I Was 56 When I Came Out to My Company as a Trans Woman

as told to Jacqueline Froeber

June is Pride Month.

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

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

I saw the clock read 8:59. Fifty-nine minutes earlier, I had sent an email to inform my staff that I was going to work for the first time as a woman. I, Wynne, would be at work around 9am.

Talking to my colleagues was the last piece of the puzzle. He had gone through medical transition and legal transition. I told my closest friends and family. Now I was ready to enter my professional life as Wynne. But I was also so anxious I could barely 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, even decades, so it was understandable that people were surprised. Or surprised.

Part of me was worried that coming out would hurt my career. I love my job and worked very hard to get to this place professionally. But I was finally ready to live my life, my whole life, as my authentic self.

For as long as I can remember, I have always been attracted to the female experience. I wanted to play with dolls and the Easy Bake oven. I wanted to look pretty like the girls. I didn’t want to hang out with the boys.

It wasn’t so much that I knew from the age of 4 that I should be a woman, but that I knew something wasn’t right. But I was having a hard time identifying what that was. In my time, no one really knew anything about trans people. Maybe you saw a sensational headline here or there, but we didn’t have access to the kind of information we have now.

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

This realization was like a calming balm for my brain. He wasn’t the only person in the world who felt this way. Just knowing that I wasn’t as screwed as I thought (that there are other people in the same boat) gave me a sense of peace and also lit a fire inside of me.

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

I didn’t necessarily have those answers, but eventually I had my own. In 2015 I began the transition process.

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

I grew up in an Irish Catholic home and was an only child. My father passed away years before I came out, so it was just us in our immediate family. I told him I wanted him to use my preferred name and pronouns. But when he didn’t, I never got mad at her. I had to find her humor. My mother was a product of another era, so I don’t blame her for not understanding. But a year before her death, my aunt, who was also older but much more progressive, said to her, “Eileen, why don’t you understand 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 as soon as possible, but not too soon. I wanted to soften the surprise but also have a presence so people could see me. I was still his colleague. It wasn’t just a few 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 began to return to normal. The nervousness began to disappear.

A lot of my anxiety came from seeing two guys I was pretty close with at work. I wasn’t sure what his reaction was going to be (let’s just say they’re not exactly liberal). But when they saw me, they embraced me with so much love and support. I’m speechless. Surprised. Hopeful.

I was 56 years old when I left. Do I wish I had done it years ago? Sure. Everyone who knows me knows how happy I am. But you won’t be able to go back in time, so don’t waste a minute hiding who you are. People can surprise you. And you will be surprised how happy you can be.

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