Some Gender Transition Wisdom


My transition from living as a “special sort of man” to now living as a “special sort of woman” occurred gradually and gently over the course of about seven years. Here are some of the things I learned which served to make my transition smoother than it might otherwise have been. I hope you find these helpful as well! (Switch pronouns & examples to suit!)

Gender transition is really not something you should do alone if you can help it; include other people in your life transformation: I have been blessed to have a dear cisgender woman who has been my best friend and has been as a sister, a mother and mentor to me throughout this whole process – she saved my marriage and likely prevented my suicide…

…And something else really important: I am convinced that humans are spiritual as well as animal beings, and for me it was crucial to include my Creator in my transition. Indeed, I feel it was this Person’s gentle “hand” that moved me through the process, of becoming the woman I am today, and who I will become tomorrow. If you are a person of faith, please know that you are loved by your Creator as your true self, whatever anyone else might say. You are no mistake, your true gender is a gift AND: You Are Loved!

So, in no particular order…

  • OWN your gender with a quiet, steady conviction. If, for example, someone won’t accept you as a woman, don’t let their view of you dampen your feminine expression (subtly supporting their wrong view).
  • Be nicer to others than you need to be (you become a ‘pleasantly peculiar’ person who is trans instead of a “tranny freak”).
  • Desensitization is a good thing for you AND others. Getting used to your own changes helps you build self-confidence. When others get used to the idea that you’re changing, then your next change will just be ho-hum to them.
  • Being trans is NOT the worst thing that can happen to you. Being trans is not the catastrophe your friends & family might assume it to be.
  • Consider the benefits of transitioning gradually: it’s hard to make a big mistake; it can be done on a shoestring budget; you can stay under people’s “freak radar;” you can put more thought into your transformation; others have more time to adapt to your changes (and so do you).
  • Remember that you are not deceiving anyone – you’re 100% yourself under the circumstances. It’s okay to evolve in your self-understanding, self-expression, and self-description. It’s called growing and even haters do it (well, sometimes).
  • Concentrate on your inner person at least as much as your outer expression. Inner beauty has a way of coming out, even when we don’t plan on it (so does inner ugliness!) Being a beautiful person on the inside is something that transcends our gender and our gender expression. Being a beautiful soul endears one to people of good-will (even if they don’t “get” us), while such beauty puts haters to shame.
  • Self-confidence is AT LEAST half of being accepted as the gender you are. Such is developed by getting out and being yourself until you become (relatively) comfortable in your skin. Know that being “at ease” with yourself helps others to be at ease with you. You don’t have to be 100% transitioned (nor even near it), nor 100% satisfied with your body or progress in order to have a relative degree of comfort with yourself.
  • Your vocabulary can help you transition. Think of the subtle differences here: “recognized as female” vs. “passing;” “recognized as transgender” vs. “getting read;” “privacy” vs. “stealth.” The former frame things positively and assume we are legitimate; the later live under a cloud that implies we aren’t real people.
  • Focus on the things you cannot buy – they will be more valuable to your assimilation than you may imagine. You can buy breasts, but you cannot buy a feminine demeanor, nor the ability to “girl talk,” nor feminine-street-smarts, nor a feminine voice (well almost never). Many of these things require observation, patience, practice, a “letting-go” of yourself.
  • Be willing to look and sound foolish – there are times when you will, and you won’t make progress unless you’re willing to make mistakes in public – just try to keep your mistakes small!
  • Observe cisgender people – people watch – it’s great fun!
  • Just do it…get out and be yourself, even though your expression will be imperfect, even though you are probably still trying to figure-out what to do and how to do it.
  • As you progress and all this becomes easier, start thinking about developing your style.
  • Yes, it gets easier with time and effort! Truly!
  • Transition is synergistic – all the positive things you do work together to make your self-expression, your presentation more and more authentically you. Things that seem impossible now, may become possible as you move forward in other areas.
  • Embrace the kindness of strangers. People can see when you are sincerely trying to grow and many of them will be delighted to help you along. Show your appreciation.
  • Lean-into your difficulties; as you do this you will develop a strength you never thought you had in you. And remember, your circumstances change like the weather – things won’t always be difficult.
  • Look for things to be thankful for; look for ways to be kind & compassionate. These will grow and beautify your inner person, and it will waft from your being like a lovely fragrance.
  • Once your gender presentation “tips the balance,” society will help push you the rest of the way over.
  • “Get over” what people might think about what you’re doing, how and why: because…
  • Most people don’t really care what you are doing. And no, not everyone is watching you all the time; AND besides, what they’re thinking about you really isn’t your business anyway. All this sounds harsh, but it’s true, and when you accept these, your life and transition will move ahead more smoothly.
  • Consider allowing people to gender you as they wish while you are transitioning; this has the advantage of allowing you to “fly under their radar” AND when people feel free to simply interact with you (and they are more likely to if you’re not verbally asserting your gender identity), you will get a more accurate idea of how well their gender perception of you matches your gender expression of your gender identity. It my seem to grate on you at first, but as you change, you will see people change their assessment, and the encouragement will be valuable; AND your transition is more likely to be seen as human growth rather than something disruptive.
  • Do what you can to make it easy for people to perceive you as the gender you are, then whether they know you are trans or not, they will tend to treat you as if you had been birth assigned this gender. This may seem obvious, but there are crazy things we do that can make it unnecessarily hard for people to see us as we wish to be seen.
  • Free Yourself! Many of us have known our gender for our whole life, but had to suppress what we knew, not express ourselves the way we wanted. You are free now, and giving yourself permission to *be* will move you forward in amazing ways!
