Transgender People: Everything I Ever Wanted to Know About Them But Was Afraid to Ask

A Deep Dive into Transgender Psychology, Biology and Politics

Martin D. Hirsch
Curated Newsletters
15 min readMar 8, 2024

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Image licensed from Shutterstock.

About 50 years ago, in one of my first reporting assignments, I was sent to interview a middle-aged college professor who had created an art exhibit illustrating what it’s like to transition to being a “transsexual,” the term that was used back then. In those days, trans people were pure curiosity, guests you might catch on a late-night talk show.

What a difference a half-century makes. Trans people are out in the open, characters on popular TV shows, and … the targets of a vicious campaign by religious conservatives who view them — despite their only making up about 1.5% of young adults in America — as a mortal threat to our country.

The Washington Post has reported that, just since January of 2023, state legislatures have introduced nearly 600 anti-trans bills. Legislative targets include imposed bans or limits on transgender athletes’ sports participation at the K-12 or collegiate level, policies barring gender-affirming medical care, and restrictions on transgender people’s use of public restrooms. Just last month, a 16-year-old non-binary girl in Oklahoma died after being assaulted in her school’s bathroom.

As a 72-year-old straight white man, I have no quarrel with transgender people. But I know far less about them than the other letters in the LBGTQIA+ rainbow. And I want to know more.

So, when I recently attended a guest presentation by a transgender woman at a university class I was observing, I went up to her afterward to ask if she’d speak with me about her life, transition, and challenges. She agreed.

Alaina Kupec, 54 — a successful pharmaceutical company executive before and after her transition — spoke with me both in person and in correspondence over the past few months — revealing a personal journey rich in honesty and insight. The following extended interview has been edited for length and clarity.

Martin D. Hirsch: Judging by your bio — you were North Carolina State University’s Navy ROTC Honor Graduate in 1992, went on to serve as a U.S. Naval Intelligence Officer with distinction, and then you got married, had children, and were working as a successful pharma executive — you seemed to be doing pretty well in your life as a man. You waited until you were 43 to become transgender. That’s a rather head-spinning evolution. When did you get your first inkling that you weren’t comfortable in your gender and what was it like to go through what must have been many years of agonizing internal conflict?

Alaina Kupec: First, let me correct something in your question. You stated that I was doing well in my “life as a man.” I would say I was doing well in my life presenting as a man. Let me try to explain the difference. My brain has always been that of a woman. Inside, I have always been what you see me as today. My body was incongruent with my brain until my physical transition. So I have always been transgender; it wasn’t something I became at 43.

As far as when I first felt uncomfortable with my birth gender, I can remember as early as 6 or 7 years old knowing something wasn’t right. I used to sneak into my mother’s closet when she wasn’t there to try on her clothes, shoes and makeup. I had no frame of reference for why I felt the way I did, only that I felt feminine and wanted to appear that way. Yet I was also conscious that my body had boy parts, and that came with intense shame, denial and confusion. I felt that something must be broken in me. And, this being the mid-1970s, I had no one I could talk to or look to as an example.

I went through puberty equally confused, not being able to understand why I wasn’t developing physically on the outside as a woman. I know how strange that sounds. Imagine how it felt for me, living through my teens feeling that my body was supposed to be starting to menstruate and develop breasts, but being locked inside the walls of a male jail cell.

(Author’s Note: The scientific name for the conflict Alaina felt is “gender dysphoria.” It is a real phenomenon that appears to be genetically based. This article in the journal Nature explains a study about the phenomenon.)

Alaina Kupec, 54, transitioned 11 years ago. She provided this photo of herself taken last summer during a visit to Lake Como, Italy.
Known before her transition as Herbert Kupec, Alaina provided this photo from Herbert’s stint as a decorated Naval officer, pictured here in 1994 off the strait of Gibraltar in the Mediterranean sea.

The Broad Gender Continuum

MDH: How did labels affect you as you were growing up — the cultural expectation that you were a boy and had to act in certain ways considered masculine, or a girl and had to act feminine?

