In a world where the transgender community often finds itself navigating uncharted terrain, it is heartening to meet women like Lisa O’Connor, who not only survived her own transition but chose to transform it into a beacon of support for others. A physician, therapist, and proud founder of Healthy Transitions, LLC, Lisa is a steady and compassionate presence for countless transgender and gender-diverse individuals seeking guidance, affirmation, and care. Born and raised in the vibrant heart of New York City, Lisa brings a blend of sharp intellect and warm humor to everything she does, from her clinical work in endocrinology and psychotherapy to the simple yet profound act of helping someone pick their first outfit or find the courage to come out. Her approach is holistic, deeply human, and grounded in lived experience. Lisa’s journey into womanhood was anything but easy.
Like many of us, she walked through fire, losing family, a job, and nearly her peace of mind. But in the ashes, she found a calling. Her mother’s unexpected embrace became a light in the darkness, one that still shines in Lisa’s practice today, where kindness and knowledge go hand in hand. She’s the kind of woman who understands that beauty isn’t about passing, it’s about presence. That health isn’t just medical, it’s emotional, social, and spiritual. And that freedom for trans people won’t come in a bottle or a scalpel alone, but in the fierce, daily act of living authentically. Today, I have the honor of speaking with this extraordinary woman, part healer, part advocate, part philosopher, and always herself. Please join me in welcoming Lisa O’Connor, a woman whose work, wisdom, and warmth continue to shape lives far beyond the walls of her clinic.
Monika: It’s a real pleasure and honor to speak today with Lisa O’Connor, an American physician, healthcare provider, and therapist who supports the transgender and gender-variant community. Lisa is also the owner of Healthy Transitions and is based in Stirling, New Jersey. Welcome, Lisa!
Lisa: Hiya, Monika! Thanks for having me. Poland is lovely this time of year. It’s only the second time I’ve ever visited.
Monika: Let’s start with a bit of background. How would you introduce yourself?
Lisa: Hmm, well, the usual opening line is that I was born and raised in New York City. Thankfully, your readers will not have to suffer through my Metropolitan New York English accent. By the way, you are very kind for not mocking me.
Monika: Your company is called Healthy Transitions. The word “healthy” really stands out, what does a healthy transition actually involve?
Lisa: This is one of those €64,000 questions. We could talk for hours on this topic. It’s huge. As a matter of fact, it is one of my guiding principles for Healthy Transitions, LLC: healthy and happy.
To get us out of here at a reasonable hour, let’s shoot for the more manageable €1.37 answer. Back in the day, when I first explored transitioning, the concept of “healthy” wasn’t really on the radar. Like many others, I didn’t worry too much about being “healthy.” All I wanted was assistance with the process. I knew it was new ground for the medical community. Nevertheless, I was both shocked and chagrined when the endocrinologist, to whom I was referred, asked me, “OK, what do I do?” That question stuck with me, it was both humbling and empowering at the same time.
Monika: That must have been a revealing moment. How did your medical background help you navigate such uncharted territory?
Lisa: By happy chance, all family physicians are well-versed in endocrinology, and being known as the local go-to family doc for the university gay and lesbian community, I had a lot of experience dealing with the LGB community and their medical needs. I felt comfortable guiding any healthcare provider who was willing to help me and, if needed, listen to my guidance. That experience later shaped how I structured my own practice, supporting others by sharing both clinical knowledge and personal insight.
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| "Back in the day, when I first explored transitioning, the concept of "healthy" wasn’t really on the radar." |
Monika: What inspired you to shape Healthy Transitions, LLC the way you did, and what specific services do you offer to the transgender community?
Lisa: As a direct consequence of the experiences of my own transition, I opted to make Healthy Transitions, LLC a two-fold practice. Today, half my clients are seeking help with hormone therapy. The other half are seeking guidance, counseling, and for some, outright psychotherapy. Fortunately, I am also a certified Cognitive Behavioral Therapist. So, on one hand, half my practice is endocrinology, limited to helping people achieve their gender goals. The other half is counseling. However, another guiding principle of Healthy Transitions, LLC is, “whatever it takes.”
Monika: Your motto “whatever it takes” is powerful. Can you share how that philosophy plays out in the day-to-day work you do with your clients?
