10 Things I Wish I’d Known When I Started My Transition by Annika Penelope

Exactly two years ago, I sat apprehensively in the reception area of the public health clinic in San Francisco’s Castro neighborhood, waiting for my name to be called. If all went according to plan, I would leave that evening with my first prescriptions for estradiol and spironolactone — day 1 on hormones. I had just come from work, and because only a handful of my colleagues knew about my transition, I was still presenting as a boy (albeit an androgynous one wearing gold eye shadow). I remember looking around the room at the other trans girls sitting nearby. I couldn’t wait to be just like them — to have people see me as my true gender and to finally start feeling comfortable in my body.

It was hard to believe that I had been closeted only two months earlier, and yet here I was, about to embrace the part of myself that I had been ashamed of for nearly all my life. I was ready. Since coming out, I had pored through several radical gender books, watched transition videos on YouTube and researched the hormones I was about to take. I knew what to expect in the weeks and months ahead.


Two years and 4,860 pills later, I now realize how little I actually understood back then. There were so many aspects of transitioning and being treated like a woman in society that I was totally unprepared for. And today I’d like to share 10 lessons that I wish I had known in February 2011.

(Note: This advice is based on my own personal experience as a queer, femme, white, upper-middle-class trans girl with “passing privilege,” so some of it might not be applicable to you.)

1. Brace yourself for beauty culture.

This is especially true for my fellow femme girls, and there’s a reason it’s #1 on my list. Before I started presenting as female, I had no idea just how toxic beauty culture is in this country. Women are constantly inundated with airbrushed images and messages aiming to tear down our self-esteem and make us feel inadequate. Fashion magazines and the beauty industry make billions every year by exploiting these insecurities with the promise that if we only try harder to be prettier, we too can be happy.

As a trans girl, beauty culture can be especially difficult to navigate, because most of us have haven’t been exposed to it very long. Our cis partners and friends have been dealing with it since middle school (if not earlier), and many have had years to develop effective coping strategies, so we DMAB (“designated male at birth”) ladies have to make up for lost time, and on top of that, cissexist standards of beauty add another way for us to feel insecure.

It helps to maintain a sense of perspective. Many trans girls, including me, have a habit of romanticizing the cisgender experience. A month or two into my transition, I told my girlfriend that I couldn’t wait until I could look in the mirror and see a pretty girl staring back at me. “You realize that’s never going to happen, right?” was her response. “You’re going to look at your reflection and feel unsatisfied — just like every other woman.” And it’s true: Even the most gorgeous of my friends can list a dozen things she’d change about her appearance. So the next time you’re feeling unattractive, don’t blame yourself; blame capitalism and a beauty culture designed to make you feel that way.

2. Say goodbye to male privilege.

If, like me, you presented as a normative guy before transitioning, you probably didn’t realize just how many privileges you were about to give up. I took so many little things for granted, like being able to walk outside or go to a bar without random men feeling the need to comment on my appearance. Sexual harassment is such a routine thing now that I can’t even remember what life was like without it.

You’ll probably also notice that people take you less seriously at work because of your gender and presentation. You’ll have to be twice as assertive as you were before in order to get people to pay attention to your contributions, and you’ll possibly be labeled a “bitch” for doing so.

3. People will surprise you.

Coming out as trans* is a great way to find out who your true friends are, and it’s not always the people you’d first suspect. In my experience, if someone is a fundamentally good person, they will almost always be accepting, despite any religious or political misinformation about trans* people they may have learned. It’s a lot harder to otherize being trans* when you know a trans* person personally. So try to give people the benefit of the doubt when coming out to them; you’ll probably be pleasantly surprised.

4. Prepare for (micro)aggressions.

I grew up in a mostly white, conservative suburb where my family was considered “middle-class” because we didn’t have a house on the water or a yacht. In other words, I lived in such a privileged bubble that I had never even heard of microaggressions until I started experiencing them after coming out. If, like me, you were presenting as a heternormative white boy before transitioning, these can seem a little jarring at first, but it’s something that nearly everyone but straight, white cis men have to deal with on a regular basis. So what are microaggressions, exactly? In my case, it’s every time a well-intentioned friend posts an article about a trans* person on my wall or remarks on my physical changes since the last time they saw me, or every time someone asks if my girlfriend and I are sisters (even if we’re holding hands). It’s the little interactions that happen every day that remind you that you are “different” in some way.

(Unfortunately, many trans* people, especially trans women of color, face more than just microaggressions. They are often subjected to discrimination, violence and institutional hostility. I realize that I am incredibly privileged, and in no way am I trying to diminish the struggles of others, but microaggressions are still unpleasant and something that I was not prepared for.)

5. Go to therapy.

Seriously, you should go to therapy. I don’t think it should be required to “prove” your gender before starting hormones, but it’s something that I’d recommend for every person going through transition. It’s an incredibly emotional time, full of triumphs and setbacks and too many feelings to process all by yourself, so take care of your mental health by discussing them with a therapist. I didn’t start seeing one until more than seven months into my transition, and in hindsight I think that waiting as long as I did was a mistake.

