Lately, I’ve been asking myself something big: could I actually transition at work? Not in theory. Not someday. But now?
And for a long time, that question filled me with anxiety. Like, stomach-in-knots, heart-racing-at-the-thought kind of anxiety. But recently, I’ve felt more okay with the idea. Not fully ready, maybe—but definitely more hopeful. And even though I’m not making any immediate moves, I want to talk about it. Because for a while, just thinking about transition at work felt impossible.
💜 This is a small part of my personal journey. Want the full story of how I figured it all out? I broke it all down here:
Crossdresser vs Transgender: How I Finally Figured Out Who I Am
Why I Was Scared to Transition at Work
The truth is, I’m the sole provider in our family. My wife stays home with the kids—and she’s incredible at it. But because of that, the pressure to keep a roof over our heads and food on the table? That falls entirely on me.
And that’s been the biggest reason I’ve held back.
It’s not that I hate my job. It’s actually a good job. But if I lost it? That would be devastating. Not just for me—but for all of us. And that’s the part I haven’t been willing to risk.
The Difference Living as Michelle Made
I spent an entire week recently living as Michelle—outside of work, of course. And the emotional difference? Immediate. I felt more aligned, more present, more real in my own skin.
And it made me want that feeling everywhere—even at work. Not because I hate my current life, but because I finally saw what it could feel like to be fully me.
What I Found While Researching Transition at Work
So, I started looking into it.
At first, I told myself I was doing it because my therapist asked me to—but truthfully, that was a lie. I was doing it because I needed to know if this was even possible.
I started with our employee handbook. There wasn’t much mention of gender identity, but the dress code? It’s based on professionalism, not gender. As long as I meet basic standards, I can present however I want.
But here’s the important part: I didn’t stop there.
I spoke with HR. And if you’re thinking about transitioning at work too? Please—talk to your HR department. They were helpful, honest, and fully supportive. That conversation gave me a kind of peace I didn’t expect.
Getting Support From My Boss and Coworkers
I reached out to my department head, just to get a sense of how she’d feel. I was bracing for awkwardness or hesitation. What I got instead? Full support. She told me she just wants me to be happy coming to work every day—regardless of how I present.
That felt like such a relief.
Next, I came out to two coworkers I really admire. I needed to know if I might come off as mocking or disrespectful—like I was performing femininity instead of just being myself. It’s a silly fear, maybe, but real. They were both kind. Thoughtful. Supportive. And they had no idea I’d already been presenting more femme.
Others Have Transitioned at Work—Why Not Me?
There’s another trans person in my department already. And several more in the broader organization.
And honestly? My job is pretty quiet. I’m not customer-facing. I don’t interact with many people during the day. I do my work and go home. So if I did start to transition at work, it could be quiet, subtle, and low-drama—just the way I like it.
How I’ve Been Testing Transition at Work
Am I already dipping my toes in?
Oh yeah.
I wear shapewear under my clothes almost daily. I do light makeup. I’ve started using more of a head voice when I speak, especially since I don’t talk a lot at work anyway. And I’m working on feminine posture and walk—even if it doesn’t always go as planned.
These are little things. But they help. They make me feel like I’m not just waiting—I’m moving.
Could I Transition at Work? Honestly… Maybe.
When I first sat down to write this post, I thought the answer would be a hard no. But the more I looked into our policies, talked to HR, opened up to coworkers, and got real with myself? The more that no started shifting into a maybe—and now a quiet but growing yes.
It’s not guaranteed. Nothing ever is.
But I feel more supported than I thought I’d be. And that makes all the difference.
Final Thoughts on Transitioning at Work
If you’ve been wondering if you could transition at work—I get it. I really do. The fear, the what-ifs, the risk—it’s all real. But so is the potential. And the freedom.
You don’t have to decide today. But even asking the question matters.
Have you considered transitioning at work?
What helped you feel safe—or what’s holding you back?
I’d love to hear your story. 💬
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