Penny is a woman whose story unfolds with quiet strength, deep honesty, and an extraordinary sense of grace. Penny is a landscape architect based in San Francisco, a partner at her firm, an artist at heart, and someone who has learned how to build not only physical spaces but also emotional ones where authenticity can finally breathe. Raised on the isolated beauty of Catalina Island and shaped by years of personal reflection, creative work, and love, her journey is one of patience, resilience, and profound self-discovery. Penny’s words carry the calm confidence of someone who has spent a lifetime listening closely to herself, even before she fully understood what she was hearing. In this interview, Penny speaks openly about transition, love, identity, and the subtle ways becoming oneself can transform every corner of life.
From her deeply grounding relationship with her wife and family, to the emotional clarity she found through journaling and hormone therapy, to her thoughtful reflections on womanhood, visibility, and community, Penny offers more than a personal story. She offers reassurance, light, and connection. Her voice is gentle yet powerful, reminding us that authenticity does not arrive all at once, but grows steadily when met with courage, compassion, and love. What makes Penny’s story especially moving is the way she approaches visibility, not as performance, but as an act of quiet generosity. By sharing her experiences publicly, she has created a point of recognition for others who are still searching for language, courage, or simply the reassurance that they are not alone. Penny does not present herself as a symbol or an answer, but as a real woman living an honest life, navigating fear, joy, doubt, and freedom with remarkable clarity. In doing so, she reminds us that transition is not only about becoming, but about learning how to live fully inside that becoming, and how sharing our light can help others find their way too.
Monika: For those who may not know you yet, could you share a little about yourself and your background?
Penny: Oh definitely. I’m a 39-year-old trans woman living in San Francisco with my wife and our dog. I’m a landscape architect and a partner at my firm, which still feels a little surreal in the best way. I love the outdoors, and I’ve somehow managed to turn that into a career designing spaces that invite others to share what I love. Outside of work, I’m an amateur artist, a clumsy musician, and a pretty good baker.
Monika: What was it like growing up where you did?
Penny: I grew up on Catalina Island, about 26 miles off the coast of Southern California. It has one small, isolated town, and growing up there in the nineties was idyllic in a way that’s hard to replicate, with one small school where I formed some of my deepest friendships that continue to grow with time. After graduating, I moved to Arizona to study landscape architecture at Arizona State. I earned my bachelor’s degree, graduated with honors, and won two national design competitions. I still have an affinity for the Sonoran Desert, the plants, the light, the summer storms. When I graduated in 2008, right at the beginning of the recession, I managed to land a job and just kept building from there. That journey culminated in becoming a partner at my firm in 2023, which also happened to be the year I came out publicly as a trans woman.
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| "I’m not someone who instinctively knows what I’m feeling in real time." |
Monika: How did you meet your wife, and what role has she played in your life?
Penny: I met my wife while in Arizona, when my personal life felt pretty unstable. Before her, I didn’t have much balance, I didn’t know how to hold myself together for very long. I had a talent for going full throttle and then crashing. But she loves me with a kind of patience and fierceness that makes me feel safe. Because of her, I learned that I could show someone my deepest fears, and still be met with understanding and love. Ultimately, she gave me a center of gravity, grounding me in a space where I could take the time to understand myself.
Monika: You mentioned journaling, how did that shape your understanding of yourself?
Penny: I’m not someone who instinctively knows what I’m feeling in real time, so I’ve kept a journal since I was a teenager. It started as a way to clear the existential clutter, but over time it became a record of who I was becoming, even when I didn’t have the words for it yet. I never really went back and read it until I started questioning my gender. I remember thinking, surely I would have figured this out already if I’d been carrying decades of dysphoria, depression, and poor coping mechanisms. And sure enough, there was this throughline that didn’t outright scream I’m trans at the time, but reading it all through at once, I was able to piece together what all those past versions of myself were trying to say.
Monika: Sharing personal moments, especially those that touch on identity, love, and self-discovery, can be both empowering and vulnerable. What inspired you to open up and share your intimate life experiences on social media?
