Some stories remind us that no matter how far we fall, we can rise again, stronger, wiser, and more radiant than before. Today, I have the true privilege of sharing one of those stories with you. My guest is Kendra Brill, the remarkable woman whose life journey is captured in The Kendra Brill Story (2017). Kendra’s life has not been an easy road. She has walked through struggles that many of us can hardly imagine, addiction, incarceration, rejection, loneliness. She has known what it means to stand at rock bottom. But she has also discovered something even greater: the courage to climb, the strength to transform, and the grace to embrace her authentic self as the woman she was always meant to be. Her story is not just about survival, it is about triumph. It is about finding family in unexpected places, and about being lifted up by love when the world seemed determined to pull her down. It is about believing that faith can heal, that wounds can become wisdom, and that no person is ever too broken to be made whole again. What makes Kendra so inspiring is not simply that she overcame hardships, it is the way she turned those hardships into hope for others. She shares her truth openly, without shame, because she knows that visibility saves lives.
She wants every person in the LGBT community who feels lost to know they are not alone, that change is possible, and that love, both divine and human, can reach even the darkest corners. Kendra’s courage shines especially bright when we think of the challenges she faced as a transgender woman. She fought for her name, her dignity, and her right to live authentically. She began her transition under the most terrifying circumstances imaginable, in a men’s prison, and yet she found a way to hold onto her truth. That kind of bravery is not just remarkable; it is transformational. Today, Kendra stands as living proof that redemption is real. Her life is a testimony that no past mistake can define us, and no obstacle can stop us if we believe in ourselves and keep moving forward. She reminds us that scars do not make us weaker, they make us luminous, because they tell the world that we survived. It is with admiration, respect, and joy that I welcome you into this conversation with Kendra Brill. May her words uplift you, remind you of the power of resilience, and inspire you to believe, no matter what your path looks like, that transformation and love are always within reach.
Monika: Today, I have the great pleasure of speaking with Kendra Brill, the inspiring woman at the heart of the biographical book The Kendra Brill Story (2017). Welcome, Kendra!
Kendra: Hello, Monika! I love your blog!
Monika: For readers who may be discovering your story for the first time, how would you describe the woman you are today?
Kendra: I'm truly blessed to be the authentic woman that I am! I went from being that sad and lonely William, that everyone knew and loved, to being Kendra, a strong and dependable woman.
Monika: What brings you joy in your everyday life?
Kendra: I have a loving family that I’ve always wanted and a house that I was blessed with. I have people from all walks of life surrounding me, filling me with love and encouragement that I truly value. It might not be the family that I was born into, but it is my family through Jesus Christ.
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| With "The Kendra Brill Story." |
Monika: After everything you’ve experienced, how important has that love and support been in shaping the woman you are today?
Kendra: After the hell that I’ve been through, it really feels wonderful to be in a loving and caring community. Without their support, I’m not sure if I would have made it as far as I have. They accept the addict, the prostitute, and the ex-incarcerated parts of me. They truly love me for every part of me. I never thought that I would write a book, go to prison, be addicted to drugs, or learn what God’s love is, but everything leading up to this point has made me into the woman that I am today, with a book, a loving family, and God’s love. It’s truly amazing! Sometimes it’s hard for me to wrap my head around it all.
Monika: What inspired you to share your life story through a book, and what message did you hope it would carry for the LGBT community?
Kendra: I wanted to help the LGBT community. I wanted to show them that they aren’t alone, that others have been through the same things they’ve been through. That it’s never too late to change your life and walk a different path than I did. I wanted to let the LGBT community know that if you keep fighting and working towards your goal, one day you will have what you need. Nobody is too broken to be fixed!
Monika: Your life has included some extremely difficult experiences. How do you hope your story of overcoming challenges can inspire others?
Kendra: I had been incarcerated for long portions of my life, I’ll never get that time back. I was an addict to alcohol and a prostitute to feed my addiction. If I can change after all of that, so can you, so can anyone. It might be hard, I’m not going to lie and say it won’t be, but it’s worth it. It will heal those wounds, your scars, and your heart.
