There are journeys that unfold quietly in the margins, and then there are those that radiate courage in every step, Jessika’s story is the latter. At 41, Jessika Scherff is a woman who has walked through decades of silence and self-erasure, only to rise, finally, into the fullness of her truth. She began her medical transition in August 2023, but her inner knowing stretches back to the tender age of eight, when nightly prayers carried a wish to wake up in a body that felt like home. For years, Jessika wore a mask, hiding her femininity beneath layers of expectation, survival, and socially sanctioned masculinity. She worked in construction and auto mechanics, raising two sons, building a life that looked solid on the outside, even as it splintered within. Her path hasn’t been easy. It’s been marked by heartbreak, resilience, and the aching absence of her children, particularly the soft silence left by her youngest son. And yet, amid these losses, Jessika has chosen visibility.
With vulnerability and grace, she has opened her life on social media, not to seek attention, but to claim authenticity, and in doing so, to offer hope. Her journey through vaginoplasty and breast augmentation, her reflections on motherhood, mental health, and the challenges of transitioning in a red state, all speak to the depth of a woman who has known what it means to fight for her reflection and finally see someone beautiful staring back. A proud Wiccan with a flair for witchy, bohemian fashion, Jessika embraces dark eyeliner, flowing skirts, and a mystical spirit that matches the strength in her voice. Whether sharing makeup tips, personal struggles, or fierce thoughts on trans rights, she remains unapologetically herself. Jessika’s life reminds us that becoming isn’t always about discovery, it’s about remembering, returning, and reclaiming the person you were always meant to be.
Monika: Hello Jessika! Thank you for accepting my invitation.
Jessika: I thank you very much for reaching out and giving me this opportunity.
Monika: For readers meeting you for the first time, could you share a bit about who you are and the journey that brought you here?
Jessika: Well, my name is Jessika. I’m 41 years old. I started medically transitioning in August of 2023. Around that time, I came out to my siblings, then to my two boys, my ex-wife, and eventually, in August of 2024, I legally changed my name and came out socially at work. As of March 25, 2025, I’ve undergone both vaginoplasty and breast augmentation.
I’ve known I was transgender since I was 8 years old. Over the years, I would crossdress in secret and pray every day to wake up as the opposite gender. I can’t even tell you how many times a day I sat there wondering what life would be like. How many nights I’d go to bed hoping, praying, that something would change.
When we moved to a small country town, I was bullied a lot in middle school for being feminine in my gestures. To survive, I created a masculine persona, trying to become what I thought everyone wanted to see. That’s when depression started to sink in, little by little. I developed social anxiety. I hated my image in photos, hated looking in mirrors, hated being naked. I wouldn’t swim because I didn’t want to expose my body.
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| "I held onto that masculine identity for years." |
That’s when I finally decided to go for it. I found a therapist, and we talked everything through. She identified that my depression was rooted in gender dysphoria. After going through the usual questions and scenarios, I was diagnosed. At first, it started as crossdressing and exploring. But once that door was opened, it felt like an explosion, of exploration, of validation, of finally being seen. And that’s what brought me here.
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?
Jessika: I think what really helped me open up and share my journey was pushing myself. Putting it out there kind of made it real, it cemented it. I had postponed coming out for so long, so when I started posting my story on Instagram, it was a huge step. In fact, Facebook played a big role in my social transition. I posted about the legal name change and told people I would let everyone know more when the time felt right. I promised myself I’d come out officially once everything was finalized. Then I got the letter in the mail confirming the change. I thought I had 60 days, but it showed up within a week, and that’s when I came out socially at work.
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?
Jessika: I think a lot of the comments I get in my DMs are words of encouragement, validation and praise. I also get questions from people asking for advice or wanting me to share my experience with certain things. Lately, it’s mostly been about my surgery, and I’ve been doing my best to educate people about the process of bottom surgery. Not a lot of people talk about the pain and the challenges you face for three months or even longer.
Monika: So many of us navigate the roles of wives, mothers, and daughters, often carrying the weight of our pasts and sometimes longing to leave it all behind. Yet, you’ve chosen to embrace your identity with such strength, becoming an advocate for transgender rights and vocal about presenting a positive image of our community in society. In the face of all this, have you ever felt the pull of staying in the shadows, of simply being seen as a woman, without the added layers of being a transgender woman?
Jessika: I think there was a moment when I considered just staying in the shadows and letting people believe whatever they wanted. But most of the time, I embrace who I am. I’m transgender. I’ve been through a lot to get to this point, and I can’t deny that I lived 40 years of my life as a male. I have children, and I have a past. Even though it’s been a struggle and I’ve lost a lot of dear things along the way, I’m not ashamed of who I am. I spent too many years feeling shame, I don’t have room for that anymore.
