Photo by Ana Nichita on Unsplash

He Wore Lipstick to the Office

LA Rysk
7 min readNov 20, 2022

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Who Are We to Judge?

It was 2004. Times were different. It was before the trans awakening. It was before #MeToo. It was before BLM. Fresh out of college, I took a temp-to-perm position and got lucky. At 24, I was assigned to one of the most renowned firms in the world. It was located in the heart of Washington, DC’s business district in a neighborhood known as Dupont Circle.

The offices on the perimeter of the building which lined the street, were inhabited mainly by wealthy men from all corners of the globe; Australia, New York City, London, South America, and South Africa. They were left to make their society-altering decisions in dimly lit spaces behind French doors with privacy-glazed, soundproof glass framed in expensive mahogany. Save for a radiator; their office walls were constructed of ceiling to floor glass, with phenomenal views of the District of Columbia.

These spaces were reserved for movers and shakers of the world, the firm’s partners.

Because of my assigned role, I worked directly with partners. After only a few interactions, I noticed that these men did not gain access to their positions due to privilege or nepotism. None of the men occupying these spaces had mediocre intellect, experience, or credentials. They were exceptional humans.

Despite their accomplishments, wealth, and walls adorned with dozens of degrees and certifications, they were not arrogant. They were very pleasant to me and each other. I was never regarded as less than. I was given meaningful work and mentored without asking. They did not condescend to or demean those in lower positions (at least not outwardly). Many had a welcoming sense of humor and a clever disposition.

Tucked away, in the belly of the building, were the offices of senior to middle managers. Ironically, the optics of these offices were the polar opposite of leadership. Instead of facing outside the building, the ceiling to floor glass was installed at the entry to their brightly lit offices. There were no windows or frosted, soundproof doors for privacy. If not onsite with clients, they sat, heads down, 12–15 hours per day, crunching away at spreadsheets and writing briefs. Anyone walking the halls could see and hear precisely what they were doing at all times. Watching them work was akin to seeing an animal in a zoo display.

I developed surface-level relationships in the first few months and committed first names to memory. One man who stood out, in particular, was *John. (Name changed for privacy.)

John was different from the others. John was about 5'11" with broad shoulders and a stalky frame. He had dark brown hair and eyes. He wore expensive wool and silk blend suits to the office, just as the others, so he fit in that way. Albeit expensive, he wore the same suit often.

He was always pleasant, but a conflicted, tortured spirit eminated beyond his surface. He seemed uncomfortable, even depressed, at all times. His was the type of energy that simply looking into his eyes made you feel downtrodden.

Upon closer look, I noticed a deep scar on John’s face which spanned from the corner of his mouth to his ear. The scar was about 7 inches long. It was not a fresh wound. It was healed, but deep and wide, similar to the split in an over-boiled frank. This was not the type of scar one gets from a slip and fall or an accident. It was not a birthmark. This scar was intentional.

Someone cut John’s face open with a knife.

The sight was familiar but unexpected in that type of environment. In my culture, we refer to this as a “buck 50” in others it is known as a “Glasgow smile” or a “Chelsea smile.” A buck fifty is a scar that requires at least one hundred (buck) fifty stitches.

In the doorway to John’s office was the badge of the military branch for which he served. I connected the dots and gathered that John was injured in combat and never spoke with him about it. I imagined it was a private, painful, traumatic experience and none of our concern. He was here to do a job, and that job was all that mattered.

I wanted to connect with him to be friendly, until one day, noticed John’s office was dark. For a few days, it was unoccupied. Days turned into weeks, and weeks into a month. Due to his sad disposition, I began to worry that perhaps he hurt himself. I asked others where he was and if he was okay and was met with lowered heads, downturned eyes, and tight lips.

I wondered if John had passed away and how it happened.

I beat myself up thinking that I could have been kinder. I could have built a friendship that helped bring happiness to him. As time passed, I became used to his absence and wondered what had happened, but with no answers, moved on.

Months later, I stood in line at a corporate event. Lunch was catered. I grabbed a spoon to scoop the entree onto my plate and felt a tap on my shoulder from behind. It was him.

I smiled. I was elated to see that John was alive! He changed. The discomfort in his disposition was gone. There were no traces of the inner torture. There was peace in his eyes. His spirit was glowing. For the first time since we met, John seemed genuinely happy.

He changed in more ways than this. John wore his standard wool and silk pantsuit and oxford collar shirt. His dark brown mustache was neatly trimmed, but his voice was higher in pitch, and he wore fire engine, bright red lipstick.

I let out a chuckle from disbelief. I waited for John to explain the lipstick. None of the other men wore lipstick. I needed clarification. I waited in silence as I held up the line. I even looked at one of my teammates and chuckled again to see if she would join in or explain what was happening. Why was John in makeup?

I waited and waited. John did not explain. He looked deep into my eyes with the expression of the man in the photo of this article. He was waiting for me.

John was waiting for me to realize he had gone through a transition.

But I could not comprehend what I was seeing. It was 2004. It was before the trans social awakening. It was before #MeToo. It was before BLM. It was before the mass movement of social consciousness and enlightenment. In 2004, there was no delineation of pronouns, open gender debates, and “men” did not wear lipstick to the office.

I searched for an answer. Was John performing? Was this real?

My co-worker shot an angry stare my way with a grim facial expression. She was not amused. It was not an act. This is when I realized what was happening.

This brave soldier, a human with a buck 50, who put their life on the line to protect me and you was depressed because he was fighting against his true self all his life.

He showed up that day in front of thousands of people to let the world know who he was. I am not certain that his gender designation or position was even a protected category at the time. However, he risked it all to be his true self at a time when it was not common or accepted.

John showed up to the office in lipstick.

He showed me how to be brave. He showed me what self-esteem is. He showed me what it means to be fearless and unapologetic in living your life’s purpose at a time when it may not be popular or accepted.

My exchange with John only took about 30 seconds, but to this day, 18 years later, I sometimes shed a tear at my reaction. I regret my response. I regret the nervous laugh. I should have been accepting. I should have hugged John with open arms and congratulated him. I did not understand what was happening because I never saw it before. Now that I have seen it, I cannot unsee it — the experience.

Many people are fighting private battles, being unhappy to their core because they are pretending to be someone they are, not just to please everyone else.

These people can be relatives, sisters, brothers, parents, co-workers, or strangers in passing. If you see someone who looks or behaves in ways that do not conform to what you are used to, who are we to judge? Who are we to think anyone owes us an explanation for not conforming?

Whether it is transitioning, choosing to be in an interracial relationship, a woman choosing not to have children, pursuing that profession you truly are passionate about or moving to another country, would you rather be unhappy for the rest of your life to appease others, or be happy being your authentic self? Who knows, perhaps there are others like you who want to be free and are afraid. You could be a trailblazer, as John was in 2004.

There is no time like the present to be your fearless, genuine, authentic self. There is also no time to be open to understanding others like the present. It is not enough to just be accepting; you also must stand up for and support those who are brave enough to be authentic.

Dignity is what gave that firm its reputation for excellence. Dignity is the human right to be respected. Human right is universal.

Every day while working at that firm, I was close to brilliant people, literally geniuses from all walks of life who carried themselves with dignity.

To this day, I am grateful for the experience and meeting John. He taught me an invaluable life lesson:

Be you. Be brave.

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LA Rysk

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