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The 5 Biggest Mistakes I’ve Made On My Trans Journey (So Far)

I guess I thought coming out meant throwing out all my “boy” clothes, putting on a dress and heels, some makeup and a wig, and becoming Laverne Cox, Janet Mock, Carmen Carrera, and Munroe Bergdorf the next day. I could not have been more wrong.

Transess isn’t a race or a marathonit’s a slow, long trudge home in the rain, water soaking your jeans and tight T-shirt, filling your socks and shoes, after your ride forgot to pick you up. Though, admittedly, that’s just my cynicism and bitterness talking because, really, the journey is a magical one if you take out unlearning all the social programming, the financial costs, and the threats to your life.

The situation isn’t too good for me right now, but looking around for someone to blame often just leaves me feeling helpless and angry. After my fair share of breakdowns many of which ended with me crying or fuming or both about something I couldn’t find words forI had to recognize that I was setting myself up for failure. Transitioning is not easy for most people, but spare yourself the added pain by avoiding these five beginner mistakes. Though I sound cranky, I promise this is a message sent with love.

Putting myself on dating sites

It’ll be different for me, I told myself. People will like me for who I am, I told myself. Perhaps it was the inflation of my ego, due to the love and support I’d received on my new, female-presenting pictures, but I truly thought I’d be treated like any other woman on these dating sites. Or maybe I was just bored. In hindsight, though, I’m not sure why I thought being treated like any other woman was a good thing, but I digress.

I signed up, wrote a decent bio, and shared some of my favorite new pictures. To my surprise, I received a large number of likes and messages. Despite the fact that many of the messages were sexual and far too forward in nature, I found myself obsessed with the attention. I didn’t care that they were being disrespectful, so long as they were paying attention to me. I felt seen, and even though it wasn’t in the way I wanted, I was at least being seen as a woman (kind of).

We always come down from these ego-highs, however, and I came down hard. When you strip away the horniness and sensuality that you feel flirting with people online, you can see it for what it is. I was being stereotyped. I was being fetishized. I was receiving the kind of messages that trans women are sick of getting.

What’s worse, is that I was ultimately too afraid to meet even the guys that were genuine and understanding. I couldn’t swim yet I was jumping into the deep end. It’s one thing for me to show people photos online, beautified with Snapchat filters that made my skin look perfect and my $100 wig look a bit more expensive. It’s another thing to see and talk to someone in person (dysphoria is a bitch). It was in those panicked moments that I realized I hadn’t given myself any time to grow. I neglected the process before it could even begin, thinking that these apps would help me become a woman overnight, when, really, all they did was waste mine and other people’s time.

I still use them, despite knowing it’s a mistake, because I can’t help myself. I’m great at understanding my problems but not so good at doing anything to fix them.

Letting cis-men judge my womanhood

You’d think using dating apps to avoid dealing with my emotions and real life problems was bad enough. No. I had to go and let men judge my womanhood. MEN! I found myself feeling like a woman when men would compliment me and tell me how pretty I was. It made me feel authentic despite the very real fact that some men will say absolutely anything to get what they want.

I not only cared about their validation, I craved it. When a guy would chat with me, normally, not mentioning anything about my transness, I’d not so cooly or casually ask if they read my bio (wherein the first sentence discloses that I’m trans). In a way, it was almost like I was trying to pre-emptively apologize for it and like I was making sure they were ok with me despite this “bad” thing about me.

I’m still learning how to talk with men this way, and maybe I out myself because I want to know I’m safe with them before I commit to anything. My nightmare is being discovered and attacked by someone who swallowed the bigot Kool-Aid that tells them I’m a deviant whose sole purposes in life are to prey on “innocent” straight men and attack their women in public restrooms. But the truth is, when you let men become the gatekeepers to your womanhood, you’ll never win.

Not setting realistic goals for hair and makeup skills

Not all girls wear makeup or spend an exorbitant amount of time on their hair. However, the ones that do are often taught these skills from a young age, which gives them time to develop these skills throughout adolescence into adulthood. Trans women, on the other hand, typically aren’t afforded this opportunity. I, for example, never learned how to do makeup or my hair, aside from shampooing and conditioning, of course. So when I was tasked with doing my own makeup and styling my own wig, I felt defeated and pathetic as I stood staring at my mirror, unsure of even where to begin.

I guess through Instagram and YouTube, I’ve come to see and internalize a certain image of trans womanhood. There are few women who look like me women who are just beginning their journey. I feel like I’m the “before” picture. Society only cares about the “after” picture.

I’m learning every day and blessed to have a partner who is a cosmetologist but ultimately it’s up to me to learn. And I can’t learn as long as I expect myself to be able to beat a full, perfect mug on my first few attempts.

Letting people misgender me and call me by my dead name

Maybe I’m weak. Maybe I’m not brave. I think these things every time I let someone misgender me and/or call me by my dead name. I want to own my transness, boldly and confidently, because deep down I know there is absolutely nothing wrong with me and that I am entitled to fair and courteous treatment. But still, I let it happen.

When people apologize for calling me by my dead name, I often brush it off, feeling terribly as they apologize profusely. I don’t want to make them feel bad or feel uncomfortable around me. Perhaps I think it’s me that’s asking a lot, that I’m selfish for taking a person these people knew and changing them, even though I know I was never really that person.

The more I let people get by, the worse I feel about it. I keep thinking that, a few months in, I should be at the point where I can stand up for myself. But I don’t. I keep everyone else comfortable while I feel uncomfortable, and in the end, something has to give.

Either I have to demand to be recognized as I am, consistently and without fail, or I will continue to be called whatever people want.

Not building community with other trans women

I wonder why I feel so lost as I continuously talk to cis people about my trans identity. I figure if I explain it enough they’ll understand. But they don’t; they can’t. I know my agoraphobia is partially to blame for why I don’t go out and build community more often but I’m not too proud to admit that the other part is probably my own internalized homonormativity and transphobia.

I hate myself and my trans identity and hate other people who make me think of this part of myself. I see visibly trans people (which, what does that even mean anyways?) and I avoid them like RuPaul avoids genuine accountability. Maybe I don’t want to be associated with transness. I want to kill who I was and just start life over as a cis-woman. I know that’ll never happen but I want it anyway.

As crazy as I feel, I think I’m not the only trans person to have felt this way. I’d know for sure if I actually went out and got to know other trans people. Sometimes we need people who understand our experiences, not just people who can empathize with them. I know that’s what I need right now.

While I’m still working on rectifying these many mistakes, I can at least report that I went to a trans support group a week ago. And while I’m still a walking disaster with bad makeup and a clockable wig, I felt beautiful, safe, and loved in that space. I don’t believe “it gets better,” but I do believe that it gets less difficult when you’re surrounded by people who understand you. I’m a slow moving train puttering to its destination, but I am on my way.