Lisa: Yes. When Healthy Transitions first opened, many clients were asking me for help with some very basic and, for the transgender community, some universal issues. Where and how to buy clothes? How best to bind? What about packing and STPs? Oh, sorry, "STP" is packing that allows someone to Stand To Pee. How to come out to family? Work? Identification? Sexual intimacy? And the like. I didn’t know who specialized in these areas, so I used my own experience and that of my clients to help answer these questions. This kind of practical, everyday support became a cornerstone of my work.
Monika: That’s incredibly comprehensive care. How do you make time for all of that within the typical healthcare structure?
Lisa: Since I don’t feel comfortable prescribing hormones in a five-minute appointment, how could I not take the extra time to help someone who earnestly had no clue how New Jersey, New York, Pennsylvania, or whatever state in which they lived, dealt with identification? That’s why today, a simple follow-up appointment is scheduled to last as long as 45 minutes. I believe trans clients deserve the same thoughtful, unhurried attention anyone would want when making life-changing decisions.
Monika: Some argue that while cisgender women gained new freedoms through the invention of the contraceptive pill, transgender women have found a form of liberation through access to cosmetic surgery, no longer feeling trapped by the pressures of “passing.” What are your thoughts on this comparison?
Lisa: I’m not too sure about that. This is another biggie. OK, let’s see where this goes. Some of my happiest, highest-functioning transfeminine clients are the ones most comfortable in their own skin. Some are over six feet tall, that’s two meters for the civilized world, and built like ultra-masculine rugby players. As one said to me, “With a body like this, you think a nose job will help me ‘pass?’” I truly admire the self-acceptance some of them radiate.
Monika: And what about clients who pursue multiple surgeries, do you find their motivations differ?
Lisa: Then there are the clients who, to my eye, look beautiful on day one. Naturally feminine, with lithe bodies, you know, great genetics. I often wonder how anyone could ever see that client as anything other than female. Yet, they feel the need for all kinds of cosmetic surgery, and repeat surgeries. Sure, some have issues with body dysmorphia, but many do not. To be fair, beauty is in the eye of the beholder. I may feel, for them, it’s like gilding a lily. But if they are healthy and happy, who am I to judge? Each client’s journey is deeply personal and shaped by experiences I may never fully understand.
Monika: Do you think the ability to “pass” or “blend” actually leads to greater freedom, or is that freedom still conditional?
Lisa: But to your question, are they free? More liberated than the two-meter-tall rugby player? Is “passing” or, my new preferred term, “blending,” really that important? Hmm, OK, well, here’s where I play my own devil’s advocate. Wow, we really could have a three-day seminar on this topic! OK, here’s one potential example of the importance of passing. Anyone familiar with the United States and all the alt-right lunacy surrounding bathroom laws knows just how dangerous it is to be transgender or genderqueer and not “pass” or “blend.” The murder rate is so high in our community. Life is a lot easier when you have to go to the bathroom and no one stops you for not looking enough like a woman. The reality is, for many, “blending” isn’t about vanity, it’s about survival.
Monika: It’s clear that the topic of “blending” and perceived freedom opens up a much deeper conversation about societal values. How do you personally envision a more inclusive future for gender-diverse individuals?
Lisa: I guess what I’m saying is, I hope the day will come when gender distinctions are no longer important. The singular issue of gender is already so complex, let alone the added layers of introducing gender-expansive people into a society where homophobes and transphobes feel the need for bathroom laws. I figure our emancipation, our freedom, our liberation is so much more complex than cosmetic surgery. I’m guessing you and/or I may get some mail on that answer. To whomever reads this interview, please know I was just musing out loud on this very important and complex issue. We’re all friends here, right? (laughs)
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| Lisa in the army. |
Monika: Shifting gears a bit, can you tell us about your personal journey? When did you begin your transition, and how did the process unfold for you?
Lisa: Great question. That used to be the most commonly asked question when I began publicly speaking on the topic. I guess the easiest and shortest answer would be: when I told the world. You know, changed my name, my attire, told the people at work. That was in 2005. But when I hear that question, I like to think I am still transitioning. My appearance, behaviors, sexuality, you name it, are in a constant state of flux. Maybe evolving? Maybe I am simply gender-fluid? It’s been a deeply personal and continually unfolding process.