  • Transition IS consuming for a while, years probably – you WILL eventually settle into yourself and you will “graduate.” (BTW, “graduating” doesn’t mean you have every change made that you may want or be planning. You can be fully a woman without (for example) having GRS (Gender Reassignment Surgery) – but once you’ve graduated, GRS is just “women’s surgery.”).
  • Consider that a tactical step-backwards could be what you need to make a strategic move forward.
  • If circumstances force you to scale-back, find another way, even if it’s small, hidden and known only to you – you’re still moving forward and it will help you stay positive.
  • Be gentle with yourself – as much as needed.
  • Visualize your successful transition – as much as needed.
  • AVOID NEGATIVE SELF-TALK!!!!!!!!!!!! (No one has the right to condemn you, not even you!)
  • Don’t act like a victim; don’t be angry with the world – it’s unproductive, dangerous and no one will want to be around you.  Yes we are often victims; yes our anger is often justified, BUT life isn’t fair and these two things will destroy your transition and life.
  • When someone gives you a compliment, accept it graciously and let it be like a soothing balm, and remember it, and replay it in your mind as much as necessary! (I write these down, and I keep a folder of them, and I bathe myself in them whenever I feel the need.)
  • Surround yourself with positive, supportive people. Be that kind of person to others.
  • Realize that everyone in your life will need to transition as you transition. The closer they are to you, the more radical and difficult their transition will have to be. Cut them the slack you would like them to cut you (whether they do this for you or not).
  • With relationships there are NO GUARANTEED OUTCOMES. NONE. Accept this with as much grace as you can.
  • Allow for grief. Transition is a bit like death and resurrection; there are parts of you that others may never see again, that you may never experience again. To many, it will seem as though you have died: allow them their grief (in all its stages). Don’t be surprised nor ashamed if you grieve over yourself also – who you were was not such a bad person, and in a sense “he” didn’t deserve to die: he may have been a good husband, father and friend; he sustained you until you could begin your new life, and he was a gentleman to step aide to now let you blossom & live: he was far from perfect, but please give him his due.
  • Communicate with your Significant Other. This can be as hard as hell, and hurt like hell, but hiding and sneaking about in your transition will “poison the well” like few other things.
  • Know your medications! Do your homework on your medical condition(s). Your doctor should not dictate the medical aspects of your transition. If your doctor does not agree with your goals, find another doctor and work on your transition in partnership with them. It’s your body and your life!
  • Don’t let anyone tell you that you aren’t what you know yourself to be. There are a LOT of ways of describing ourselves and (sadly) some folks like to use descriptors as boundaries-to-police rather than ways to help understand each other.
  • If you’re trans, you’re trans – you don’t need to “check all of the boxes” to be “trans enough.” YOU DECIDE if you’re transgender.
  • Do your transition YOUR WAY. Accept good advice, but it’s your transition, your skin in the game.
  • Don’t let anyone insist that you’re doing it wrong because you’re not following the “ACME Guide to Real Transition.”
  • You will probably be told that you are being selfish for transitioning. Put this into perspective: gender identity and its expression are a core part of being human – everyone expresses their gender and what’s legitimate for them is legitimate for you too. Someone assigned your gender when you were born, and they never asked you; well, their assumption was wrong and you need to be yourself. Self-sacrifice is a healthy, noble human virtue. Self-negation is a self-destructive, ignoble tragedy: even haters “get” this eventually. Make sure you are being yourself, and you will become a better human being for everyone else to be around.
  • Most parents want their children to be happy; a great many of our parents are scared-to-death about our transitions because they are afraid we are ruining our lives. Make sure that your parents see you happy! Help them understand that this is the right thing for you to do. Help them realize that their child is alive and happy, even if their son has now blossomed into a daughter.
  • Accept that some people may never accept you as you are; but that is not your fault, it is theirs.
  • Be kind! Be kind! And when in doubt, do the kind thing! (Being kind to others is also a way to be kind to yourself – the universe just works that way!)
  • Don’t be afraid to start-over. Transition itself is one of the most profound (and difficult & risky) “reinventions” of ourselves that a human can do. If, for example, you find yourself going down the binary path that includes surgery and whatnot, AND you feel that you’re really more genderqueer. DO NOT BE AFRAID to move to where you feel most yourself. It’s your life and this is serious business. Moving to your true self should never be seen as a backward-step – it’s always progress.
  • “Becoming” is a twisty-turny-path – but it’s like this for everyone, and that’s okay.
  • Don’t take everything too seriously (especially yourself)!  Laugh, giggle: yes, even at yourself and your circumstances. Honestly, there are aspects of all this that are insanely funny! (For example, I keep a list of my “Sir-Realities” – little humorous interactions I have with cis folk.)
  • Consider this: you’ve changed your sex – you can do anything else you set your mind to!
  • Don’t transition to be a man or a woman or something else: transition to be yourself – if when you find that after you’ve become that you’re one of these, then welcome home – you did the right thing!
  • Work on your “other stuff” – gender transition will NOT fix problems you already have and may make them worse. If possible, GET INTO THERAPY – it will be one of the best things you have ever done for yourself, I promise!
  • Know that in transitioning you WILL trade one set of problems (guy-problems) for a new set (gal-problems), you will also add many new ones (trans-problems). Most of us find the trade worth the trouble, BUT you’ve been warned.
  • Transition is: a “line-in-the-sand” –  I will not be this person any longer.
  • Transition is: a “passage we travel through” – I will become the person I know myself to be.
  • Transition is: “the rest of my life” – I live, mature and die as my authentic self.
  • Suicide as a VERY REAL RISK for us. Make yourself accountable to the people you love. Remember, the chain of events leading to suicide is slender and delicate – it can be easily broken – BREAK ITYOU are valued and will be missed by those in your life and in our community, even if you don’t think so! These saved my life!

