Coming Out As Trans — Life, Work, and Everywhere In-between

Kyler Middleton
13 min readNov 18, 2021

Hey all!

So if you follow me you know I’m heavily focused on making DevOps and automation simple and easy. I like to dive deep into technical topics — that’s my niche! And I love to teach it! Today’s post isn’t about a technical topic, rather it’s about my personal journey of coming out as trans at work, so please skip if that isn’t of interest to you! :)

Second and last note before we dive in — this is relatively personal. It won’t be explicit — I’m not going to talk about genitals or sex, or any of the things the media or political pundits fixate on. I’m going to share a story of self-discovery, vulnerability, and ultimately, knowing myself better than I ever have before.

And also what it means to me, my partner, my friends and family, and my workplace, to share such a personal journey with them.

Cracking the Egg

I am a late-realizer of who I am inside — some people know their entire lives that something isn’t right, but I was only clear on that in retrospect. In the trans community, realizing that your insides don’t match your outsides is referred to as “cracking your egg.”

My story of cracking my own egg is as common as it is silly — I was out with friends, and were playing around with Snapchat filters. There’s one that switches faces with your friends, there’s one that makes you a muffin, there’s one that shows what you’d look like as a different gender.

When I saw mine I felt a bowstring twang inside myself and a wave of feelings rushed over me. My eyes welled up and my partner was alarmed I was having an anxiety attack or something, and pulled me aside. In a promising omen for the future of our relationship, I told her truthfully, “Something powerful happened in me when I saw that photo.”

That transparency and tight connection has helped our marriage improve and become stronger through change and sometimes social adversity, rather than growing apart, as some relationships do in similar situations.

Am I Sure? — Looking Back

I waited a few weeks, talked to my partner more about what had happened, what it meant (if anything), and processed my own feelings.

I grew up in a rural part of the mid-western US. Men are cowboys, strong, somewhat emotionless foundations for others. Women are soft, emotionally intelligent family centers. They handle the social obligations in a pairing, run the family, and in return, get to express themselves freely with colorful clothes and displays of emotions.

I was born male (trans folks call this AMAB, or Assigned Male At Birth), so it was assumed my gender (social role) matched my sex (physical attributes). For most people it does, but there is a minority where it doesn’t. (Interestingly, the percent of people that are transgender is about the same amount who are left-handed!)

Being AMAB, I knew implicitly that I wasn’t allowed to be soft and warm, wasn’t allowed to express myself, was supposed to focus on work, build a family, and close off any weakness and vulnerability.

I tried.

I tried, but it never quite fit. I’m an emotive, empathetic person. I like to talk about feelings and ideas, I like to encourage and exude warmth. Throughout my K-12 I was told many times that I was gay, which made no sense to me — I liked women! I just didn’t fit an archetype of what male meant, and as good as US public school is in the midwest, it didn’t cover gender monitories, so I didn’t know what “trans” was. I just knew I was kinda feminine. That was okay — we’re all just spirits controlling these bodies anyway, right?

But still, this idea that my outsides didn’t match the newly cracked egg (yolk?) inside myself persisted, so I started therapy.

Working Through Therapy

In a similar vein that men should not have emotions, I also grew up with the idea that therapy was for wealthy people, or for “soft” people — those that weren’t capable of withstanding the rigors of hard work and living in the area that I grew up in.

Therapists existed, but they were primarily focused (in my experience) for people to work through their challenges being Christian, or to normalize their beings into an acceptable cookie-cutter for their particular church or family.

But this looming choice of mine continued to persist, and I knew in my heart that this would affect myself, my partner, my work, and my entire life in a real way. I knew that some people would find out this one fact about me and write me off entirely, discounting my entire existence and life because of it. That is a scary, scary thought, and one I spent a lot of late nights worrying about.

But with some coaching and support from my unwaveringly accepting and kind partner, I decided to work through these feelings with a therapist.

Therapy felt revelatory — I talked openly like I wasn’t expected or allowed to throughout my life, with anyone except my partner and sometimes my immediate family.

From the get-go, I was upfront with my therapist. I didn’t start with a conclusion, I started with a goal — to be more authentic. To connect with people in a stronger way, to help me see people more truly, and be seen in return.