Monika: Faith plays a strong role in your journey. How has it shaped your transformation and your message to others?
Kendra: I wanted to let the LGBT community know that God does love you and that there are people out there who truly love you for who you are. No matter what walk of life you chose in the past, God still loves you, and there are people out there who still love you! I asked God to remove the addiction from me, and He did. He does care, He does hear your cries, and He is listening! All you have to do is want to change and ask God to change your life for the better. Put your life into His hands and let Him guide your path, you’ll change for the better, and you’ll finally be able to say, with truth, that you love yourself, like I did!
Monika: How did you come to collaborate with Tess de Carlo on your book? Was it something you planned, or did it feel more like fate?
Kendra: Actually, it was more or less fate. I was downtown watching the ball drop when I made a New Year’s resolution to write a book, then Tess messaged me only minutes into the New Year and asked if she could write my book. It was like fate brought us together so we could bring people back to God. Seven is a lucky number of mine because I was born on the seventeenth day of September. One is a new lucky number because of the first of the year. I'm really big on numerology, and whenever I see my lucky numbers, it’s like a sign from above that I need to take action or that I’m exactly where I’m supposed to be in life. It was a sign from God that I needed to write my story and get it out there for the world to hear.
Monika: Your book is very candid about your life, including difficult experiences such as addiction, incarceration, and prostitution. What made you decide to be so open about these parts of your story?
Kendra: I’m an open book. I have no secrets. We all fall short of the Glory of God. I would hate for any girl to do these things. The addiction turned me to prostitution and incarceration. I asked God to remove the addiction from me so that I wouldn’t bear any more chains that held me in captivity. And God blessed me with His grace and removed the addiction from me! I no longer need the drug to live because I am living my truth through God!
Monika: How have your personal experiences shaped the way you support and inspire other trans women?
Kendra: I took my experiences and my pain and did something to help other people. But not only am I helping others with my life story, it’s also helping me to stay clean and on the right track. I’m living proof that it’s never too late to turn back and change your ways for Christ.
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| With her transgender daughter Mya, playing on snap chat. Kendra made a snap, that said this is a dog eat dog world, you better get in where you fit in. |
Monika: Were there specific challenges you faced that you hope other trans women can learn from?
Kendra: Another useful aspect of my life that can help women is my fight for my legal name. I was denied my name change by Judge Dennis Lee Hupp and told I had to undergo Gender Reassignment Surgery in order to get my legal name, even though I was content with hormone therapy. So I kept fighting the judicial system, and The Transgender Legal Education Defense Fund finally heard my pleas and helped me get my real name. The moral of that story is that if you keep trying and keep fighting hard, you’ll come out on top.
Monika: What made that decision to transition so significant for you?
Kendra: It was a difficult process. I transitioned in a men’s penitentiary with over 1,000 men looking over my shoulder at all times. I was literally a woman in a men’s penitentiary, it was terrifying. Some of the men in there hadn’t seen a woman for decades, so it was definitely a challenging process, but it bettered me and my life.
Monika: What kept you going through such a challenging and isolating experience?
Kendra: I finally got to live my truth as authentically as I wanted to be, even if it was terrifying at times. I really had nothing else to lose, no one from the outside was reaching out to me, not my family, not my friends, not my friends from the street whom I thought loved and cared about me. I was truly alone. So I didn’t have anything in this world to lose, but everything to gain by trying to live as a transgender woman.
Monika: During your transition, were there any transgender role models who inspired or guided you in your journey?
Kendra: Caitlyn Jenner, because she’s a strong and independent woman who holds her faith close to her heart, even though she’s been criticized by both the Christian community and the LGBT community. That’s similar to some of my experiences. She’s a role model to me also because she stands up for what she believes in, even if that means standing alone.
Monika: Were there other role models whose courage and resilience influenced you?
