X-Treme Tshuva: Gender Transition as Spiritual Renovation

A Talk to Kolot Chayeinu on Rosh Hashana
by Joy Ladin

            When my friend Linden Grazier, who suggested I explore the parallels between making tshuva and gender transition, I was delighted. Gender transition is usually talked about as a medical process of changing one's body, or a social process of changing one's identity. But when transsexuals try to explain why we change our bodies and accept the often devastating consequences to our relationships to our families, friends, employers and communities, we tend to talk in spiritual terms. We aren't “making lifestyle choices”; we change our bodies and lives to make them reflect our souls. For us, changing names and pronouns and clothing choices isn't about changing our appearances: it is about revealing, for the first time, our true selves, our best selves, the selves we were literally dying to become. In short, as Linden suggested, gender transition is an extreme version of tshuva, a process of changing our lives to reflect who we truly are and to grow into the people God created us to be.

            For years, Yom Kippur was the best and worst day of the year for me: the best, because I could sob openly about a life that felt horribly wrong and wasted, and the worst, because I knew that no matter how hard I sobbed, I would continue to live that life. From the outside, of course, my life didn't look so bad. I was married, employed, had children, taught and wrote. But because I did those things as a man I knew I wasn't, I was only going through the motions. When my deeds were weighed on the balance of judgment, there was almost nothing there: a few dessicated grains on the side of good, acts of chesed I had done without feeling lovingkindness, moments when I had given to others without feeling generous. I was equally dissociated from my evil impulses, my selfishness, my meanness. When I hurt others, I barely felt it. When I lied, it barely registered – my whole life was a lie. For me, questions of good and evil were dwarfed by the mountain of bitterness, disappointment, and despair that grew every year I devoted to being a simulacrum of a man rather than a living, loving, human being.

            You don't have to be trans to experience these kinds of feelings. Many of us worry about the difference between the people we feel we should be and the people we are, about hurtful choices we make over and over, about potential we squander, about emptiness and disappointment we become accustomed to, about love, generosity, kindness we never get around to giving. Many of us realize that the selves we present to others, the identities we create in the world, don't fully reflect the people we know ourselves to be – and many of us choose, as I did for so long, to live with that sense of not-quite-trueness rather than upset our relationships and lives by “coming out” to others as our truest selves. As I describe in my memoir, Through the Door of Life, for transsexuals, these feelings tend to build year after year, into a consuming anguish: 

A man is standing in the shower.  It’s the weekend, it’s Saturday, it’s sunny, he’s in his thirties, his early forties, taking a long hot weekend shower, listening to his family – first one child, then another, then three together – screaming happily with their mother, the woman he has loved and been loved by since he was seventeen.  It’s the weekend, it’s Saturday, he is taking a long hot shower listening to the intimate noise of his happy family... 

            Some part of the man is glowing, far away, or far below, or somewhere within.  This glow is happiness, he tells himself.  There is another feeling too, a burning sensation, like magnesium blazing in water, a white-hot flame defying the cold, numb element – him – that threatens to smother it.  That’s love, he tells himself.  He is burning with love for his family, glowing with happiness at the sound of their happiness, and yet he is far away, or far below, or somewhere within, watching the blaze of his most intimate connections shimmer as though through fathoms of water.  These are among the strongest feelings he has ever had, and yet he cannot feel them. 

Because he is the kind of person who always talks to God, he says to God, “You see how much I love them.  You see that I’m happy.  Thank you, it’s enough for me, it’s more than I ever imagined.”  And then he adds, “I’m so tired God.”  And then, as the pain of the distance between himself and the life he is living overwhelms him, he prays a prayer he knows can never be forgiven:  “If it’s OK with you, and it would be OK for them, please let me die.”

Eventually the man gets out of the shower.  The happiness, the love, the pain – so intertwined he can’t imagine one without the others – sink to bearable levels.  He settles back into his sleeve of numbness:  skin, shirt, trousers.  When he opens the bathroom door, he smiles.  He knows this will happen over and over.  It is a sign – the stigmata, he might have thought, if he had grown up on the right-hand side of the Judeo-Christian hyphen – of a good life, the very best life he can permit himself to imagine.  And some day, he promises himself, this good life will finally be over, and he won’t have to endure his distance from it any longer.

There are reasons for his distance, his despair.  The sex of the body he was given is at odds with the gender of what therapists might call his psyche, and religious people might call his soul.  He calls it his “self,” and although it is faint, wispy, formless, without a life or a body to live it, although no one, not even he, has ever glimpsed it, it is the only part of him that has ever felt real.  His insistence on – or is it knowledge of? – the reality of the least lived aspect of his life has terrible consequences for the other aspects.  They hardly feel real – they hardly feel – at all.  He knows that this absence of feeling, this unreality, and the ache and vertigo and desire for death that accompany it, are called “gender dysphoria.”  He knows that gender dysphoria has always been with him; he knows it will never go away.

