Olivia Hill is a trailblazer: the first openly transgender person elected to the Metro Council At-Large in Tennessee, a U.S. Navy combat veteran, public speaker, author, and staunch advocate for equality. Her passions encompass LGBTQ+ rights, women's rights, and cycling. In her own words, "I get one life. I'm going to do everything I can to live that life in a way that does not prioritize making the wealthy more wealthy while..."
Monika: As a fellow transgender woman, I'm thrilled to have this candid chat with you, Olivia. Welcome to my blog!
Olivia: Hello Monika!
Monika: Olivia, first things first - I've got to ask: what's more challenging, navigating Nashville's political landscape or surviving a family dinner with differing political views?
Olivia: Honestly, they’re equally challenging in different ways. In politics, progress often feels like trying to sprint in a three-foot-deep section of a pool—you can put in all the effort, but things will only move so fast. Family dinners with differing political views can be just as tough because, unlike in politics, where dialogue is expected, some family members can be completely closed off to discussion. That said, I’m an optimist, and I believe that, whether in politics or around the dinner table, meaningful conversations can make a difference.
Monika: From Navy blues to Nashville news, you've navigated from military service to public office. How did your time in the Navy prepare you for the political arena?
Olivia: Serving in the Navy taught me discipline, resilience, and how to operate under pressure—three skills that translate seamlessly into politics. In the military, you learn to lead, but you also learn the value of teamwork and strategic thinking. You don’t always get to choose who’s in your unit, just like you don’t get to choose who’s on the Metro Council, but you have to find a way to work together to accomplish the mission. The biggest lesson? Adapt and overcome. Whether it’s navigating a crisis at sea or navigating Nashville’s political landscape, you have to be ready for anything. And, of course, both environments come with their fair share of bureaucracy!
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| "Serving in the Navy taught me discipline, resilience, and how to operate under pressure." |
Olivia: I was at the HRC Convention in DC because I wanted to learn how to be a stronger advocate for women’s rights and the LGBTQ+ community. I wasn’t thinking about running for office—I was thinking about how I could support the fight from the outside. Then, during a Q&A session, I had the chance to speak to Danica Roem. I stood up to thank her for blazing a trail for so many of us, but before I could even finish, she stopped me, called me up on stage, and hugged me.
And then she said something that changed my life. She told me, ‘Olivia, if you want to make a difference, don’t help elected officials—become one.’ In that moment, she turned me toward the crowd and introduced me as ‘Nashville, Tennessee’s next politician.’ That was it. That was the moment I knew—if I wanted real change, I had to step up and be the one to make it happen.
Monika: We cannot avoid discussing the current U.S. political landscape, especially under the Trump administration. I won’t hide the fact that I’m a bit concerned, to put it mildly. Some may compare it to a medieval witch hunt or the hunt for communists during the McCarthy era. Is the U.S. judicial system strong enough to remain fair and impartial in these turbulent times?
Olivia: There’s no denying that these are some of the most challenging times many of us have ever lived through. It can feel overwhelming, like history is repeating itself in the worst ways. But here’s the thing—I still believe in people. I still believe in community. And I believe that real change happens when we step away from the constant doom-scrolling and start reconnecting in person. We’ve got to be more social in real life and a lot less ‘social media social.’
Politics may be a mess, but we can’t let it isolate us. The weather is about to warm up—so let’s take advantage of it. Get outside. Go for a walk. Organize a bike ride. Have a picnic in the park. Heck, even get together with some of your most trusted friends for a potluck—because real conversations happen face-to-face, not just in the comment section. As for the judicial system, I’d like to believe it’s strong enough to hold, but we can’t take that for granted. Democracy isn’t a spectator sport—it’s something we have to show up for, fight for, and protect. And that starts with us staying engaged, informed, and most importantly, connected to each other. We’re in this together.
Monika: What steps should the transgender community take to safeguard our rights? Are legal measures the only way?
Olivia: Legal measures are important—there’s no question about that. We have to fight in the courts, in legislatures, and at the ballot box. But laws alone won’t protect us. The real power comes from something much deeper—community. I believe that what we’re facing right now is going to unify the LGBTQIA+ community in a way we haven’t seen in decades. Back in the day, we were just family. It didn’t matter if you were gay, lesbian, trans, or bi—you were part of something bigger than yourself.
And honestly, I wish we had a word today that captured that same sense of belonging, one that included everyone without needing an alphabet to explain it. Some older folks don’t like the word ‘queer’ because of how it was used against us in the past, but to me, when I say I’m part of the queer community, I don’t have to explain whether I’m lesbian or trans—because that’s something I share with my intimate partner, not the world. But here’s the reality: The trans community doesn’t get to live in the shadows. We are required by law to be out—whether it’s navigating medical transitions, legal name changes, or simply existing in a world that refuses to let us blend in.
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| "We have to fight in the courts, in legislatures, and at the ballot box. But laws alone won’t protect us." |
Meanwhile, many in the gay and lesbian community still have the ability to skirt by with straight-passing privilege. They don’t have to put a picture of their spouse on their desk. They don’t have to wear anything rainbow outside of June. They can choose when and where they show up. But I’m asking—no, begging—for that to change. The world needs to see us everywhere, in every position, every location, and every situation. Because when we stay hidden, we allow the false narrative that we are some secret group lurking in the shadows. We’re not. We are teachers, doctors, business owners, parents, soldiers, public servants—we are everywhere. And it’s time for the entire community to come out, stand up, and fight alongside the trans community the way we have always fought for everyone else.
So what can we do? We stand together. We show up for each other. We build strong local communities where people know they’re not alone. We spend less time fighting trolls online and more time lifting each other up in person. We support LGBTQIA+ businesses, advocate in our schools, and make sure the next generation has role models to look up to. Yes, we fight legally. But we also fight by living boldly, loving openly, and refusing to be erased. Because when we stand together as family, we are unstoppable.
