Transgender Transitions

Reflections from the other side

Kathryn J Redman
6 min readNov 14, 2022
Photo by Luke Leung on Unsplash

You can’t hate someone whose story you know.

— Margaret J. Wheatley

I am a Transgender woman.

I completed my legal transition in August of 2021, and my medical transition in May of 2022. I am completely, physically, and legally, a woman. The old man is dead.

First of all, I love how I navigate the world now. I also love how the world mostly responds to me. I can/could never go back. I would rather die before I would face the world again as I did back in the day. (Just to be clear, I am far from suicidal. The prior statement simply reflects how much I love my life now.)

My reason for writing is that I hope to make this a series of stories documenting what it is truly like to live as a transgendered individual. It’s my hope that my story can educate. Prayerfully, maybe some of our politicians will read this before they get tangled up in the next round of hate mongering, misinformation, and disinformation about my community and myself. This is, and will be, a compendium of questions I’ve been asked, over the years, and my response to the questions.

All I ever wanted to accomplish, by transitioning, which I can say is the same for 99.99% of the trans community, is to live my life at peace with myself! Therefore, today, I’m writing about why I chose to transition.

I never ‘chose’ to transition! If anything I chose ‘not’ to transition.

I have been aware of the disconnect between my head, and my heart; my body, and the world from my earliest memories. I asked my mother, probably around the age of 3 or 4, why I was a boy and not a girl. The answer she gave me was “It’s just they way it is.” It wasn’t a satisfactory answer. Oh well, It was my mom, what was I to say?

I’ll admit it wasn’t until the story of Renee Richards broke around the 1976, 1977, time frame that I understood who, and what, I was. Yes, prior to her coming out, I had no way to describe my conundrum. As I learned about what was inside of her, I came to recognize the same thoughts, feelings, and emotions were inside of me. Yet, I was just a teenager; not old enough for emancipation. Oh well. What was I to do?

I was raised a cradle Catholic. As such I was taught bigotry, disgust, revulsion, and hatred for non cis-het lifestyles. Yet, when I left the parochial education system, at the end of my senior year in high school and went on to college, strangely, many of my friends turned out to be gay or lesbian. Yes, there were others besides me that viewed ourselves as cis-het, but we/I, decided that we/I didn’t care about others sexuality or identity. As Pope Francis said, years later; “Who am I to judge?” That said, the risks sure seemed to outweigh the benefits.

After college, I went on to have, what the vast majority would say was, a successful career as an IT architect and change agent, as a husband, as a father. However, what was inside me was always there. Most days it was an irritant, an anxiety, or an anger that was present just under the surface. Days where I had privacy, it could escape in episodes of cross dressing or other purportedly ‘kinky’ and ‘deviant’ behaviors. Generally, it was controlled by my focus on my family; our daughters with their band, volleyball, and other activities; my customers and clients, and alcohol. We all have too much to lose. Why should I turn the world upside down now?

Alas, life moves ahead slowly and relentlessly. Children grow up, move out, and form families of their own. Careers wind down into retirement. Couples, who’ve been together for the majority of their lives do their best to adjust. So my ‘distractions,’ as Caitlyn Jenner describes them, or my ‘coping mechanisms’ as I describe them all eventually faded away. Rats! What do I do now?

In 2018, we were grandparents and great grandparents by a step granddaughter. IBM had decided they were paying me too much money and didn’t need my customers, or I, anymore. I found myself with a ton of time on my hands, a spouse who I loved dearly, and bourbon. The bourbon took hold.

By the summer of 2018, things reached a breaking point. I was drinking way too much. My relationship with my wife, and our daughters, had degenerated into anger and disgust. I was having heart symptoms and given myself Fatty Liver Disease.

Lying in a hospital bed one night, I realized, “I can’t do this anymore.” If I stay on my current path, I’ll lose the relationships that were oh so important to me, and be alone and dead in a few, or several, years. Something had to change. I was at rock bottom, my ‘come to Jesus’ moment.

In my career as an IT change agent, I had learned, and knew, people only willingly accept change is when the pain of changing is less than the pain of the status quo. It always boils down to the ‘devil you know vs. the devil you don’t know.’

That night I understood, I no longer had anything to lose. I could do nothing, and I would lose everything. I could transition, still lose everything, however, at least I’d be at peace with myself.

I didn’t chose to transition. I was out of options. It had become transition or die. The pain of delaying my current inevitable was now greater than the pain of the journey before me.

I cried very hard, and a lot, that night.

Right, wrong, or indifferent; when I had something incredibly major, or difficult, to discuss, I’ve always taken time to write a letter. Most times the letter never got delivered. The letter was, as I learned over my years, the best way I had to get my thoughts in order. One fateful night, about two weeks after I was discharged from the hospital, I spent a teary, frightening, and sleepless night writing out my thoughts to Patty. In that letter, I told her I was trans, (I actually had an initial diagnosis back in the 1993 time frame.) explained what it meant to me, said my intent was to go back into counseling, and complete a full Male to Female transition. I was at rock bottom. I had no other ideas of what to do to survive.

In four pages, I destroyed her world!

I can’t count he number of times, over the next 18/24 months, that we were one wrong word from separation. We fought like cats in dogs. She hit me with all of it: I need to pray; I’ll never be a woman; I’m mentally ill; I’m perverted; her husband is dead. I’ll write about these in future stories.

Finally and truthfully, as I reflect back, I think I always knew that I would reach my breaking point, my transition point. I remember for years, when coming up with an idea, or a purchase, that would appease my girly heart, I would do it. When IBM and Apple struck their corporate partnership agreement, part of the deal enabled IBM employees to buy Apple products at deeply discounted prices. I bought the most girlish Apple Watch I could come up with and stored it for a few years until I came out and accepted myself. Only then did I start wearing it.

As a transgender woman, and a member of the transgender community, I can attest that we are not perverts, nor groomers, nor any of the other names that the bigoted, white supremacist, minority of politicians likes to describe us with. We are simply people who, after years of resistance, finally break down and accept that our only choice is to live as God designed us. Our only choice is to live as transgenders, and yes, other humans that denigrate us be damned!

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Kathryn J Redman

Finally living my life at peace with myself and my world!