AK: Gender expression is a continuum, from hypermasculine to hyper-feminine and all points in between. Same for sexual orientation, which ranges from gay/lesbian to straight and bi. We all have a need to process information in a way that helps us to break down and understand the complexity around us, so binaries are a way we try and do that. But in the case of gender and sexuality, this is a false construct. You can have effeminate males who are heterosexual. You can have hyperfeminine females who are lesbians. And the opposites are true. In my case, I tried to conform to the gender assigned me at birth, which led to significant shame and guilt for feeling feminine.

MDH: Did you experience any “continuum” in your romantic relationships throughout your life? Were you attracted to males or females as a young person? Did you go through any gay or bi periods in your life?

AK: I have never, ever been attracted to men in any way. I repressed my gender expression my whole life, but always knew 1,000% that my sexual orientation was being attracted to women. And for me that has never changed. On the advice of friends, after my transition I went on one date with a man while I was separated from my now ex-wife. And he was very kind, very nice, very professional. But it was so ick ick ick for me! His hair, his touch, his smell, all those things were a total turn-off.

MDH: What about other groups within the overall LGBTQ+ community? How do you and other trans people get along with them?

AK: Many gay men do NOT support transgender women, for a number of complex reasons. I think a large part is just a lack of understanding about who we are and how we’re different from them. But as a woman who has lost white male privilege, I see the world 180 degrees differently than I did 11 years ago, when I still presented as a man. I think the other part of it is that we in the trans community are such a small percentage of the overall community, and the least common. And we’ve only been more visible in the past 10 years, so many in the LGBT community are just now getting to know us.

MDH: You said that as a trans woman, you’d lost your “white male privilege.” Can you elaborate on that?

AK: Before my transition, I was completely blind to white male privilege, and I think my experience now as a woman is helping to give me some appreciation for what many white men are feeling in today’s world. Many see diversity and equality as a threat to them and the historical place they have held in the workplace and society. If others get equality, they may fear it means less opportunity for them. They are not able to see the advantages they have inherently received from their race/gender status.

The other thing I have experienced, vividly, is how I am treated now by male colleagues versus when I presented as a man. I worked for the same leader at Pfizer before and after my gender transition. I had the same role, the same peer colleagues, and the same direct reports. My leader was a white man, and when it came time for my performance review the first year after my transition, I was told that I needed to “tone it down” a little in leadership team meetings. I had been a top performer before and after transition, always sharing best practices and helping my peers. Which was seen as a strength as a man, but in a negative way when presenting as a woman. My reaction was disbelief. And I have continued to hear this from time to time from other white male senior leaders in my workplace. I was privately told by a senior leader at my present company that I came across too confident in meetings and that I would be better served saying less. Those things never happened to me presenting as a man.

Time to Tell Mom and Dad

MDH: How did your parents react to your being transgender — both at first and over time?

AK: I will forever remember the day I came out to my parents. It brings me to tears just thinking about it. I was raised Catholic and still consider myself to be, despite the U.S. Catholic Church’s stance. I was prepared to lose my relationship with both of them when I came out. But I knew that if I didn’t make that choice, what I would likely lose was my life. And I prayed that God would guide me through my journey with strength and that people would see the real me and come to accept me. But hoping and praying was all I had, because in most cases, losing everything is what most people experience. It is why 40% of homeless youth are LGBT. It is why the historical rate of attempted suicide is close to 50% for people who are transgender. So imagine doing it at 43, while leading a pharmaceutical sales team in the southeastern part of the U.S., in the Bible Belt.

But when I came out to my parents at their dinner table, they cried with me, gave me the biggest hug I have ever had in my life, and accepted me from the very moment I told them. And that, to me, the unconditional love and support of parents, is what reinforces my faith in God. They showed me through love and actions what it means to be Christian. Not judging others, not casting stones, but rather showing me, their child, unconditional love and support.

MDH: So the first big ordeal was coming out to your parents. And the next was actually going through with your decision. Can you please try to explain the intense psychological and physical process you had to go through — how long it takes and what happens in the various stages?

