Caisie Breen, a remarkable transgender writer and the author of the compelling biographical memoir Songbyrd: Becoming She (2016). Caisie’s journey is a powerful testament to resilience, authenticity, and love, proving that the path to self-realization can be both challenging and deeply rewarding. At 61 years old, she has lived a life full of experience, having been married to the same devoted woman for over 36 years, raising two adult sons, and managing a small plumbing and electrical service company in Portland, Oregon. Caisie’s story is not just about her transition, it is about embracing who you truly are, even when the world expects something else. Her decision to write a memoir stemmed from a recommendation often given to transgender people early in their journey: journaling as a tool for self-discovery. For Caisie, this advice became a transformative practice, capturing the complex emotions, challenges, and triumphs she faced while navigating life as her authentic self. One of the most insightful aspects of her memoir addresses the question that many trans women face, especially those transitioning later in life: “Do I pass?” Caisie recalls the early days of her transition, when she wore women’s slacks and tops and struggled to find the confidence to present fully as herself in public. Her honesty and humor shine as she describes her anxieties and the unwavering support of her wife, Brenda, emphasizing that true courage often requires stepping boldly into visibility, even when it feels uncomfortable.
But Caisie’s journey also highlights the emotional realities beyond self-expression. Transitioning does not occur in isolation, it ripples through the lives of loved ones. She shares how her wife experienced grief for the loss of the man she had known for decades, underscoring the importance of empathy and communication in maintaining strong relationships during such profound change. For Caisie, having the full support of her partner was not just beneficial, it was essential. Caisie began her transition at 55, after years of suppressing her gender identity. Even in her later years, she found inspiration from role models like Christine Jorgensen and, later, author Jenny Boylan, whose guidance and writings provided invaluable insights as Caisie crafted her own memoir. Her reflections reveal that authenticity is not bound by age and that seeking guidance from others who have walked similar paths can provide clarity and encouragement. Beyond her personal journey, Caisie is thoughtful about the broader transgender experience. While she chooses to stay away from politics, she recognizes the growing visibility of trans individuals in media, literature, and society, noting that progress is being made and that transgender women can make meaningful contributions to shaping public understanding. Her take on fashion, beauty pageants, and the importance of love adds further depth to her story, reflecting a life lived fully and intentionally.
Currently, Caisie is working on a sequel to her memoir, Bit’s & Pieces, continuing to share her experiences and insights with readers. Her advice to transgender girls struggling with gender dysphoria is simple but profound: patience with yourself and others. This interview offers a rare glimpse into the life of a woman who has navigated decades of personal and social challenges with courage, humor, and grace. Caisie Breen’s story is a reminder that embracing authenticity, nurturing love, and supporting one another are the keys to a fulfilling and meaningful life.
Monika: Today, I have the pleasure and honor of speaking with Caisie Breen, a transgender writer and the author of the biographical memoir Songbyrd: Becoming She (2016). Hello, Caisie!
Caisie: Hello, Monika. Thank you for taking the time to interview me. I’m excited to share my experiences, and I hope they can offer some insight or encouragement to others. Life has been a fascinating journey, and writing about it has been both therapeutic and empowering.
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| Available via Amazon. |
Monika: Could you tell us a little about yourself and your life before and after your transition?
Caisie: I’m 61 years old and have been married to the same lovely woman for over 36 years. We have two adult sons and are owners of a small plumbing and electrical service company in Portland, Oregon. My family has been a tremendous source of support, and our business has given me a sense of purpose beyond my personal journey. Balancing work, family, and self-discovery has been challenging at times, but it has also been incredibly rewarding.
Monika: What inspired you to write your memoir, and how did you begin the process?
Caisie: Frankly, I think it’s one of the standard recommendations given to transgender people by our therapists early on, as a way to help us transition. I got this advice years ago and immediately began keeping journals. Writing allowed me to process my feelings and track my progress in a way that nothing else could. Over time, those journals became the foundation for my memoir, helping me to articulate experiences I had never fully understood before.
Monika: From your personal journey, which experiences or lessons do you think could be most helpful for other transgender women?
Caisie: Wow! Read my book. There are so many things. But if I had to pick a couple, I’ll start with the “Do I pass?” phase. This is especially relevant for those of us who wait until later in life to transition. When I first came out, my hair was still short, and I wasn’t comfortable wearing dresses in public yet. I was more androgynous, wearing women’s slacks and tops. And the crazy thing was, I was always asking Brenda, “Do I pass?”, “Are those people staring?” Hell, no I didn’t pass, and of course, they were staring.
My sweet Brenda always played it down, though. But it was true! So, for those who don’t want to stand out and feel like a freak (like I did early on), wear that dress. Like they say, paint or get off the ladder. The process of learning to present yourself confidently, even in small steps, is vital. It’s about finding joy and authenticity in who you are, rather than seeking approval from others. Confidence is a muscle; it grows stronger the more you practice living authentically. Embracing small victories along the way can make the journey less overwhelming.
Monika: How did your transition affect the relationships in your life, particularly with those closest to you?
Caisie: This is big: as wonderful as it feels to finally become authentic, you must realize that someone will be mourning the loss of the old you, and that’s totally legit. For me, Brenda had been married to the male, Bill Casey, for 30 years, and I was well into my transition before I fully understood her loss. We need to be sensitive to those we love and understand their pain. Transitioning can affect relationships in unexpected ways, and acknowledging the emotions of those around us can help maintain trust and connection. It’s important to give loved ones space to process their feelings without guilt or judgment. Open communication and patience can help sustain these important bonds over time.