    For immediate help call: TransLifeline USA: (877) 565-8860 Canada: (877) 330-6366
  • Always remember, we are ALL human beings FIRST. Everything else, second, third, fourth…

Here is the article that inspired me to commit these insights to writing.

Also, Passing Glances is one of the very best (and most fun) primers I have ever read on the subject of male-to-female transition. I strongly recommend it for anyone new to transition or those who are mentoring others.

Integration: As you move out of the most intense stages of transition, consider thinking about integrating who you were with you have become. Earlier generations of trans folk were forced into exile: obliged to abandon their loved-ones, their careers, their history, their lives, in order to become themselves; they had to run from one closet into a new closet. Blessedly, that is not required of us, by people who would help us, by the increased safety we enjoy and by our growing acceptance in society. Increasingly we are allowed to keep our relationships and histories, and integration means that we can choose to be our whole selves if we wish and without shame…

We experience life in a way most human beings do not, and we become gifted by what seemed to be a curse, if we allow ourselves to receive and embrace our lives in their entirety, and we are increasingly allowed to share this gift with others in and out of our transgender community.

…For me, who I was didn’t die, but blossomed into who I am now, and who I will be tomorrow; my task of integration is to allow Brett to emerge from his self-imposed coma, and allow him to be part of this existence also. We will be she, the blended person we always were, but this time Brettany will be the facet of this jewel that faces the world, and Brett, though turned-away from the public eye, will nevertheless strengthen his beloved sister, cheering her on and supporting her in her most difficult times to come. In this sense, I am more blessed to be trans than I am if I were cis.

Blessings & Joy!!

2 thoughts on “Some Gender Transition Wisdom

  1. I am wrestling with where i am on the continuum and reading this gave me so much insight. What a blessing to come across your words this morning. Thank you, my darling fellow traveller!


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