Interview with Alana Nicole Sholar

There are people who move through the world with a kind of quiet gravity, their stories unfolding not with loud declarations but with a steady, unwavering truth. Alana Nicole Sholar is one of those rare voices, soft-spoken, yet impossible to ignore. Born and raised in Kentucky, she grew up in a deeply religious, working-class environment that made it difficult to speak her truth, let alone live it. But she persisted. With time, reflection, and an inner strength forged through years of self-discovery, Alana emerged as an author, activist, and advocate, not just for herself, but for countless others navigating the complex terrain of gender identity. In 2012, Alana published her groundbreaking memoir, Hung in the Middle: A Journey of Gender Discovery, which explores her life growing up as a transgender person assigned male at birth. 

 

The book resonates with warmth, candor, and the kind of wisdom that can only come from lived experience. It became more than just a personal testimony, it became a beacon of understanding for readers who may have felt alone in their own transitions or who simply wanted to better understand someone else's. Beyond the page, Alana is a vibrant presence. Whether she’s speaking at LGBTQ+ events, engaging with readers, or sharing tender moments with her loving partner, Bobbie Thompson, she brings a sense of calm authenticity that invites others to feel safe, seen, and validated. Together, the two have become known for their openness, compassion, and unwavering support for the transgender community. Alana reminds us that our journeys don’t have to be rushed or linear. That it’s okay to take your time, to question, to pause, to begin again. That visibility can be an act of love, and survival. Today, I have the honor of speaking with Alana about her story, her advocacy, and the lessons she continues to learn and share along the way.

 

Monika: Today, I have the heartfelt pleasure and profound honor of sitting down with Alana Nicole Sholar, an inspiring transgender activist and writer from the rolling hills of Kentucky. Alana is the author of Hung in the Middle: A Journey of Gender Discovery, a deeply moving memoir that chronicles her path toward self-understanding and acceptance. With grace, courage, and Southern candor, she has opened doors for so many through her advocacy and storytelling. Alana, welcome, and thank you for being here with me today. 

Alana: Thank you so much, Monika. It’s truly a joy to be here with you. I’ve followed your work and the thoughtful conversations you bring into the world, so I’m genuinely honored to share this space with you today.

Monika: Let’s begin with a glimpse into your professional journey. How would you describe your career so far and the experiences that have shaped it?

Alana: My newfound career has been really exciting. I have learned so much by writing Hung in the Middle: A Journey of Gender Discovery … all of it good. When I set out to write my story, it was in hopes of bringing help to others, so imagine the surprise I got as others opened up and shared their journey. Many have given me an idea or notion that had never entered my way of thinking. Hung in the Middle has sold around the world, which also surprised me. I had hoped it might, I just never expected it to happen as fast as it did. Many people have helped me accomplish as much as I have … including you … thank you. 

 

Alana's biography.

 

Monika: What sparked the idea to write your memoir? Was there a particular moment when you realized your life story needed to be shared with the world? 

Alana: I often told people stories about my past, you know, the wild side of my life: drinking, drugs, playing music in bars, fast cars, fast horses, and a confused sex life. Lots of folks said I needed to write my stories down. However, the one thing I never told anyone was that I had a secret. Many of the risky things I did in life were an attempt to keep my secret hidden. I tried to write my story a number of times, but without being able to tell my entire story, it was impossible for me to tell any of my stories. After I finally faced what I’d been running from all my life, I came out as transgender. Just a few years after coming out, the factory where I worked closed its doors and I lost my job, which gave me lots of free time on my hands. I just sat down and started writing.

Monika: Looking back at your life story, which parts do you believe could serve as guidance or reassurance for other transgender women who are planning their own transitions?

Alana: I hope that one thing others are helped with is by knowing they are not alone. I think things are getting better than when I was young. Younger generations are more open and accepting toward trans persons … at least that’s been my experience.

Monika: When you first began your transition, did you have anyone you could look up to or turn to for guidance and support, someone who helped you see what was possible?

Alana: The role models I had were friends I made locally, friendships I built through the Transgender Support Group, a part of the Gay Lesbian Services Organization (GLSO) in Lexington, Kentucky. There were several members in our support group, and I thought the world of each of them. However, there were three that I hung out with the most: Kellin, Cassie, and Kaillie. Kellin became the head of our support group for a number of years. She and I enjoyed many outings together, we grew very close. Kellin was there for me when I was diagnosed with HIV. Her friendship is valuable to me. Cassie later became, and to this day still is, the fearless leader of the support group. She is another person I spent a good amount of time with.

Monika: It sounds like these women played a meaningful role in your journey. Could you share a bit more about what their support meant to you, especially during the more difficult times? 

Alana: Cassie became a shopping and movie partner for a while. She was also a major role player in my finding the right and perfect wigs. And Kaillie, there is no way I can ever thank Kaillie enough for all she has done for me over the years. When I was diagnosed with HIV, Kaillie would make an hour-long drive, one way, to get me out of the house. Kaillie is a hero in her own right for the kindness that she shows to many each and every day. Kaillie does these things without thought, it just comes naturally to her. She is what I call the real deal. Her kindness helped me through a very difficult time in my life. Nowadays, there are so many role models out there for young people. However, never forget that the best role models you can find are sometimes in your own backyard.

 

Book signing and speaking engagement
Joseph Beth Booksellers, Lexington, KY.

 

Monika: What was the most difficult part of coming out and embracing your true self?

Alana: The hardest thing for me personally was being able to accept myself. Even after I came out as transgender, people around me seemed to accept me more easily than I was able to accept myself. Sometimes I just hated myself. I still live my life ‘hung in the middle’ of two genders and still have to be careful about not liking myself at times. I attribute much of the depression I deal with to my difficulty in being happy with myself.