Monika: Choosing a name is such a deeply personal decision, one that can hold layers of significance and meaning. How did you come to choose the name Jessika? Does it carry a special resonance for you, perhaps representing a part of your journey or embodying a particular feeling or aspiration?
Jessika: It’s kind of silly, but I actually picked this name back in 2009. One of the ways I allowed myself to feel feminine was by playing a female avatar on PlayStation Home. It was a virtual world where you could take on a persona, chat, either by text or voice, and just be who you wanted to be. I remember talking to someone at an internet café, and they asked me for my name. I said, “It’s Jessica.” Over the years, that evolved into Jessika. As for my middle name, Katherine, it came from a rogue character I created for Dungeons & Dragons. I loved the name so much that it stuck, and now it’s part of me.
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| "I’m not ashamed of who I am." |
Jessika: This is a very rough subject. When I came out, my ex-wife was the only person who reacted horribly, and to this day, she’s still the one person who’s been the absolute worst about it. She has since accepted that I am who I am, and she’s not as bigoted in her views now, but the damage was done. My oldest son, who was 11 at the time, didn’t seem to mind at first, but he eventually stopped coming around. My youngest, who was six at the time, now seven, responded with curiosity and became one of my biggest allies. He would speak up if his grandmother or mom said anything bad about me. He loved coming over.
That lasted until February of this year. Once he learned about the surgery, I think he realized that the physical representation of his father, the person he remembered, wasn't coming back. He’s been processing it almost like a loss, like a death. Since then, he hasn’t returned. He doesn’t want to talk to me on the phone. He doesn’t want to meet up for a quick dinner or even a hug. That’s been the hardest sacrifice I’ve ever had to make. I wish I didn’t have to make it, because I really miss his hugs. I miss having them on the weekends, laughing with him, and watching TV together.
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?
Jessika: I didn’t feel free at first. I remember being so scared in the beginning that I actually stopped taking my pills two months in. But that made it really hard to get through the day. The depression came back, the anxiety came back, and the dysphoria came back. So I grabbed my journal and started writing down all the feelings that were hitting me every single day. I needed something to remind myself, if I ever had doubts again, what I had been through, and why I started.
Once I moved into my apartment and away from my parents’ house, where I had been staying briefly, I started taking my pills again. And I felt it. I still couldn’t look in the mirror because I saw the guy, but I started to feel a connection. I think it was the day after my surgery. I took a couple selfies for Instagram, makeup-free, oxygen hose, monitors all over me, and I remember looking at those pictures and saying, “Wow. She is beautiful.” And even now, when I look in the mirror, I smile. Because I finally see her.
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?
Jessika: The hardest part has got to be not seeing my children. Not necessarily because of my ex-wife, or at least I don’t think so, but because they haven’t been able to accept the reality. I don’t think a day goes by that I don’t miss them. The day my youngest wouldn’t come over to give me a hug, that’s the day my heart really broke. I’m still trying to figure out how to navigate it. Most days, I just try to ignore it. But you can imagine, it’s caused more than a little bit of depression.
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!”?
Jessika: No, I don’t remember seeing anyone on TV who was transgender. I mean, I remember Mrs. Doubtfire and MASH*, but those were just cross-dressing roles played for laughs. I do remember looking at Nicole Kidman in Practical Magic and thinking, “I wish that was me.” It wasn’t just her looks, it was her whole style and demeanor. I don’t think I ever had a trans influence in TV or movies growing up that made me want to be a woman, I just felt it. But over the years, there were definitely movies where I looked at a character and thought, “I wish that’s what I looked like.”
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| "I’m very afraid for the transgender community in our country." |
Jessika: I’ve gotten a lot of hateful comments on threads, Instagram, and Facebook. At first, they really hurt and got to me. But then I reminded myself that these people are ignorant, they don’t sit at my table. If someone makes a comment about me but doesn’t sit at my table, why should I let it bother me? It’s kind of like, if you don’t pay my bills, you don’t have a say in how I live my life. I adopted this saying: “You don’t even matter. If you died tomorrow, I wouldn’t blink, I wouldn’t even know. So why am I letting you ruin my day?” It might seem a little dark, but it’s a way for me not to give them any mind.
Monika: What are your thoughts on the current situation for transgender women in your country? Do you think we are progressing, or does it feel like we’re moving backward?