Penny: I shared for a few reasons: I wanted to be understood, I wanted to reach others like me, I wanted to offer firsthand knowledge in a time when misinformation can do real harm, and also because it was convenient. I had told my closest friends and family one by one, in person or over the phone, and eventually I reached a point where I was ready to tell everyone. Posting felt imperfect, but it let me speak once instead of repeating myself. I intentionally made my profiles public too because I wanted to normalize and humanize being trans. My profiles are boring af, I’m not trying to hurt anyone, I’m just trying to get by.
Monika: Engaging with followers on social media often leads to a flood of curiosity and heartfelt messages. Do you receive a lot of questions from your audience? What are the most common things they ask about, whether it’s advice, personal experiences, or words of encouragement?
Penny: I received an overwhelming amount of heartfelt messages and encouragement, and I still do. I genuinely thought my world would get smaller, that people would drift away or stay quiet. Instead, it grew. People reach out with questions about transition and self-acceptance, but mostly they’re just looking for connection. I’ve learned that people want more light in their lives, and these days I feel like I’m shining pretty brightly.
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| "I chose Penny partly because of my copper hair." |
Penny: It took me a while to find a name that felt natural. At first, I wasn’t even sure I wanted to change my name, but eventually I realized I couldn’t keep moving forward in the ways I needed to without it. I chose Penny partly because of my copper hair (which has always been my favorite physical trait), but also because it echoes my mom’s name. It felt like something my parents might have chosen if I’d been born a girl. The first time I said it out loud, there was no question anymore. It didn’t feel new or performative, it felt like me.
Monika: When you came out, did your mother embrace you as her daughter? And do you feel any connection to her in the way you look, carry yourself, or even in your style and mannerisms?
Penny: My mom has been very supportive and embraced me as her daughter right away. We definitely look alike, and she has the most beautiful hair. It's been strange and wonderful watching that resemblance become more visible over time. I catch glimpses of her when I look in the mirror, in certain expressions, even in small mannerisms I never noticed before. As I’ve become more myself, we’ve grown closer than ever, like we’re our own little team. Our relationship feels more open now, more layered, and richer. There’s something deeply grounding about that connection, like a reassurance that this isn’t a departure from my family, but a natural continuation of it.
Monika: I finally felt free after my transition. How about you? Was there a single moment, or maybe a series of moments, where you truly felt like you had stepped into your most authentic self?
Penny: Yes, freedom in a way I didn’t know was possible. It wasn’t a single moment so much as a series of them. As I told more and more people, I felt lighter and lighter, and I could stand taller and taller. I had been growing so small in the years leading up to it, feeling trapped, like I’d crawled to the end of a cave with nowhere left to turn.
As I came out, a lifetime of pent-up fear began to loosen its grip, the constant vigilance, the belief that if anyone truly saw me I’d be punished, humiliated, or abandoned. I had spent so long bracing for consequences that I never realized how much energy it took just to exist. Transition didn’t make life easy, but it made it honest, and in that honesty I felt something I’d never felt before….space! Space to breathe, to feel, to move through the world without hiding. When I was no longer afraid of being my authentic self is when I finally felt free.
Monika: Many transgender women have a variety of experiences with hormone therapy. Looking back, how do you feel about the physical and emotional effects it’s had on you?
Penny: Estrogen didn’t change who I was so much as it changed how I experienced the world. Starting hormones felt like stepping out of black and white and into color. Emotionally, things softened and deepened at the same time, feelings gained texture, nuance, warmth. Joy became fuller, sadness became clearer, and the constant background noise I’d lived with for decades finally quieted. Physically, my body began to feel like a place I could inhabit instead of manage. It doesn’t fix everything, but for anyone living with dysphoria, it can be essential in gaining a clearer understanding of themselves.