AK: A physical transition takes a long time, often years. I think that people have a misperception that it’s like flipping a switch. But gender expression and dressing feminine are very different from a physical transition.

For everyone, it starts with mental health counseling. It is critical to get care from a counselor trained in dealing with gender dysphoria, who can also properly work through the differential diagnosis to ensure that the person is experiencing gender dysphoria and not another mental health condition. Only after receiving continual care, typically, for a year, will someone start hormone therapy, and only after letters from the mental health expert documenting the condition.

While that is taking place, someone like me — who has undergone puberty and has facial hair — it involved getting over 250 hours of electrolysis to remove all the permanent hair from my face. This is where a needle is inserted into each follicle, electrically charged to kill the follicle, then manually plucked. It is the only permanent means of removing facial hair, and typically costs $100 an hour.

At the same time, voice training takes place. Since I had undergone puberty, my voice had deepened. I had to retrain my voice to speak from the top of my vocal cords, which took countless hours of practice and repetition, also learning to inflect in ways that women do. Again, that takes time and costs a minimum of a thousand dollars, often more, and is not covered by insurance.

Then when it is time to start the hormone therapy, there are three things that typically take place. First, suppressing any naturally occurring testosterone with an oral medicine. In my case my body was producing hardly any prior to my transition, which is a reason my body was misaligned with my brain. While suppressing testosterone, estrogen is then added to bring estrogen levels up to that of a woman.

Then there are the surgeries, which is what most people focus in on. There is a process to feminize the face by softening the male features that were developed because of the testosterone at puberty. That testosterone drove facial hair, deepening of the voice, along with forehead and brow development, and very different characteristics than I would have had if I had never gone through puberty. Most insurance doesn’t cover these surgeries either.

The estrogen drives breast development, but typically those later in life don’t get the full development they would have had they gone through puberty in their teens. So many women like me get breast augmentation.

And lastly, the one most people seem to think is the only thing we get done is the bottom surgery. This called a vaginoplasty — where a female vagina is created by a procedure inverting penile tissue.

There is a huge outcry in this country today about teens receiving puberty blockers to pause their puberty. Had I been able to take those, it would have saved me thousands of dollars in procedures and prevented most of my surgeries. They are truly surgery-sparing drugs, and reversible. Once the puberty blocker is stopped, someone will progress through puberty. All they do is hit pause and allow for the person to get to the age of consent for when they can get the surgeries they need.

Learning to Present as a Woman

MDH: Talk a bit about your transition beyond the surgery that made your body — the external you — congruent with how you felt inside. What did you do to make yourself present more as a female, as a woman?

AK: Well, I bought a wig and women’s clothes and learned how to put on makeup. And I will never forget looking back at myself and, for the first time ever, seeing who I was on the inside looking back at me. That was a seminal point. And then I bought breast prostheses and experienced for the first time the sense that my body started feeling normal. Carrying the weight in my chest in that way instantly reconciled with my sense of my self in my brain. It was at that very moment that my body first started to feel “normal” to me.

Transitioning to a New Romantic Life

MDH: What is your current relationship and family life like?

AK: When I made the decision to live my authentic self, I made peace with the fact that I would likely spend the rest of my life alone. And then, along came my angel. She was born on Christmas Day. I met her two months into my physical transition, and she asked me to marry her two years later.

My three now adult sons were 10, 12, and 14 when I came out to them. And they are in my life today and have been most of the past 10 years. There are things that they went through after my ex-wife and I got divorced and she remarried, and those things temporarily strained our relationship, but only for a short period of time. They have shown me love, empathy and compassion throughout.

Alaina Kupec (center) with her wife and three sons. Alaina provided the photo.

How to Deal with Children on the Subject of Gender Nonconformity

MDH: I’ve talked to parents with young kids — children between 5 and 9 years old — who’ve told me their children are being taught about gender identity issues, and they’re angry about it and have complained to school officials. What are your thoughts on how and when parents and teachers should tackle gender issues with children?

