Should You Transition? 3 Tips For Gender Questioners

We’re not the only ones who go through metamorphosis. Maria Sibylla Merian, 1705. Thanks to Alma for pointing me to Merian’s work. Source.

Whether to undergo gender transition is a profound and challenging decision. It’s a question each gender-variant person has to answer for themself. As someone whose life has been transformed for the better by transition, I wanted to share a few ideas that might be useful to those wondering where to go next.

First, a reframe. In most cases the question is not so much, “Should I transition?” but rather “How should I transition?” In the broadest sense, transition is a process of personal growth and change in which we adjust our lives, self-expressions, bodies and social roles to foster a healthier, happier and more harmonious existence. The list of possible transition steps is endless, and no two transitions are exactly alike. For some folks, transition in any form is just not feasible due to safety concerns or other circumstances. At the same time, more and more people are finding ways to trade out gender dysphoria for gender joy.

If you are profoundly unhappy with your gender status, chances are you would benefit from some form of transition–that is to say, some kind of readjustment, internal and external, to relieve pain and nurture contentment. What might that adjustment look like for you? How do you figure out where to start, and where to stop?

1. Forget the narrative. This is easier said than done, but seriously, as much as you can, disregard the dominant transsexual narrative. You know the one I mean–the one where you came out at age 3, where you take a specific dose of specific hormones, where you have specific surgeries in a specific order, where you look and fuck a specific way post-transition, etc. This is just as important whether you are a trans woman or man pursuing a conventional transsexual transition or a nonbinary or otherwise gender-variant person charting a different path. The narrative was not created by trans people; it does not serve trans people; and it will pretty much make you feel like shit regardless of who you are.

You are going to feel inadequate, illegitimate, not trans enough, not man or woman enough, etc. You are probably feeling this already, and it is going to happen over and over again. This is part of being trans in an intensely transphobic world. Recognize these thoughts and feelings for what they are: internalized transphobia. Don’t let them run your life.

2. Get playful. Gender questioning feels like a very serious business, and in many ways, it certainly is. These are life and death issues, after all. Yet when we labor under the weight of this great seriousness, we severely limit ourselves. It’s like trying to learn to swim with a bag of bricks on your back.

Instead, to whatever degree you’re able, take a playful approach to your gender journey. Somber, high-stakes, stressed-out struggling is no way to pursue happiness; it will only lead to more struggling. If we want to create conditions of ease, contentment, and harmony, we must begin to live that reality now.

What does gender playfulness look like? The specifics vary widely, but basically, you give yourself permission to explore, try things on and pursue what appeals to you in an open, low-stakes situation.

Say you’ve always wanted to wear panties or boxer briefs. You may agonize about what this means about you, what it indicates about your future surgeries and whether you’ll ever find love. That’s okay–given the cultural context, of course you feel that way.

You can also just buy the damn thing, put it on and see how it feels. You can do this without condemning yourself or attempting to predict the future. Just put the underwear on and sit there and notice how you feel. Then take it off. Then put it on. Then try one in a different color. Prance or strut around the room. Have fun with it.

Release your gender-variant inner child, who never got to run free and play properly. From a place of love and respect, let that kid run wild on the big open field of gender. Don’t build fences, chase them down or put a leash them. Let them play, trusting in their innate intelligence, like a wise parent who knows that the bumps and scrapes of youthful summers pose no serious danger. Then, see what happens.

3. Honor your responses. As gender diverse people, we have become experts in silencing, ignoring, repressing and mistreating ourselves. This has got to change if we are ever going to feel okay.

Learn to listen closely to yourself. Feel the subtle ripples of joy, shame, anxiety, and desire that move through you. Hear your body’s moans of pleasure and of misery; listen to the commentary of your chattering thoughts. Do this as you play with gender, as you go about your day, as people call you whatever pronoun, as you eat your lunch, do your job, etc. Notice when you feel scared, contracted, limited, and nauseous; notice when you feel relaxed, open, beautiful and whole.

