Challenges and Choices—My Story

January 04, 2022

Born in 1955 and living through Stonewall as a 14 year old watching from Brooklyn, I simply hid in the fear that somehow my true self would be discovered at a time when even the notion of transitioning was unheard of, as there were no role models, no books, no internet and virtually no precedent. It was in fact in many places illegal to “impersonate” another gender. But the need to be your authentic self grows over time until the point that it overpowers your entire being. It was at that point that I realized I must make a choice. I chose to be me, the real me. Several younger close family members passed away around that time and I thought what if that happened to me and I never got the chance to live as the real me? I never wanted to be lying in that hospital bed watching my life energy fade away forever. 

At the age of five I knew I was different, but growing up in the 1950’s there was no information whatsoever available. I ignored the fact that I really didn’t enjoy playing with boy’s toys and so envied the girls with their dress options, their expressive emotions and everything available to them. When my mom went to the corner store, I would raid her closet and play dress up, never understanding why I was compelled to do this. But despite these growing feelings, I did all of the things guys were supposed to do: meet girl, get married, have kids, but was never truly happy because something seemed very missing.

As the Internet came into being, I read a lot and the puzzle began to complete. Being in the advertising industry and traveling quite a bit, about 15 years ago I was assigned a client in San Francisco, the “epicenter of the transgender universe” as I describe it. In those travels I sought out and talked with so many trans women. It hit me like a bolt of lightening one night when I had the powerful epiphany that their stories and feelings were my story and exactly how I felt. 

Once I truly understood, I made my choice and developed a plan that I began to execute in total secret. I read extensively about hormone regimens, ordering from overseas pharmacies, lest charges hit my prescription plan and someone notice. I found laser hair removal and electrolysis experts. I researched plastic surgeons to find one who would be willing and have the expertise to help with breast augmentation. I took one careful stealth step at a time.

As my physical appearance began to slowly change, family, friends and coworkers began to take notice. I just dismissed it and told them it was aging. Losing facial hair was simply a function of getting gray. Appearing to look fatter, since I had to hide the “twins”, was a function of eating too much etc. I had excuses for just about everything. Once in a while someone would actually volunteer a reason before I answered, and if it was better than mine I continued to use it! 

It was a challenging journey, but when I traveled I would take two bags: a tiny one for the male me and a giant one for Angie. Because we could never have enough shoes! It was really hard living two distinct lives, but Angie had ways of making so many new friends by embracing from the heart. True friends that I still have today many years later. 

Around that time my marriage was also dissolving for other reasons and I was told to go live somewhere else. Knowing that it was over, I put my plan forward in earnest. I began to tell some of my local friends and my best friend. Many decided to unfriend me and tell me I was crazy and not to come back to them until I figured myself out. I told them I did figure myself out and that’s why I’m telling them. Many I lost forever. 

The last major piece was the workplace and I waited because I was quite high up in senior management and many contracts were a result of my clients embracing me and my team. I was concerned that I did not want any of these clients to fire us because they thought I was crazy. I couldn’t live with myself if I had been so selfish and put my team out of work, not to mention the hardship on their families. My biggest client was in North Carolina, the home of the bathroom bills. In a strange twist of fate, my boss, who was the chairman of the company, essentially demanded I “come out” to this client over the phone, something I could not do. I needed an ally at that client to help me and we did it. They threw me a party instead of throwing us out. I told my other clients myself and they were happy for me, as was my team back at my company.

Now with that part behind me and virtually everyone knowing, there was yet one last person I had to tell: my 90-year-old mother. It just so happened that my nephew was getting married and I had no appropriate male clothes anymore to wear and everyone else knew already. So I had to tell her. Her reaction: “OK”. I said OK? She asked me if I was happy. I said yes. She said “OK”. She even asked me what name I wanted to use, because the name she gave me at birth 60 years prior didn’t really work anymore. The moral of that story is that the people that you fear the most, sometimes become your greatest allies and supporters. 

But it wasn’t all perfect. I was assaulted walking along the street early in the transition and wound up in the ER overnight. This guy decided he didn’t like the way I looked, yelled and then hit me on the back of the head with a beer bottle splitting open my head. But I survived and learned I’m not as immortal as I once thought. 

I was frequently pulled aside by TSA because obviously I had something under my shirt and tie. I used all of those personal searches as “teaching moments”. I simply asked the female TSA agents doing the private screening if they wanted to see what was under my shirt. They were all respectful and I will say it was so much fun watching the expressions on their faces when I unbuttoned my shirt, flinging back my tie and exposing my 38 DDDDD “twins”. The same question came up many times: “Where did you get them done?” So much so, that I carried my plastic surgeon’s card with me. 

After finally being my full authentic self to the world, the happiness is infectious and in fact I believe a fountain of youth. When I look at myself over 10 years ago compared to today, I actually look younger and certainly happier. I have engaged in civic life, lecture on many topics, including history, my passion, and so much more. So now it’s time for me to give back for a wonderful life and empower and inspire others with my own story.

View other Monica Roberts Essay Contest Winners from 2021.

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