Jessika: I’m very afraid for the transgender community in our country. The blatant attacks by the Republican party to try and erase us are awful. It feels like we’ve stepped further away from scientific fact and truth, and instead embraced religious doctrine. You can’t replace science, biology, and psychology with religious sayings, science is proven. I think transgender women are targeted more specifically because of this harmful stigma that we’re somehow predators, and I don’t think people even care that trans men exist. But the attacks on transgender women affect all of us. I truly believe it’s going to get worse, and living in a red state scares me every day.
Monika: How would you describe your personal style? Do you follow any specific fashion trends, or do you have go-to outfits that make you feel confident?
Jessika: I’ve tried a lot of different styles, but I’ve landed on a very witchy, bohemian, goth look. I like low-cut tops, fun skirts, and dangly jewelry. Being a Wicca, my style reflects that. My makeup is usually darker, very smoky or cat-eye.
Monika: Do you love playing around with makeup, or is it more of a “throw on the basics and go” kind of vibe for you?
Jessika: Oh, I enjoy playing with different colors. Most of mine are very dark, but I also use a lot of neutral tones. I don’t really play much with bright colors , I think the only bright color I use is a pink lipstick that goes well with almost everything.
Monika: By the way, do you like being complimented on your looks? Do you find it easy to accept compliments, or do you struggle with believing them?
Jessika: I love being complimented on my looks, but I also have a hard time believing it. It feels like a dream to have people find me gorgeous or beautiful, so I guess it’s still hard for me to fully accept that this is my reality now.
Monika: Did you ever feel pressure to meet a certain ideal of femininity, like I did by trying to look like the women around me?
Jessika: There’s definitely pressure to look feminine. I worry about my jawline, my chin, and my nose. I wear wigs because I don’t have a lot of hair. Then I found out that Halsey wears wigs, and I thought, “If she can, then I can.” After that, I started noticing jawlines on people like Julia Roberts and Sandra Bullock, who also have a cleft chin. I realized these traits I have are shared by different women in the spotlight. I also noticed that women come in all shapes, sizes, and facial and body structures, and look how gorgeous they are. So, I started loving my face more, loving my wigs more, and gaining the confidence to just say, “This is who I am.”
Monika: Do you remember your first job interview as a woman? Did you feel nervous, or did you approach it with confidence?
Jessika: Luckily, I haven’t had a job interview presenting as a woman. I’ve worked at the same place for over 15 years, and they’ve accepted my gender, respected my name, and made it really easy to transition while staying in my existing position. I really love my job.
Monika: When I came out at work, my male co-workers suddenly started treating me as if my transition had lowered my IQ. Did you experience a similar shift in how people perceived your intelligence or competence?
Jessika: No, not at all. I remember when I came out at work, telling them my new name and opening up about everything, how I’d been dealing with depression for a very long time, that I was suicidal, and that I was diagnosed with gender dysphoria. I had been hiding it for a year, and it was really hard. I was worried about what people in the shop would say. But I remember the overwhelming support I got from the five people in the office. One of them said something amazing to me: “Don’t worry about those guys out there. We’re your family here. We got you.”
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| "The most surprising part of my transition was the emotional avalanche." |
Jessika: I think the most surprising part of my transition was the emotional avalanche. I call it that because it felt like I went from not crying at all one day, to now crying at the drop of a hat. I’ll watch a movie I’ve seen a hundred times and suddenly start crying at parts that never affected me before. I cry from happiness, sadness, laughter, what used to be seen as weakness, I now love it. Another surprise has been the internal orgasms. I’ve never experienced such intense pleasure that hits me two, three, or even four times in a row. That was completely unexpected.
Monika: Many trans women are writing their memoirs these days. Have you ever thought about writing your own book, and if so, what would its central message be?
Jessika: No, I haven’t thought about writing a book about myself. I have started writing a fiction book based on a character of mine from Dungeons & Dragons. It’s a fantasy novel , what began as just a backstory became a short story, which is now turning into a chaptered story that might eventually become two or three novels.
Monika: Finally, what’s next for Jessika? What dreams and goals are you working toward now?
Jessika: That has been a difficult thing. I felt like I was at a crossroads for so long and didn’t have a clear plan. I decided that I’m going to look for a piece of property, put a little house on it, and love my life. Finding someone to love would be nice, but I’m not going to wait for that to plan my future. As you know, it’s hard to find someone who wants to date a transgender woman, so I’ll admit I kind of gave up on that aspect.
Monika: Jessika, thank you so much for sharing your journey and insights.
Jessika: Thank you for allowing me to share some of my life.
All the photos: courtesy of Jessika Scherff.
© 2025 - Monika Kowalska
I hope her boys come around and she gets that very important hug.
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