Monika: We all know the journey to being our true selves comes with a heavy price, like losing friends, family, jobs, and all that. I must say I am one of them. Did you have to pay a heavy price for being you? What was the toughest part of your coming out?
Olivia: Here’s a response that keeps it uplifting, positive, and deeply personal: I lost everything—friends, family, my career—every piece of the life I once had is now gone . But here’s what I tell people every time I step on stage as a public speaker: I want you to stop for a moment and think about your greatest wish in the whole wide world. Maybe it’s becoming Miss America. Maybe it’s being a billionaire with your own island. Maybe it’s being the CEO of a major corporation, being 20 years old again, or having perfect health.
Whatever that wish is, imagine waking up tomorrow morning and realizing that it just came true!! That’s what every single day feels like for me. Because after almost 50 years of wishing, hoping, and dreaming—I finally get to wake up as my true, authentic self. Yes, it was hard. Yes, it was painful. And yes, I had to pay a heavy price. But was it worth it? Absolutely. Because no amount of loss can compare to the freedom of finally living as the person I was always meant to be. So to anyone out there who is struggling, afraid of what they might lose, I can tell you this: The road isn’t easy, but the view from the other side? It’s beautiful. And you are worth the journey.
Monika: Many of us have concerns about “passing” and how society perceives us. Did you face similar worries during your transition, and how did you address them? I know for me, there were moments when I felt like I was in a never-ending game of "Is she or isn’t she?" played by strangers in grocery stores.
Olivia: Here’s a thoughtful, uplifting, and slightly lighthearted response: Oh, I’ve been there! That never-ending game of ‘Is she or isn’t she?’—played by total strangers at the grocery store, the gas station, or just walking down the street. And let me tell you, it can be exhausting. Like many trans people, I did worry about passing in the beginning. I think we all do at some point because society puts so much pressure on appearance. But the truth is, ‘passing’ is a moving target. No matter how you look, there will always be someone who thinks they have the right to judge. And one day, I realized—I don’t owe anyone an explanation or an approval rating.
Like I said earlier in a previous question you asked... ”Your transition isn’t complete when you’re passable. It’s complete when you no longer care what other people think—when you love who you are and live authentically”. That’s the moment I let go of the pressure to ‘pass’ and started focusing on just being me. And you know what? When I walk through that grocery store now, I walk with confidence. Because I’m not playing their game anymore—I’m living my life. And that’s the best feeling in the world.
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| "I think that the path that I have lived has made me who I am. It made me resilient. It made me stronger." |
Monika: If you could tell your younger self one thing about being a transgender woman, what would it be?
Olivia: i’m not sure that I would want to talk to my younger self. I think that the path that I have lived has made me who I am. It made me resilient. It made me stronger. It is built me into the woman that I am today with my life experiences that I have but if some miraculous thing happened and I could travel back in time, I would keep it simple and just say this... I would take her hands, look her in the eyes, and tell her this: You are not broken. You are not wrong. And you are not alone.
Monika: Finally, what’s next for Olivia? What dreams and goals are you working toward now?
Olivia: As long as the public keeps voting for me, I’m going to keep climbing. I’ll continue to serve, advocate, and push for change until I run out of space to climb—because there’s still so much work to be done. But politics isn’t my only path forward. I just finished my book last week, and I’m incredibly excited to find the right publisher to help share my story with the world. I want it to reach people who need to hear it—people searching for hope, understanding, and maybe even a little courage to step into their own truth.
I’m also growing my public speaking business, Olivia Speaks, so I can travel the country, stand up for women’s rights, LGBTQ+ rights, and inspire others to step into their power. Advocacy doesn’t stop at the city council chambers, I want to be in rooms where conversations can lead to real, meaningful change. And once that book is out? I’m sitting down to write another. One that dives into what it really means to transition—not just the medical steps, but the emotional journey. So many of us enter transition trying to fit into the image we think we’re supposed to be—ultra-feminine, ultra-masculine—because that’s the framework we’ve had our whole lives. But around the five-year mark, something shifts. You stop seeing gender through the lens of the past, and you start seeing yourself, your true self, beyond expectations or stereotypes. That’s a journey worth writing about. So what’s next? More books, more speaking, more fighting for the things that matter. I’m just getting started.
Monika: Olivia, you've done so much - politics, military service, art, advocacy, and so much more. But here’s the real question: What’s next? A reality TV show? Maybe a superhero role? Or are you planning to launch your own line of cycling apparel? Whatever it is, I’m sure it will be nothing short of legendary! Thank you so much!
END OF PART 2
All photos: courtesy of Olivia Hill.
© 2025 - Monika Kowalska
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