6. Pursue other interests.

Transitioning is such a monumental undertaking that it’s easy to let it consume all the other aspects of your life if you’re not careful. That’s why it’s important to maintain other hobbies and interests during this time. Make time to read books that have nothing to do with gender, listen to music, learn a new language, go for a walk, you name it. The important thing is to take a break from thinking about being trans*, even for an hour or two. You’ll start to drive yourself crazy after a while if you don’t.

7. Take a deep breath and be patient.

Hormones are incredible, but they take time to work their magic. You’re not going to notice results overnight. When I first started HRT, I couldn’t wait for the weeks and months to go by. I looked forward to each new dose, because it meant that I was one step closer to feeling comfortable in my own body. I fantasized about ways to fast-forward the next couple of years so that I could finally start enjoying life as my true self. But in constantly looking to the future, I often neglected all the amazing and wonderful things happening around me. I found it hard to simply be in the moment.

My girlfriend and I have recently started practicing mindfulness meditation, and it’s been a really useful tool to help me stay present. I’d recommend it to anyone looking to slow time down and experience life in the moment. A little anticipation can be a good thing, but our life will pass us by if we’re only focused on what lies ahead.

8. Save money.

Transitioning is really expensive. Currently only a handful of insurance companies offer trans*-inclusive health care benefits, which means that many people have to pay for medications, lab tests and doctor’s visits out of pocket. Laser hair removal and electrolysis are also quite pricey and are never covered by insurance, because they are considered “cosmetic” procedures. Changing your legal name and gender in California will set you back at least another $500. And buying an entirely new wardrobe isn’t cheap, either. Bottom line: Start saving now. Your future self will thank you for it.

9. Don’t expect transitioning to solve all your problems.

When I was still closeted, I often blamed every unpleasant experience or emotion on the fact that I had to pretend to be a boy. “One day,” I would tell myself, “I’ll be able to finally be myself, and I’ll be pretty and carefree and never have to deal with this again.” And it’s true that transitioning has made a lot of things better. I connect on a much deeper level with my girlfriend and other people. I’m a kinder and more empathetic person. Little things like painting my nails and getting to express myself through fashion make my days more colorful and enjoyable. I’m so much happier now that I’m no longer hiding who I really am.

But transitioning is not a panacea; it won’t solve all your problems. If you were prone to anxiety before coming out, you’ll probably still have to deal with it afterwards. I still sometimes get in stupid arguments with my girlfriend for no good reason, just like I did two years ago. I’m still addicted to caffeine, and I sometimes forget to turn the lights off when I leave my apartment in the morning. At some point in my transition, I came to terms with the fact that living as my true gender wouldn’t magically fix everything. And it felt really good to let go of that impossible expectation.

10. You do you.

Most trans* people spend years pretending to be someone we aren’t in order to please others: our parents, our friends, our classmates or society in general. And most of us make ourselves miserable because of it. With each passing day, it gets harder for me to remember what it was like to interact with a world that perceived me as a boy, but I’ll never forget how exhausting it felt to be cast as the wrong character in a seemingly never-ending play.

Before coming out as trans*, I never allowed myself to fully relax. I constantly policed my gender presentation and mannerisms to make sure that I wouldn’t raise suspicion. I was terrified that someone would learn the truth about my gender. But one thing that transitioning has taught me is that life is too short to worry about what others think of you. There are more than 7 billion people on this planet, and some of them are inevitably going to disapprove of you and your life choices. For me, the decision is simple: I’d rather face the possibility of rejection then spend another minute in the closet.

Most people don’t ever get the chance to spontaneously and completely reinvent themselves, but trans* people do. Take advantage of this opportunity by being the most authentic you that you can be, and don’t worry about trying to conform to society’s expectations of how someone like you is “supposed to” look or act. If you’re a trans girl who enjoys rugby and hates dresses, don’t let anyone try to deny the validity of your gender. If you’re a trans guy who loves sparkles and makeup, own it. And if you’re trans* but don’t feel comfortable in either binary category of “male” or “female,” resist the pressure to pick one. Be proud of who you are, and don’t be afraid to show it. You deserve to live an authentic life.

* * * * *


So there you have it, 10 things that I wish I’d learned before embarking on the incredible adventure of the past two years. There are many others that didn’t make the list, such as realizing that girls can sometimes be just as gross as guys. (I thought the transition would mean an end to unpleasant public bathrooms, but I was wrong.) I’m undoubtedly still learning; I don’t claim to have everything figured out at this point. But my two-year anniversary on hormones seems like the perfect time to begin the next chapter of my life, a chapter that focuses less on my gender and the fact that I was DMAB.

See more at the Huffington Post.

2 thoughts on “10 Things I Wish I’d Known When I Started My Transition by Annika Penelope

  1. I didn’t know I was trans. I was directed by my primary care Doc to a Therapist who I quickly discovered to be a Certified Sex Therapist who dealt not only with transgender / transsexuals but anything sexual (i.e.: rape victims). After less than 4 months she told me she believed I was transsexual; then made me read about all the awful things that could happen, might happen and will happen. Nothing was mentioned about the good things. So I was confronted early on with the difficulties should I decide to become a woman. I chose to go ahead and yes many of those awful and terrible things have happened. A few of them I was prepared for and knew what to do, but others were surprises. Everybody should be made to read what I had to read and be informed.

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