Monika: How do you feel transgender stories and characters have been portrayed so far in films, newspapers, and books?

Alana: I think it’s getting better and believe it will continue to do so, especially as more and more people begin to see us as we truly are: human beings. The news is something that I rarely watch, it’s just too negative. Bobbie and I try to keep a positive attitude, and watching the news can make that difficult. If I felt I could get the truth from a news source, I might feel differently, but nowadays it all feels so slanted. At times, it feels like maybe they try to brainwash people into their way of thinking.

Monika: Would you say 2013 was a breakthrough year for the transgender community in the United States?

Alana: I think we got a lot of positive exposure in 2013 here in the USA. Hopefully, such positive exposure will lead to better things for trans persons, like equal rights, protection laws, and insurance companies covering surgeries, just like any other tax-paying individual.

Monika: What’s your perspective on the current status of transgender women in American society?

Alana: I feel like we still have a long way to go, but I have to say our situation is good compared to some other countries. I am thankful that we have the recognition and acceptance we do have and that it continues to get better daily.

Monika: Are you involved in politics or lobbying efforts? Do you believe transgender women can influence political change?

Alana: I feel transgender women can make a big difference in politics. This isn’t a role I fit into very well, though. I do what I can by way of voting, but I am not politically savvy. I have tried a number of times to become involved, but politics just makes me crazy. When I see everything happening in politics, I can get frustrated, depressed, and even go as far as becoming enraged. It’s rare that I voice my political opinion other than voting for the person I feel is right for the position.

 

Interview for ewhpress (YouTube)

 

Monika: Is there anyone in the American transgender community today whose activism reminds you of what Harvey Milk achieved in the 1960s and 70s for gay rights?

Alana: Harvey Milk was a politician, and I’m not aware of anyone in the political arena who compares. However, there are some trans persons who I believe are bringing positive attention to our community, Chaz Bono, Janet Mock, Carmen Carrera, and Laverne Cox are names that come to mind. It’s always been hard for me to compare one person’s actions and good deeds with those of another. Everyone’s contribution is as unique as the person themselves. And I appreciate those everyday persons who are making a difference in their families, their neighborhoods, and their workplaces. Those people are not in the spotlight like the ones I just named, but it is the actions of those persons who are making the greatest contributions to our community.
Monika: Could you share your thoughts on the role love has played in your life? 

Alana: Love has been very important to me, although it took me the greatest part of my life to learn how to love, myself or someone else. If it wasn’t for Bobbie’s love and continued support, I most likely would not be doing this interview because, without her support, I would never have written Hung in the Middle. I sat down and wrote my memories, it was Bobbie who put those memories together, resulting in my memoir. Bobbie supports me professionally by handling all my business arrangements and attending my speaking and book-signing events. She supports me personally by going to all of my doctor’s appointments with me and by us simply sharing our lives together. My family as a whole has always been there for me, which is the best way any family can show you love, and that’s a real blessing.

Monika: Do you enjoy fashion? What kinds of outfits do you usually wear? Are there any special styles, colors, or trends you favor?

Alana: I’m a country girl, so I wear jeans a lot, I love my boots and jeans. I don’t follow trends or colors; I just wear what I like, trendy or not. There was a time when I first came out that I wanted to get all dressed up, especially when I’d go out to a gay bar, but with age, I’ve gotten more into comfort. The only time I wear a dress these days is when attending a book-signing or speaking event. Once in a while, I might wear a dress to go out to eat, but most of the time I like my jeans and boots. Don’t get me wrong, I still like to look good; it’s just that I don’t mess with the high heels and short skirts as much as I once did.

Monika: What are your thoughts on transgender beauty pageants?

Alana: They are great. I feel this is a major way to show people that we are so much more than what some perceive us to be. I think such pageants allow others to see that we are, in fact, women and should be treated as such.

On Transition Radio Show (YouTube)

Monika: Are you currently working on any new writing projects or creative endeavors?

Alana: I have a second book, a work of fiction, available in e-book format on Amazon.com. It’s trans-erotica and my first attempt at writing fiction, or erotica. It was lots of fun to write. The title is The Horn-Dog Bar and Grill. It was a fun story to write, and I hope people have fun reading it. I’m hoping to write other fiction books, but I’ll just have to wait and see what the future brings.

Monika: Do you have plans for any upcoming memoirs or personal projects? 

Alana: I do plan on writing another memoir. I want to write about my experience of living as a female full-time after my transition is complete, but that will require a couple of surgeries first, namely facial feminization and breast implants. I haven’t made a decision about any additional surgeries yet, but I will face that when the time comes. I hope to entitle my next memoir With Head Held High. Right now, Bobbie and I are putting our focus on getting her book published. She says it’s ‘her side of our story’ and a companion to my book. The title of her book is My HUSBAND Looks Better in Lingerie Than I Do … DAMN IT. We have a target release date of February 14, 2014.

Monika: Having gone through your own transition, what advice would you give to transgender women who are currently struggling with gender dysphoria?

Alana: I would beg them to please seek out the help of a supportive, informed therapist. Everyone goes through various experiences in life where the help of a therapist is valuable, and we as trans women face more stressful situations than most people. My therapist is a big part of my book because it was with her help that I began to learn how to accept myself. Without her help, I’m not sure I could be where I am today.

Monika: Alana, thank you so much for sharing your story with me today. 

Alana: Thank you for allowing me to share, Monika. Also, I wish to thank you for all that you do in making us a stronger community. You are a blessing.

All the photos: courtesy of Alana Nicole Sholar.

© 2014 - Monika Kowalska

  

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