Monika: Given the recent rise in anti-trans sentiment, I’ve noticed more and more comments on social media from trans women considering fleeing the U.S. and seeking asylum in Canada. However, if an asylum claim is accepted, the individual cannot reenter the U.S. for at least five years - no exceptions. Doing so would result in losing asylum status and being barred from reentering Canada. What are your thoughts on this situation, and what advice would you give to those considering this difficult decision?
Olivia: I’m not sure I’m the right person to ask this question, because running and hiding has never been my way. I understand why some are considering leaving—I truly do. The fear is real, and the attacks on our community are relentless. But I believe the only way we’re ever going to change this is by staying, standing our ground, and fighting for the future we deserve. That’s exactly what they want. They want us to disappear. They want us to go back into the shadows, to hide, to pretend we don’t exist so they don’t have to see us. But I refuse to give them that satisfaction. The only way we change the world is by showing up—loud, proud, and unapologetically ourselves.
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| "Politics will test you." |
So if you’re struggling with this decision, I ask you to consider: What kind of world do you want to leave for the next generation? Because the fight isn’t just for us—it’s for every trans kid who deserves to grow up in a country that sees them, values them, and protects them. If we want that future, we can’t all leave. We have to stay, we have to stand together, and we have to keep pushing forward. That’s the only way we win.
Monika: For transgender individuals considering a path in public service, what advice would you offer?
Olivia: First, buckle up—because public service is not for the faint of heart! But if you’re considering this path, that means you already have the passion, resilience, and drive it takes to make a difference. My best advice? Be unapologetically you. Politics will test you. People will doubt you, underestimate you, and sometimes outright attack you. But the most powerful thing you can do is show up every day as your authentic self. You don’t have to fit into anyone else’s mold—change happens when we break the mold entirely.
Also, develop a good sense of humor. Seriously, you’re going to need it. Some people will say the wildest things with a straight face, and you’ll have to decide whether to get mad or just shake your head and laugh. I highly recommend laughing—it confuses them. Most importantly, build a strong support system. You don’t have to do this alone. Surround yourself with people who believe in you, who will remind you why you started when things get tough, and who will celebrate your wins (big and small). And finally, remember this: The fact that you’re even thinking about stepping into public service is already changing the world. So go for it. Show up. Speak up. And never forget—you belong in every room where decisions are made.
Monika: Enough politics - let’s talk about something less stressful! With such a wild mix of roles - veteran, politician, artist, advocate - how do you find balance in your life? I also heard you’re a painter… tell me more!
Olivia: Balance? Oh, I wish I had a brilliant answer for that—but honestly, I just wing it! I love what I do, and that passion keeps me going. Some people meticulously plan their schedules to find balance… I just hold on tight and enjoy the ride. The truth is, when you’re doing work that matters—whether it’s advocacy, public service, or even art—it doesn’t always feel like work. It feels like purpose. And sure, life gets chaotic, but I wouldn’t trade it for anything.
As for painting, I dabble! Art, for me, is less about technique and more about expression. It’s one of the few things in my life that doesn’t come with a deadline or a debate. It’s just me, a canvas, and whatever colors feel right in the moment. And if it turns out looking like a masterpiece? Great. If it looks like a toddler’s finger painting? Well… let’s just call it ‘abstract. At the end of the day, I think balance is less about perfectly dividing your time and more about making sure you fill your life with things that fuel your soul. And right now, mine is running on a mix of advocacy, art, music and maybe a little too much coffee!
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| "Every trans person has to find what works for them." |
Olivia: Choosing my name was one of the most meaningful decisions I’ve ever made because it wasn’t just about what sounded good—it was about who I wanted to be and the legacy I wanted to carry forward. Olivia came from Olivia Benson from Law & Order: SVU. She’s strong, she stands up for people who need someone in their corner, and she treats everyone with fairness and compassion. That’s the kind of person I strive to be every day.
Ruth is my middle name, and that comes from my grandmother—one of the strongest, most incredible women I’ve ever known. She was tough, wise, and full of love, and carrying her name is my way of honoring her strength and resilience. And Hill? That’s my mother’s maiden name. She’s my biggest cheerleader, one of the kindest souls I’ve ever met, and the person who has always believed in me no matter what. So when you put it all together, Olivia Ruth Hill isn’t just a name—it’s a reflection of strength, kindness, and the incredible women who shaped me into the person I am today.
Monika: The journey to womanhood can be challenging, but it’s also a gift that transforms our relationships - particularly with those who support us through the transition. Have you experienced this shift?
Olivia: Transition is as much about unlearning as it is about learning. As trans women, we have to learn how to walk, sit, talk, and move through the world differently. But we also have to unlearn the male privilege many of us once had—because the moment it’s gone, it’s a wake-up call. You don’t realize just how much privilege you carried until you’re suddenly treated as ‘less than.’ And that shift happens in an instant.
Each transition is unique—there’s no guidebook, no one-size-fits-all approach. Every trans person has to find what works for them. And for many of us, that journey comes with loss—friends, family, careers. That’s why it’s so important to surround yourself with steady, supportive people who lift you up rather than tear you down. One of the greatest quotes I’ve ever heard about transition is this: Your transition isn’t complete when you’re passable. It’s complete when you no longer care what other people think—when you love the way you look, the way you exist, and you live authentically. That’s the real transformation. It’s not just about physical changes—it’s about reaching a place where you fully embrace yourself. And when you do that, the relationships you build, the people who stand by you, and the life you create become even more meaningful.
END OF PART 1
All photos: courtesy of Olivia Hill.
© 2025 - Monika Kowalska
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