The biggest changes felt epic and huge, though I’m sure they’re the common fodder of most therapy:

  • Trust yourself. You know what’s right. If you set aside your prejudices and look for truth, you’ll find it.
  • You own your life. This one was huge for me. I don’t know where I got this idea that I needed (NEEDED) to live my life to avoid making others uncomfortable, but that was always of critical importance. When living for what others see only, it’s hard to be… well, anything. How can you establish who you are if your primary goal is first to be what they expect? It led to a chameleon-like state where I wasn’t able to be authentic. I realized this need wasn’t healthy, and was keeping me from being more authentic in my relationships.
  • You’ll lose some people. When you share who you are, unapologetically, some people won’t like it. You have to recognize and make peace that some people will find out this one fact and will never, ever like or recognize me. I’ll flatten into a stereotype and be discarded. Making peace with this was both necessary and incredibly powerful. When you accept this, you can be yourself without fear. It’s incredible.

With those lessons (and many others) in mind, I saw that this was the right choice for me.

A lot of looking back on phrases, life choices, even my selection of life-partner, fit neatly into this narrative. It’s as if a small, hidden part of my mind had been influencing my choices.

I’m still mad at that small part. Couldn’t it have been louder, earlier? But I think I had to grow before I could let it. I’m still working to forgive myself for this.

I decided to move forward. I worked with a doctor to start hormones, which work at an incredibly slow pace, and started preparing. There was a silly amount of work to do. Should I learn makeup? Style my hair differently? Buy new clothes? How will I tell people? When should I tell people? Who should I tell first? Will my work care? Will I be discriminated against? Will my wife? Will my daughter?

I’m an engineer by trade and by quirk — I’m a rote person, I’m structured and stubborn, and I like to plan things. My coworkers reading this can attest! :)

And yet, this isn’t something I can plan well — I can’t see all the way to a new life, I can only see a few feet into the darkness. I had to learn to trust myself, and take a step, and see how it felt. If it felt right for me, felt authentic, I took another step. Slowly, those steps started showing me the path.

That path felt like finding my authentic self. When I’m authentic, I can connect with others. I can help them, I can lead them. With the support of my wife, I started coming out.

Coming Out

Before I started this journey, I knew that LGBTQ+ folks “came out.” I thought it was a one-time event. Like, you’d post on facebook, “Hey, I’m gay!” and everyone would hit “Like”, and you’d be done.

That turned out to be kind of a naive idea — coming out happens continually, in each circle you run in. Coming out to your partner, your children, your immediate family, your extended family, your close friends, your more nebulous friends, your manager, your work’s HR, your coworkers, should I announce this to my new friend? And on and on.

I spent a huge amount of time and effort on what my therapist calls “hypotheticalizing.” Which just means walking through a hypothetical conversation with someone, or a group, over and over. How will they react? Will they accept me? Will they put up with me? Will they reject me and react with bigotry and hatred? All of those are possible, and the unhappy possibility of losing people I care about made these hypothetical conversations exhausting and stressful.

I hoped to work through them in the same way we engineer products — make a theory, test it, make a theory, test it, until you find “the perfect plan.” But life doesn’t work that way. The only way to get these over with was to start, and let the chips fall where they may. I gathered my confidence and began.

My sister and her husband had the best response. They said “we don’t care” in the most wonderful way. There was no hedging, no probing. Just acceptance and love.

A long-time friend had another great response. She told me that based on her spouse’s great reaction, she knew that her kids would have a supportive father if they ever came to a similar revelation. That one touched me, and still does. She found the great in the situation, and helped make the scary worth it.

There was also the bad, of course. Two important people in my life said that they knew for sure that all trans people knew their entire life, so since I hadn’t told them before, that meant I had been lying, had been dishonest to my core, for the duration of our relationship. That crushed me. I was so scared since the onset that me changing any presentation about myself would lead others to think I’m dishonest, and inauthentic. They tried to convince my partner to leave me, to find a “real husband.” I ended my relationship with them, a relationship that had lasted over 10 years.

I had other less traumatic but still strange encounters. Some friends peppered me or my partner with questions, like “so are you a lesbian now?” or to my partner, “So you’re gay now, huh?” Some folks felt strongly that we should be put into boxes, so we could be organized, and possibly so stereotypes could be applied. But minority identities resist cataloging, especially when it comes to human identities. We shut down the convo.