Monika: How important was support from your partner during your transition?
Caisie: On this note, and I may be the lone ranger here, I would never have made such a transition without the full support of my wife. My book goes into it well. Having a supportive partner is invaluable, but equally important is developing inner strength and self-compassion to navigate the journey. Brenda’s unwavering encouragement allowed me to take risks I might not have taken alone. I also learned that self-love and resilience are essential tools in living a fulfilled and authentic life.
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| With Jenny Boylan. |
Monika: At what age did you begin your transition into living as a woman, and how challenging was the process for you?
Caisie: I was somewhat of an odd duck here too. My gender had been suppressed so long and so hard that it took two other people saying something to get me to finally understand it. I was 55. The process was emotionally intense, but it was also liberating to finally acknowledge my truth. Looking back, I realize that patience and self-compassion were essential to navigating such a profound life change.
Monika: During the early stages of your transition, did you have any transgender role models or figures who inspired you?
Caisie: My first heroine was Christine Jorgensen. I first read about her, then saw the movie about her. This was way before I knew about my own gender issues. Her courage and visibility inspired me to believe that living authentically was possible. She showed me that being true to oneself can make a lasting impact, even decades later.
Monika: Are there any transgender women you admire today, whose work or life has influenced you?
Caisie: About a year after coming out, I heard about Jenny Boylan and became a big fan of her writings. I was especially fond of her book I’m Looking Through You. I was just beginning my memoir, and when I found out that Jenny was visiting the West Coast, I flew down to San Francisco to meet her. She gave me some priceless advice regarding my memoir, which I followed to the letter. Meeting her reinforced the value of mentorship and community, and it reminded me that connecting with others can provide both guidance and encouragement. Her generosity and insight have stayed with me ever since.
Monika: Looking back, what was the most difficult aspect of coming out to those around you?
Caisie: For me, it was the broken relationships I didn’t see coming. I knew there might be a few casualties, but the ones who dissed me were very much unexpected. It was a painful lesson in human nature and the complexity of love and loyalty. Still, those challenges taught me resilience and the importance of surrounding myself with supportive, understanding people.
Monika: Transgender rights are often discussed alongside the broader LGBT movement. From your perspective, is the transgender community able to advocate effectively for its own issues within the larger LGBT framework?
Caisie: Yes. I don’t get involved in politics anymore, so I won’t elaborate further other than to say, if we want it to happen and are willing to do the legwork, anything is possible. Progress requires persistence and a willingness to speak up when it counts. It also depends on building coalitions and finding allies who understand the unique challenges transgender people face.
Monika: How do you feel about the way transgender people are represented in the media, including news stories, films, and literature?
Caisie: I think things are rapidly improving. There is more visibility now, and transgender stories are becoming more nuanced and authentic. Representation matters because it helps society understand our experiences and challenges. I’m hopeful that this positive trend will continue and expand across different platforms and cultures.
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| The past and presence. |
Monika: Do you personally participate in advocacy or lobbying efforts, and do you think transgender women can have an impact in politics?
Caisie: I stay away from politics, but of course, women are making a difference. Transgender women, in particular, can bring unique perspectives and lived experiences that enrich public discourse. Even small contributions can inspire change and help create a more inclusive society. It’s about showing up and using whatever influence we have to make a positive impact.
Monika: Are you interested in fashion? What types of clothing do you usually wear, and do you have favorite designers, colors, or trends?
Caisie: I’m not really into fancy fashion. I buy most of my clothes online. I particularly like the Liz Claiborne line at JC Penney’s, and pastel pink is my favorite color. Fashion, for me, is more about comfort and personal expression than following trends. I enjoy finding pieces that make me feel confident and authentic in my daily life.
Monika: What are your thoughts on transgender beauty pageants? Some critics argue that these competitions emphasize youth and physical appearance.
Caisie: I have no problem whatsoever with them. I believe these pageants can celebrate confidence, self-expression, and achievement, rather than just appearance. They provide a platform for transgender women to showcase talent and personality, which can be empowering. I also think they help increase visibility and normalize diverse representations of beauty in society.
Monika: How significant is love in your life, and how has it influenced your journey?
Caisie: Love is the engine that makes life work. It has been the foundation of my transition and the glue that has held my family together through change. Love teaches patience, empathy, and resilience, and it motivates us to be our best selves. Without love, navigating challenges would feel far more isolating and daunting.
Monika: Are you currently working on any new projects or creative endeavors?
Caisie: Yes. I’m writing a sequel to my book called Bit’s & Pieces. This project allows me to reflect on new experiences since the first memoir and share more lessons learned along the way. Writing continues to be a source of growth and self-expression for me. I hope it will inspire others who are navigating their own journeys.
Monika: What advice would you give to transgender girls who are struggling with gender dysphoria?
Caisie: Patience with yourself and others. Accept that the journey is not always linear, and it’s okay to take small steps at your own pace. Developing self-compassion and seeking supportive communities can make the process more manageable. Remember that your identity is valid, and living authentically is worth every challenge along the way.
Monika: Caisie, thank you so much for sharing your story and insights with us today!
All the photos: courtesy of Caisie Breen.
© 2017 - Monika Kowalska
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