Monika: That’s such a powerful perspective. Do you remember when you first began to sense you might be transgender?
Lisa: Another way I get that question is, “When did you begin your transition?” I tell them I’m not entirely sure. Was it when I was five years old and wondering why God made such a mistake? At puberty, when I first questioned my sexuality yet felt I was not gay? The first time I took estrogen? The first time I told someone? My first therapist? The first time I ventured out into public as a woman? The list goes on and on! Looking back, it feels like there were dozens of small beginnings rather than one single moment.
Monika: When you began your transition, whatever definition of transition best fits your experience, were there any transgender individuals you looked up to or found guidance from?
Lisa: None. I was aware some people had somehow done what I only prayed to God for: Christine Jorgensen, Jan Morris, Tula, Renée Richards. But none were role models. They were more like beacons of hope, of what could be.
Monika: And what about today? Are there any transgender women you especially admire or respect now?
Lisa: Too many to list. Hundreds. If I can’t name them all, I won’t name one.
Monika: Many transgender women make profound sacrifices on the path to becoming their true selves. Families can be lost, careers disrupted, and emotional well-being tested. Did you have to pay such a price? What was the most difficult part of your coming out?
Lisa: Yeah, I paid a similar price. Lost my family, my job, my sanity. You name it, I lost it. The hardest thing? Telling my Mom. I was so scared I would disappoint her. I feared going from the golden-haired son who could do no wrong to a social deviant who needed to be locked up. Long story short, she was great. She could have written a book on how a parent can best respond to their child coming out as transgender. It was seamless. We immediately became each other's best friends and confidants. When I first opened Healthy Transitions, LLC, she was happy to volunteer to be my office manager. Clients loved her. More than one brought their own mothers in, simply to meet my Mom. She was great.
Monika: In recent years, we've seen a wave of visibility for trans women in nearly every sphere, from fashion and the arts to science, politics, and business. Some say we’re witnessing a true societal shift. Do you think we’re making real progress, or are we still only scratching the surface?
Lisa: As it is said, “A thousand-mile journey begins with a single step.” I feel the movement is akin to those large marathon races. The starting pistol goes off, but it takes like five minutes before the last runner has crossed the starting line. It’s like that. The starting pistol has been fired, but I feel the last runner is nowhere near crossing the starting line. At least the race has begun. It feels good knowing that.
Monika: While the transgender movement is often grouped within the broader LGBTQ+ umbrella, does it sometimes feel like the unique needs of the trans community get sidelined? How effectively can trans people advocate for their own rights within such a diverse coalition?
Lisa: Absolutely. Many times, that acronym has an “A” in it for advocate. I feel every letter in whatever your preferred acronym is, stands for two distinct things. The first is the obvious, lesbian, gay, bi, trans, queer, etc. The second is the “A” for advocate. We are all advocates for each other. And today, I can see as far as I do because I am standing on the shoulders of those who came before me. It’s a shared legacy that keeps pushing us forward.
Monika: Given that shared history, do you see the transgender community as playing a central role in the broader LGBTQ+ rights movement, both historically and today?
Lisa: You know, as a New Yorker, I am particularly proud of The Stonewall Riot of 1969. We may be the penultimate letter in the abbreviation, but we were first to be arrested at Stonewall. Yeah, we’ve always been there. And we continue to be there, helping marginalized communities, be they LGBTQ+, the homeless, refugees, you name it. As a species, humanity ultimately sinks or swims together. Everyone’s cause is both individual and collective. It reminds me that justice for one group always opens the door for others.
Monika: When it comes to fashion, do you have a personal style or favorite looks? How do you usually choose your outfits, and are there any brands, colors, or trends you particularly like or avoid?
Lisa: Monika, as you can tell by my ripped T-shirt and cut-off jeans, I have set a high fashion standard for myself. (Laughs) Seriously, when I first transitioned, at the office I wore nice women’s business suits and dresses to dinner, black leather and lace on Saturday nights. You know, hubba, hubba! (laughs) Fashion was a big part of expressing my new identity back then, and I loved exploring those styles.
END OF PART 1
All photos: courtesy of Lisa O'Connor.
© 2017 - Monika Kowalska
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