AK: If it is taking place, then I too think it is wrong. I think that these are topics that should be between a child, their parents, and if appropriate, medical professionals who are experts in these areas. These are not things that should be taking place in school. Now that is my personal opinion, which may not be what others like me think. But that is my perspective.

Gender Politics

MDH: Shortly after your transition, 11 years ago at the age of 43, you were prompted to become a trans activist when the state of North Carolina, where you’d attended college and lived at the time, introduced HB2, the so-called “bathroom bill.” You were filmed and featured in the first nationally aired transgender ad, showing you being denied access to a women’s public bathroom. Today you head an organization called Gender Research Advisory Council + Education, or GRACE, for short. What are your organization’s objectives, whose opinions are you trying hardest to influence and why?

AK: My wife calls me the accidental activist, which is probably accurate. I live my life peacefully, where no one around me on a daily basis knows my gender history. They only see me as a woman.

I started GRACE because I want to change the narrative of how the world sees people like me. We are your neighbor, your co-worker, your friend. We exist all around you, and have for a long, long time, and we never bothered you. We became more visible to you in 2014, when shows like Orange is the New Black came out that had a trans character. Then Caitlyn Jenner transitioned. And right after that the Supreme Court ruled for marriage equality. So the timing of our visibility made us targets. Which is what we see today. Efforts to erase us from society, by denying us gender-affirming care, not just children, but even me as an adult in Florida.

This is what GRACE is fighting. We advocate for people like me who just want to exist peacefully and quietly and aren’t hurting anyone.

MDH: What about the issue of transgender women competing in women’s sports. Can you understand why so many people think this is unfair to biological women athletes?

AK: This is an extremely tough question. I don’t think there is one answer on this due to the complexity of different sports, different ages, and different genders. I think every sport has to take a look at this from a medical perspective and many of the governing bodies have done that work. So let’s leave it to the governing bodies, the medical experts, and keep politics from making blanket decisions that are ill-informed and potentially harmful.

Takeaways for Us Straight Folks

For live-and-let-live-minded straight folks like me and many others who may be reading this, here are the key insights I took away from my conversation with Alaina Kupec:

1. The LGBTQIA+ community is not one big happy family. Within the community, the same issues of lack of understanding, differing political priorities, and entrenched thinking exist in the society at large. Gays don’t always see eye to eye with trans people, who may be at odds with drag queens, etc.

2. Although the intense spotlight on gender fluidity among young people may increase levels of curiosity and experimentation, true transgender individuals like Alaina Kupec really do experience terrible “dysphoria” — the intense feeling of being trapped in a body that conflicts with their sense of their sex in their minds. Moreover, they suffer the added stress, guilt, and shame of feeling constantly that they are lying to the world by “presenting” themselves as someone fundamentally different from who they are. And many have no one to talk to about this traumatic situation they find themselves in 24/7.

3. Transgender women like Alaina Kupec may possess the most unique perspective of all on how men and women are treated differently in the workplace. Having experienced how co-workers and bosses interact with them and evaluate their performance as both men and women, who else has experienced both first-hand and lived to tell about it?

4. Once straight people gain a clearer understanding of what transgender people are all about — just as we’ve come to understand and accept gay and lesbian friends in our lives — much common ground will emerge to unite us. However, we still may disagree, hopefully agreeably, on some thorny issues, such as whether transgender women should be allowed to compete in men’s sports and what the best age and approach is for dealing with transgender children.

If you’re interested in finding out more about the Gender Research Advisory Council + Education (GRACE), check out its website at this link www.grace-now.org

For further reading on this subject, check out these books:

She’s Not There: A Life in Two Genders, by Jennifer Finney Boylan

Becoming a Visible Man, by Jamison Green

Helping Your Transgender Teen: A Guide for Parents, by Irwin Krieger

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Martin D. Hirsch
Martin D. Hirsch

Written by Martin D. Hirsch

Lapsed singer-songwriter, 35-year accidental company man, citizen of The Woodstock Nation, avid essayist, occasional poet, aspiring author, dogged evolutionary.

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