All the information you need is already within you. Contained in the secret movements of your thoughts and emotions is everything you need to know to manifest your metamorphosis. The key is to start really listening to this information, and above all, to honor it. Let your heart and body be your guide. Follow the thread of joy with complete faithfulness.

Your own responses will tell you where to begin, where to move next, where to sit down and rest awhile, and where to call home. There is no other source of this wisdom. You must look within, and you must do so with a loving heart and an open mind.

Meditation is a wonderful tool for accessing the world of wisdom within you. Meditation has been a complete game-changer for my mental health and self-acceptance; it really helps me with internalized transphobia, dysphoria, and anxiety. If you don’t have a meditation practice, you might want to look into the contemplative wing of your tradition (if you’re religious), try secular mindfulness meditation or learn about other traditions.

Readers–what advice would you give to someone wondering whether and how to transition? For those who are questioning, where is your journey taking you today?



  1. PlainT

    Reblogged this on Queering the Nerd and commented:
    This is wonderful. Full of advice about not fretting about extremes, being kind to yourself, listening to your own reactions. Be kind to yourself; gender can be fun.

  2. Tea With Ess

    This is the approach I try to have, thanks to the safe environment my wife creates (she likes to help me play with the gender-stuff). Sometimes it goes really fast and sometimes it goes too fast and I take a break. But most importantly I try to have fun during the process. The reflection bit is nowadays a part of my everyday life anyway, so I don’t think too much about it.

  3. Clare Flourish


    I saw the gender psychiatrist with several “rational” arguments why I was trans and should transition. He demolished them all. I was left with what I felt.

    And when what I want to do with transition this year was too big to consider, what I want to do today was manageable.

  4. arhizome

    I started intentionally paying attention to my dreams and journaling about the images / feelings I remembered. As it turns out, my subconscious was already transitioning. In the dreams in which I present my felt sense of gender, I experience extraordinary feelings of ease and peace. This affirms to me that I’m on the right path.

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  6. UnknownJamie

    Reblogged this on Don't make me choose! and commented:
    I’m reblogging this too, fantastic three points and I’ve learned a lot. It is important to make the process personal, transition ought detail personal values, not societal ideals. There is perpetual balancing, so the less burdens we try to carry, the freer we are. Thank you for this post, it feels like a bedrock article and should be widely read.

  7. Nour S

    Reblogged this on The brighter side of the moon.. and commented:
    This is very wise indeed, sometimes I find myself doing exactly this, and sometimes I just drift away and get carried away by the pressure .. After all, there’s no right or wrong .. be true to yourself, embrace yourself, your emotions .. only you can set the pace ..
    My friend, thank you for a very wise and amazing post ..

  8. doubleinvert

    For me, this is probably one of the most important things to ask myself as I pursued and continue to pursue gender transition: ‘First, a reframe. In most cases the question is not so much, “Should I transition?” but rather “How should I transition?””

    — Connie

  9. Pingback: [Reblogging] Should You Transition: 3 Tips For Gender Questioners | doubleinvert
  10. Ronnie

    This is a great and very practical article. After 59 years of silencing, ignoring, repressing and mistreating myself, I realized that This has got to change if I am ever going to feel okay. Girl that is the truth. The point is we have to get rid of the No we tell ourselves. One needs to question themselves. I figured out that Gender Dysphoria is really my best friend. It is my True Self trying to tell the phoney I have tried to create to step to the side and take notes. The true self just needs to be allowed to break the eggshell that the phoney self builds as a defense for our ego. When we do that we begin to heal in small steps. I have miles to go…but the sense of how to do it…you have made simple and understandable. It is just that simple too.

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  13. Raine

    I’ve been struggling with how to approach transitioning in a healthy, constructive way and your points have truly shed light on the ambiguity and stress of it all. Thank you.

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  15. Shale

    Thand you so much! I have read a lot of stuff that either reaffirms a more binary and body-centred approach to transition or reaffirms the common “narrative” and I found it really hard to relate to that stuff! This made me feel so much happier and freer about questioning! I will definitely give this a shot. Thanks again!!

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