How I Built My Sense of Identity After Coming Out

I began working at Bradley & Parker in 1986 and became CEO in 2017. That was just four short months before the May morning when I publicly came out as a transgender person at work. For as long as I could remember, I’d been living with two distinct personas. After my 56th birthday, however, I decided I did not want to go another day without sharing my true identity.

Planning for a smooth transition 

Because I was coming out much later in life, and especially considering the fact that I had an established career, I planned the identity I was hoping to build very carefully. I took around a year to consider how I could transition without blowing up my professional career — or my entire world, for that matter. I definitely did not take the decision lightly. To many, the transition seemed sudden, but I assure you it was not.

When I was confident that I was ready, I sat down to craft an announcement for my staff. I wrote that email in the same way I communicate every issue to team members, associates, and others in general. I find it’s best to be brief and direct, then inject a little humor to lighten the situation. 

After a good number of drafts, I was satisfied with my original announcement. Finally, I ran the message by a few trusted friends and advisers to make sure I hit all the points I needed to cover. The finished email began, “I am writing to tell you about a matter that is essentially personal, but will result in some changes at work. I will be transitioning my gender. You have all known me as Wayne, but tomorrow morning I will arrive to work as Wynne.” I emphasized that I would continue to lead the firm as I had done for over 30 years. I also told my staff that I was likely to be far less distracted when I no longer had to juggle two separate personas.

Making the transition

I can’t say I didn’t have some anxiety after hitting “send.” There were so many unknowns. I had presented as male in this industry for years. This world of corporate insurance isn’t fun and cozy. Many of us are older, and most tend to lean conservative. Coming out in such an environment was terrifying.

When I walked through the front door wearing a woman’s pantsuit, heels, Tiffany earrings, and makeup, I had no idea what reaction to expect. Simply put, I was hoping for acceptance. I didn’t anticipate full understanding of my gender transition, as I think the concept is difficult for many people to grasp. I knew most of my coworkers were unlikely to understand the feelings and thought processes that had led to my decision. But I hoped they would still be able to accept me for who I was.

I prepared myself for every scenario. But when I arrived at work, my coworkers and colleagues greeted me with open arms. They went out of their way to make sure I felt supported.

I experienced almost universal acceptance at our company. I felt welcomed as my authentic self on that first day. In truth, it was quite a remarkable feeling.

Moving forward and building a new sense of identity

When building a new sense of identity at work, I chose to make the transition a quick one. Everyone’s transition is different. Some people transition their outward appearance gradually by making subtle changes to their wardrobe over time. For me, I decided the best thing to do was to “rip the Band-Aid off” and completely change my appearance once I made the announcement. I sent a clear message that there was nothing ambiguous about what I was doing.

Since coming out and sharing who I really am, I feel much more at ease — both at work and out with friends. The decision to come out wasn’t one I made lightly, though. It was one that I thought through and struggled with over the course of a few years. 

The impossibility of dividing my life between two identities finally persuaded me to take the plunge. Mentally, I could compartmentalize the identities I revealed in the workplace and in my personal life. Keeping them separate in the real world proved impossible, though, as my community was just too small. For example, if I went to a restaurant as Wynne on the weekend, the odds were high that someone I worked with would be there, too. Everyone at work would know by Monday, but they wouldn’t hear the news the way I wanted them to hear it. 

Controlling the message was critical. Once I took care of that, coming out and being my authentic self has only benefited my professional life. When I no longer had two personalities to juggle, I could focus exclusively on being me, and remaining effective in my role as CEO. 

This was always who I was; I didn’t take a pill and change everything about myself. The difference is that, instead of covering one persona with a false identity, I was now able to show my authentic self when I walk through the doors each morning.

Preparing for the negative, but focusing on the positive

No matter how well you plan your announcement and craft the message, people will be shocked initially. When someone they’ve known for years as a male is suddenly presenting as female, you have to give them time to adjust. 

Of course, I’ve encountered some negativity. But those reactions have been far outweighed by the majority I experienced. There was some initial concern over bathroom usage, but that was resolved quickly. I was never made to feel uncomfortable, and now it’s totally natural. Although, we did have a few negative comments from the public when news of my transition spread. For instance, we ran into issues with a couple of customers not wanting to do business with someone who was trans, but those reactions were few and far between.

I’m still a fairly optimistic person regarding human nature. Even so, people still surprise me in the best of ways. Because of their strong political leanings, I worried certain people would be unsupportive. But those people lined up alongside my most vocal supporters. If you treat people well and enable them to be their best, you get paid back in return. Then, when you really need them — even when you do something they aren’t quite sure about — they give you the benefit of the doubt. 

I advise anyone in my situation to move forward without delay when they are sure of their path. No matter what we do in life, and no matter what we achieve, the one thing we cannot get more of is time. Looking back, I wish I had mustered the strength to come out and begin my transition sooner. I urge people to consider their options carefully, but not kick the can down the road if they can avoid it.

As with most things in life, a well thought-out plan for coming out is more likely to lead to a smooth execution with favorable results. Still, no matter how much we plan, there are bound to be unexpected twists and turns in the road. You need to be prepared for those surprises. More importantly, you need to know those twists and turns are just a part of life. They don’t mean the path before you is unsound, especially if you know it’s the one you want to take.

This guest post was authored by Wynne Nowland

Wynne Nowland, the CEO of Bradley & Parker, transitioned at age 56. She came out as trans to her entire company in an email—featured in the WSJ. The email said “You’ve all known me as Wayne, but tomorrow morning I will arrive to work as Wynne.”

She was already out to her family and many friends. Coming out at work was her final step to being who she truly was. As one of very few trans CEO’s, Wynne is able to provide unique insight on trans issues and topics as a trans business leader and entrepreneur.

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