Hey everyone, I’ve been reflecting on how tough it can be to let go of those old parts of ourselves—like, we’d rather stick with the uncomfortable stuff we know than dive into the unknown, even if it might feel way better.
You know that vibe: “We’ve grown accustomed, and we’d rather stay with the uncomfortable known than the comfortable unknown.”
At 65, this really resonates with me during my transition from male to female. I’ve made so much progress, feeling more authentic every day, but I still cling to remnants of my old male self, especially around longtime business clients and friends who’ve only known me that way.
I never felt the need to tell them about my transition—it just didn’t seem essential for our connections. With social media, zoom technology, it was easy to play the part.
Sure, on a zoom with me showing from shoulders up, I get comments from other people “wow, you look really good. What are you doing?” And I’d always shrug it off and just say I eat right and exercise and good genes (all true), but deep inside I knew I was hiding it. I never weighed my hands for fear of showing my nails either.
But get this: I’m heading to LA for a business trip soon, with these folks covering my flight, hotel, and meals. Super nice, right? Except they don’t know about my change. I was thinking about slipping back into “guy mode” for the trip to avoid awkwardness, but is that even doable? I’ve had breast augmentation. You may have boticed 😂. Hiding “the girls” sounds rather impossible and emotionally draining. And honestly, do I want to? Not at all—it’d feel so ubtrue to myself.
This whole concept reminds me of a story I saw about an Olympic downhill skier who was gay but kept it hidden from everyone. He said that secret was like a constant weight holding him back from being his best.
Once he let it go and told people, that burden lifted, he felt free to be his true self, and his scores just skyrocketed. That’s exactly how I imagine it could feel for me—and maybe for a lot of us in similar spots. Not that there won’t be some fallout or unintended fallout. That’s expected. But holding on is be hindering more than helping.
In my case, I think I’m ready to throw caution to the wind and just say (in so many words), “Surprise! Here I am—take it or leave it.” I’m not saying everyone should do this right now for themselves or at all; you have to do what’s right for you. But man, the idea of that freedom is exciting.
Gwen 💕






2 Responses
Gwen,
As you’re probably alraedy aware I also faced that decision , albeit not with work colleagues . Interestingly I came out in a slightly odd way to my art group in my old town . I was painting a small ( real ) railway station set in the coutryside most of which is now gone apart from the crossing and signal box . The left side of the painting was an empty platform , so I added the correct style bench but then I wanted to put a figure sitting on it , so I dressed with appropriate items and placed a bench in my garden with identical lighting and took a selection of pictures. While painting the scene in the art room my tutor ( David ) liked the idea but he began to question who the lady was , when we broke for coffee I said , ” you’ve sussed me , haven’t you ? ” The fact is he hadn’t so when I told him it was me in the pictures his jaw dropped to the floor . After that he couldn’t quite get his head round the fact I’d painted myself as a female in my painting , obviously the cat was now out of the bag so the story soon got round the rest of the art group . I asked David if he would object if I attended as Teresa , he wasn’t sure how to answer , the problem was he was paid to run the group and it was only viable with ten or more , so if other artists weren’t happy and stopped attending the Art Centre could close the group down . I decided to miss a week and instead meet them all at the coffee break as Teresa , it couldn’t have gone any better , they all wanted me to start the new term as Teresa , David was delighted .
After that I never really looked back , so when I moved to a new art group in my new home town It was so much easier to go as Teresa which has never created a problem . I just kept building my confidence , I thought less and less about my male side so now 99.9% of the time he doesn’t exist it’s not even a problem with some very old friends who knew me for years as a guy .
If I was facing your situation with that trip consider what is the worse that can happen , what is the worse fear ? Personally when I’ve had those fears most if not all are inside our own heads , how much are other people really bothered ?
The other point to consider is you’re not the only one that dresses , you may even find some of your colleagues might come out to you , that’s happened a couple of times to me , if might just open the door for someone else .
You always look amazing my dear