My name is Drew Riley, artist of the Gender Portraits series. Prudence is a self-portrait created as the third painting in a set of four self-portraits chronicling stages that I went through in transitioning.

After my stage of exploration forged a more solid understanding of identity and social confidence, I began incorporating my new selfhood into everyday life. When daily routine mixed in, a number of complications arose that made me see my gender presentations as impractical. I started taking steps to guard and relearn myself in a stage that I call prudence.

Early realizations that something was amiss came at places like the grocery store. Since my stage of exploration was primarily set in costume parties and nights on the town, my closet was largely inappropriate for daily errands. Shoes that were once comfortable in three or four hour bursts brought me blisters and blood when used as daywear. Cocktail dresses, skirts, and other loud party clothing only invited unwanted stares in the light of day and under department store fluorescents. Starting a new job, casual hangouts with friends, working out, and even changes of weather started a new round of discovering my closet’s inadequacy.

Trip after trip to thrift shops and sales racks strained my pockets despite strong efforts to stay on budget. Instead of collecting things over time, I was adding huge wardrobe sections at once, or twice, or three times because I would accidentally buy things that didn’t fit or coordinate together. In desperation, I started to lose my self-expression as I wore things that were merely close enough and wouldn’t draw attention to myself.

There’s an extra level of work that goes into expressing trans identities. Now that I was living my truth every day, being late to work resulted in deciding between presenting my gender or keeping my schedule. A cisgender woman can throw on pants and a t-shirt with no makeup and walk out the door without anyone questioning her gender. If I do the same thing, my body betrays me, and the world sees me as a man, regardless of how I feel. Sometimes I wondered if my neighbors thought that male and female twins lived in my apartment, and only the male twin was sent outside to fetch the mail and take out the trash in the early hours of the day.

Shaving, makeup and clothes started to feel like a burden, and at a certain point I decided that looking as feminine as I wanted every day wasn’t possible with my schedule. I was tired, and seeing no other solution, I comprised how I expressed my femininity to the world. After all, I can hold my internal identity as truth even if other people don't see the evidence in my external dressings.

I went on errands without makeup or a proper shave, and stopped wearing padded bras. I tried to ignore the fact that the world saw me as an effeminate or androgynous man. I brushed off the constant sirs and hims that served as a reminder of how I looked.

But this routine was not sustainable. I started getting depressed. It happened slowly, and I didn’t even notice until one day, I realized I’d been unhappy for a while. I wasn’t conditioning myself to be comfortable with extreme presentations. Instead, I was unconsciously internalizing the way the world was treating me. With my self-expression stifled, I was ignoring what I needed to feel like myself. While I had learned important lessons about living my womanhood without easy tools like clothes and makeup, I had taken things too far. At least, for me.

So, I started making a real effort to treat myself the way that I wanted. I took time to learn how to express myself while still being subtle and casual about it. I worked out a minimum makeup routine that still made me feel feminine, and to my surprise, found I now had confidence to accept my facial hair being noticeable through my speed makeup.

It is important to note that not all of this stage had to do with aesthetics. Daily dealings with people who didn’t understand or appreciate my gender and run of the mill sexism had become exhausting. It took its toll on my psyche, and after enough bad encounters, interacting with strangers started to feel daunting. I started shrugging off random people before discovering their intentions in a way I had never done before.

My safety became a new concern. One night, I went by myself to a bar to shoot photographs of a drag show, scouting for people to paint in my project. When ordering a drink at the bar, an extremely drunk man hollered that he was going to pay for the drink I ordered. I tried to protest, but he handed money to the bartender, who gave me a congratulatory smile. In that moment, in the alcohol marinated brain of the man at the bar, I was his. He would not take no for an answer, and followed me around, grabbing my arm and leaning in too close. I had come alone and really had no group to use to break away. Leaving the bar meant leaving the crowd and the safety of witnesses. I afraid of being too forceful and angering him. I couldn’t tell if he knew I was trans. He was obviously the type of person who didn’t care about consent, so was probably the type of person who would become violent if he realized my transness after yearning for me.

I got lucky, and spotted someone I had met before. I told my bar stalker that my friends had arrived and I needed to go. I briskly joined the group and after introducing myself, begged them to talk to me for a while until that man left. When leaving the bar later, an older man grabbed my hand and told me how beautiful I was, and tried to get my number. I broke free, but was suddenly aware of how far away I had parked to get free parking. It was where I had always parked, and I had always come alone. But I had always come as a man. I was simultaneously relieved and mad at myself when I reached my car. Every shadow and every stranger I passed getting there had felt like someone waiting for me.

This was not the last time the male privilege experienced in my youth left me blind to taking proper precautions. How easily I forgot I was now walking with a target on my back. I had to relearn how to think of the world, for better or for worse. On one hand, I made less mistakes when it came to my safety; on the other hand, I now lived with a certain level of paranoia hovering over me. To this day, I miss not being coveted by creeps.

There was also a social and intellectual transition happening where I was learning what type of woman I was in new situations that I hadn’t visualized myself in. The most notable of which was learning how to be professional as a woman.

I entered the workforce very early in life. For a long time, people were quick to dismiss me due to my age. Being a leader who knew how to marry assertiveness and diplomacy became my some of my most cherished and invaluable traits. So when I started being self-conscious about being too masculine when exercising authority, the internal crisis that resulted was powerful.

It wasn’t that I didn’t think I could be a powerful, professional woman. I just hadn’t given enough thought to what that looked like for me. When you fantasize about your life in a new role, you focus on the glamorous and fail to ponder the mundane. I found myself in situations that I hadn’t mentally prepared for, and would be torn about what to do. Without thinking, I lower my voice when getting a group's attention, so that I project from a bass that I don’t normally talk in. My stance changes to become wider and taller with my energy forward. A lot of these traits are typically considered alpha male, and I was scared of losing my femininity the moment I took charge.

Of course, this problem is compounded by society’s view of women in commanding positions. A lot of women struggle with how to be authoritative in a world that gives them few examples of powerful women. Again, I was struggling with a loss of privilege at the same time as getting to know myself. People treated me differently as a woman, and a lot of the similar frustrations experienced as a young professional were resurfacing.

The solution to this problem was the same as it was in my youth. Changing nothing, I needed to be the best professional I could be, politely, without apology or excuses. When people couldn’t see past their preconceived notions, I had to continue forward without their approval. It took me a little time to shake my insecurities, and shift my perspective, but I got there. To this day I don’t know how femininely people perceive me when I’m visibly in charge, but I know that inside I feel like an Amazonian warrior, and that’s all that matters.

Ultimately, even though my stage of prudence pushed me to be so cautious about my presentation that I often lost myself, I learned a lot as a result. I learned how to command my gender without my appearance doing all the work, while staying true to my selfhood and personality. I also learned how to balance being more cautious with strangers and my safety with my naturally trusting, optimistic nature. Mostly, as in my previous stages, I needed practice.

By the end of this phase, my old party clothes felt more like costumes than true representations of me. I was finally able to hold my identity in my head in a large variety of contexts and see myself as a more whole person, allowing me to enter into my final stage of transition.

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