Almost everyone was supportive and accepting. I lost some friends, but I decided, the ones I lost were the right ones. The ones I kept grew closer.

Coming Out At Work

Coming out at work is scary!

First of all, I mostly kept work and life separate. I like to shut my computer at the end of my workday and focus on my partner, my hobbies, my family.

Second of all, I work in IT in a position of authority — both as a leader of humans, and as an operations administrator with a great deal of permissions in many networks. I had a huge amount of anxiety that any of the people I interacted with would have the same reaction as the poorest reaction in my personal life — they’d see me as inherently dishonest, and that could jeopardize both my people leadership positions, as well as my job itself, given that it relies on a strong, inherent trust in my judgement and forth-rightness.

I came out to my manager first. I was the first person who’d done that with him, and he wasn’t sure what to say. He asked for permission to talk to HR, which I granted. He promised to learn more and help me every step of the way.

A few weeks later I had a meeting with my manager and an HR rep — the “gender specialist” at this large company. I sometimes (maybe often!) don’t appreciate working for a large organization (10k+ employees), but having an HR specialist with experience in this stuff is an amazing, wonderful situation to be in. She had helped many others come out, and was able to provide guidance to my manager, as well as documentation, support, and resources that could help me in this, ahem, transition.

I had a month-long leave coming up to have my first child (!), and I thought about having my manager announce this change while I was out. That’d permit all the scuttlebutt to die down before I returned. I’d read this was a good idea online, but eventually decided against it. I’m a strong communicator, and I’d like to control the narrative. (Also I think this advice is more tailored to an in-person office, which I don’t work at).

I wrote up a positive (and meme-containing) email. I painted this transition truthfully, and authentically, which felt wonderful and also very scary.

Revealing who you are truly is a very vulnerable place to be in!

I iterated over this email many times with my partner, my manager, and the HR specialist. I decided to send it before my month-long leave, with the idea that I could communicate this out, answer any Qs, then go on my leave and let the idea soak in for people.

One great piece of feedback I got at this stage was to explain why I’m sharing this personal life change at work. Past generations built a firewall between their work personas and their personal lives. I added the following section to my email, and had many responses from people calling it out as an impactful part of what I expressed. We all crave purpose, and authenticity is part of connecting with coworkers or with anyone.

Part of my email to my workmates, coming out as transgender

It was also important to share this change at work because I was asking for something — people to use different pronouns for me. Even that small tax I wanted to help minimize by fully explaining what it meant to me.

Here’s a link to the full email. If you need to come out I hope this can serve as a template or informs how you write it! If it does, please share that with me :)

Hitting Send

I was a mess before sending this email. If this went poorly, my role and job was over. If it went well, how I was viewed was potentially forever changed regardless. I ignored many emails.

I hit send. About 50 people were informed in seconds, with instructions at the bottom to forward to anyone I had missed. I also encouraged folks to reply-all with encouraging words, and very much hoped a few people would!

What happened next I still don’t believe. Over the course of the next few days, I received many dozens of positive responses. Here are only a small selection of anonymized responses:

I also posted in an #allyship room we maintain on our slack about my journey, and got a great deal of support and acceptance. I cried happy tears many times over the next few days. I’d be trying to focus (and not really succeeding), and I’d get another positive response.


The best I expected from anyone in a workplace was luke-warm tolerance. The idea that standing out was wrong had been long ingrained in me, and I’m still working to get that out.

Transitioning is long-lived. I keep hoping that I’ll be done soon, but rebuilding an identity, recontextualizing relationships, memories, friendships, can take time and effort, on both sides.

I am still surprised and overjoyed when people use the correct pronouns for me. I really shouldn’t be overjoyed, but I smile each time it happens.

Revealing my true self, and having people accept and welcome me, has been a tremendously scary, impactful journey, and I am so thankful to anyone that has been a part of it. I feel seen, and I hope that I’m able to use my privilege and skills to blaze a path forward for anyone less privileged than I am, to follow along.

Good luck out there!
Kyler (she/her)



Kyler Middleton

DevNetSecOps, DevRel, cloud security chick. I will teach you, it’s unavoidable. She/Her 🏳️‍🌈🏳️‍🌈, INFJ-A, support the EFF!