within me.

But, as I like to say, it took me a long time to bake, just like one of those Easy Bake ovens. I went through all the fear, anxiety and emotion that most trans people go through. How would coming out affect my life? Are my friends going to be able to understand? Is my mother going to talk to me?

I didn’t necessarily have those answers, but eventually I had mine. In 2015, I started the transitioning process.

Only a few people knew that I was transitioning. The process can take years, so I had time to consider how I wanted to tell the people in my life. And that meant my mother. I knew telling her would be a challenge.

I was raised in an Irish Catholic household and I was an only child. My father passed away years before I came out, so it was just us in our immediate family. I told her I wanted her to use my preferred name and my pronouns. But when she didn’t, I never got mad at her. I had to find the humor in it. My mother was a product of a different time, so I don’t fault her for not understanding. But one year before she passed, my aunt who was also older but much more progressive, said to her, “Eileen, why can’t you get what’s going on? Why are you being so difficult?”

Overall, everyone in my life has been very supportive. I think some of that is in the approach. In situations like my workplace, I wanted to tell people early but not too early. I wanted to take the edge off the surprise but also have a presence so people could see me. I was still their colleague. I wasn’t just some words in an email.

So, in early 2017, I got out of my car, took a deep breath, and walked into work as Wynne. I saw the same familiar faces — supportive faces — and my breathing started to go back to normal. The nervousness started to fall away.

A lot of my anxiety stemmed from seeing two guys I was pretty good friends with at work. I wasn’t sure what their reaction was going to be (let’s just say they’re not exactly liberal). But when they saw me they embraced me with such love and support — I was speechless. Surprised. Hopeful.

I was 56 years old when I came out. Do I wish I’d done it years ago? Sure. Everyone who knows me knows how happy I am. But you can’t get back time so don’t waste a minute hiding who you are. People can surprise you. And you may be surprised how happy you can be.

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