Kendra: Kristin Beck is a role model of mine because being the first openly transgender woman in the Navy SEALs shows just how tough she really is. She’s the author of the book Warrior Princess: A U.S. Navy SEAL’s Journey to Coming Out. Media outlets have speculated that because of her, the Department of Defense revisited its policies on transgender people serving openly in the U.S. military. I feel she’s walked a tough road, like me, but still came out on top, just like me.
Monika: What about role models who have taken risks for justice or stood up for what they believed was right?
Kendra: Chelsea Manning, because she was prosecuted for doing what she thought was the right thing, releasing documents to the public out of a sense of duty to others. She did it in the name of love for her country. She’s a transgender woman and an ex-United States Army soldier who released classified United States documents to a whistleblower. She was arrested on espionage charges and was originally set to be released in 2045, but after an executive order pardoned her, she was released in May of 2017.
Monika: Are there any transgender women you admire and respect who have played an important role in your life?
Kendra: Yes, Trudy Kitzmiller, Kayla Warner, Mya Williams, and Tess de Carlo. Trudy is my transgender mom, she’s helped me through it all, and without her, I really don’t know where I’d be right now, probably dead. We may have our ups and downs, but I know that without her, my life wouldn’t be where it is today.
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| With Freddie Lutz, owner of Freddies beach bar, doing her 1st book signing. He supports her dreams, and believes in her. |
Monika: Can you tell me a bit about your connections with the others you mentioned?
Kendra: Mya Williams is like a daughter to me, I never got to have kids, so she’s the closest thing to a real daughter that I have, and I love her to death! I was truly blessed with Tess de Carlo, fate brought us together to write my book, and without her, I’m not sure I would have been able to do it. Kayla Warner is a good friend of mine, and I love her dearly. I asked her to write a little something about me and our relationship for this interview, but she had to decline for a wonderful reason: she was having dinner with her mother as her mother’s daughter for the first time, which is just beautiful!
Monika: What was the most challenging part of coming out as a transgender woman?
Kendra: Being in a men's prison with thousands of men looking over my shoulder at all times. Everyone in that prison could see my transition. There were no secrets in that place. Another hard thing about coming out was that it was already difficult coming out as gay when I was William, so I knew it would be even harder for me to come out as Trans Kendra.
Monika: Within the LGBTQ community, transgender people are often seen as the “T” in the acronym. Do you feel the transgender community is able to have its own voice and advocate for its unique challenges while still being part of the larger LGBTQ movement?
Kendra: I believe that the LGBTQ community is an inclusive community. We need each other, we need each other's support. But we need to realize there's a difference between gender identity and sexual orientation. Being one of the smallest minority groups, we need to stand together to support one another because if we were to break apart, we'd be an even smaller minority group. Plus the LGBTQ community is all about inclusiveness and support, so to break us apart would go against what we stand for.
Monika: How do you feel about the way transgender people and stories have been portrayed in the media, whether in films, newspapers, or books?
Kendra: I can't answer that in the abstract because I've been in the newspapers, the news, and all over the web. I believe that we need to be visible in order for people to understand the transgender community and accept it, because people fear what they don't know or understand. They fear what they haven't seen in their lives.
Monika: What do you think is the role of the transgender community in speaking out and advocating for our rights?
Kendra: We have to stay loud and proud because this is our lives we're talking about. If we don't keep speaking out on our behalf and on behalf of our entire community, we'd be walked on. There are people who really hate us out there, and if we don't call them out, we'll continue to be oppressed and have our rights taken away until we no longer have a voice and can no longer speak out for what is right and just.
Monika: Are you involved in any advocacy or lobbying campaigns? How do these experiences shape your view of political engagement for transgender women?
Kendra: I'm a part of the No H8 Campaign, the Longing for Eden ministry, and the Be Human Not Heartless campaign. As far as politics go, I want to be heavily involved, and I think I'd be good at it because I'm compassionate towards people and I want to do something to improve people's lives or their perspective on life. I want to speak from the heart and touch people with my words, which is rare to see in politicians.
END OF PART 1
All photos: courtesy of Kendra Brill.
© 2025 - Monika Kowalska
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