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| "The hardest part of coming out wasn’t the act itself, but finding the right words for the people in my life." |
Monika: The journey to being our true selves often comes with a heavy price, losing friends, family, and sometimes even our jobs. What was the hardest part of coming out for you, and how did you navigate it?
Penny: The hardest part of coming out wasn’t the act itself, but finding the right words for the people in my life. I knew everyone held a different version of me, so I found myself rehearsing a different conversation for each person, trying to meet them where they were. It mattered deeply to me that they understood the WHY. I was afraid that if I couldn’t explain it clearly enough, they wouldn’t believe me, or they’d think I was delusional. I carried a lot of imposter syndrome, especially because I didn’t fit the narrow story many cis people expect from trans women. I didn’t grow up in dresses or playing with Barbies, and for a long time I worried that would make my truth harder to accept. What I had to learn, and then explain, was that there are many ways to hide who you are, and many ways to survive without being seen. Coming out meant translating that survival into language others could understand, even when I was still learning it myself.
Monika: Do you remember the first time you saw a trans woman on TV or met one in real life that helped you realize, “That’s me!”?
Penny: I think the first time a trans woman really crossed my radar was when Laura Jane Grace came out in a Rolling Stone article in 2012. I remember reading it over and over, not because I immediately thought “That’s me!”, but because something in me quietly locked onto the possibility. It felt radical in the simplest way, like realizing a door existed that I’d never been allowed to look for. At the time, I framed it as admiration, thinking how cool it was that someone could actually do that, live that openly. I didn’t have the language or courage to follow that thread yet, but it planted something important. It showed me that this wasn’t just an abstract idea or a private fantasy, it was a real life someone could step into.
Monika: Many of us feel the pressure to “pass” as women, and even after surgeries, society keeps judging us. How do you personally deal with the outside world’s expectations?
Penny: I struggle with this every day. There’s a constant, low-level awareness of how I’m being read (my voice, my face, my body, my mannerisms), and it can be exhausting. Some days I catch myself shrinking, trying to smooth off anything that might invite scrutiny. Other days I remind myself that passing isn’t the same as peace, and no amount of perfection will ever fully satisfy a world that’s invested in policing womanhood. What helps is slowly shifting my focus away from being legible to others and back toward being honest with myself. I’m learning that my womanhood doesn’t need to be earned through approval. It’s already mine, even on the days it feels fragile.
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| "I’m learning that my womanhood doesn’t need to be earned through approval." |
Penny: The U.S. varies wildly for trans people in how we’re treated, accepted, or even recognized at all. I’m incredibly lucky to be in San Francisco, which is one of the safest places in the world for trans people. There’s even a designated Transgender District that the city formally recognizes, and that kind of visibility and community matters more than people realize.
That said, it’s hard to feel optimistic right now. The broader direction of our government doesn’t offer much reassurance, and the road ahead feels heavy, especially for trans people who don’t have access to supportive communities. I worry most about those who are isolated, no one should have to navigate this alone. I try to support local trans organizations when I can and stay engaged in the queer community, because right now that feels like the most meaningful way I can show up, by staying connected, visible, and supportive of one another.
Monika: I remember the time right after my transition, it was pure euphoria. My closet is still full of dresses and shoes that I literally bought by the dozens back then, and I must have tried on hundreds. I felt like I had to make up for all those years that were taken from me. Did you feel the same way?
Penny: Absolutely, my bank account will never fully recover! That early euphoria came with a lot of catching up. I suddenly had to build a sense of style from scratch, not just clothes but preferences, instincts, and confidence. Learning how to dress for my coloring and body type, figuring out what makeup goes where and why, which brands actually work for my skin, and realizing that an outfit is no longer just pants and a shirt but a whole composition. It was a lot.
There were moments where it was genuinely overwhelming, especially layered on top of the emotional intensity of those early days of transition. I was trying everything at once, not to perform femininity, but to find myself inside it. I was learning how to inhabit a body and identity I’d waited a long time to meet.
END OF PART 1
All photos: courtesy of Penny.
© 2025 - Monika Kowalska
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