What he doesn’t know is that every day that he fails to live that unrealized self, his gender dysphoria will grow worse.  More painful.  More disorienting.  Harder to live with.  More costly to ignore. (21-22)


            Dan Savage's efforts to offer hope to young lesbian and gay people struggling with suicidal despair has made the phrase “It gets better” famous. But for that man standing in the shower, clinging to a life built on a self he – I – knew wasn't true, life wasn't going to get better; it was going to keep getting worse, until I hated it enough to end it. The realization that I couldn't keep living as someone I wasn't should have been the beginning of my “extreme tshuva,” my determination to turn, no matter what the cost, toward the life, the true life, that I had never known. But though despair can be a crucial step toward teshuva, suicidal despair isn't: for years I not only despaired of the life I was living, I despaired of life. That despair didn't prompt me to make teshuva; it froze me into place.

            Many of us think of tshuva in terms of sin, guilt, and punishment. Certainly, our High Holiday liturgy is rich in guilt-inspiring language. But the point of this language, and the difficult process of self-examination to which Elul is devoted, isn't guilt, or shame, or self-flagellation. I spent forty-plus Yom Kippurs feeling guilty and ashamed, enthusiastically pounding the body I hated without really making tshuva. No matter how passionately I wept, my sense of failure as a human being couldn't lead to tshuva, because it kept me focused on the person I didn't want to be rather than pointing me toward the person I needed to become. Teshuva requires not only unsparing analysis of what we have done and been. It requires us to imagine the truer, larger, more loving, more forgiving selves we can, and must, become. Our New Year liturgy not only imagines God reading the book of what our lives have been; it calls each of us to imagine what we will make of that book in the year ahead.

            After four-and-a-half decades of living as someone I wasn't, I had no sense of who my truer, larger self might be. To find out, I had to let go of the self and life I knew, and – do what? I knew all about the external process of gender transition, the hormones I would need to take and the new ways of dressing, talking, walking and so on that would enable me to present myself as a woman. But I didn't know the true self that gender transition was supposed to express.

            Jewish tradition says nothing about gender transition, but it has a lot to say about becoming ourselves. So it isn't surprising that, as I describe in Through the Door of Life, I found the wisdom I needed not in the how-to guides to gender transition but in Rabbi Hillel's famous questions in Pirkei Avot: “If I am not for myself, who will be? If I am for myself alone, what am I? And if not now, when?”

            Hillel's questions transformed what seemed to me metaphysical impossibilities into concrete choices.  “If I am not for myself, who will be?”  Hillel didn’t have to know anything about transsexuality to know that the answer to that is “no one.”  No one expected me, needed me, or even wanted me to become myself.  In fact, my family clearly needed me not to become myself.  My journey toward becoming a person could only begin with the radical act of being-for-myself suggested by Hillel’s question.  Being-for-myself seemed selfish, solipsistic, even psychotic, for I would have to be for a self that didn’t yet exist.  But Hillel showed me … that if I wasn’t for myself, my self would never be. 

Hillel’s first question leads inexorably to his second: ...“If I am for myself alone, what am I?”  Over the years, I allowed myself moments of being for myself, of letting myself surreptitiously, guiltily, relax the rigid discipline that ensured that I would always sit and walk and talk like a male, and feel, for a second, like the girl or woman I knew myself to be.  But those episodes were few and far between... They didn’t transform me into myself; they seemed to prove I had no self to become.  Hillel wouldn’t be surprised.  We become ourselves with and through other people.  My sense of myself as female was a private matter of being for myself.  But being a woman is much more than a sense of being female.  It is more than wearing certain clothes or sitting in certain postures, more even than having certain chromosomes and reproductive organs.  Women remain women even after double mastectomies and hysterectomies.  “Woman” designates a social status, the achievement of a mature female identity in the world.  When I was for myself alone, what was I?  A wish, a longing, a perversion, a disappointment, a half-remembered, shameful dream.  No matter how fiercely I insisted that I was female, if I wanted to become a woman, I had to remake myself in the eyes of others, to be for and with them as the self I felt driven to become.

But Hillel’s question is more than a call to come out of the closet.  It is also a demand that we take responsibility for the consequences to others of our becoming.  If I am not, cannot, be for myself alone, if I need others to become myself, then I cannot ignore the pain that results from my becoming.  However much I’ve suffered, my self and my life are no more important than the suffering selves and shattered lives of those whose destinies are tangled with mine.  People I love are in anguish as a consequence of my transition, and unless I acknowledge that that anguish is as real as the anguish that drove me to transition, I will be for myself alone – and if I am for myself alone, what am I?  The fact is that the best moments of the life I am making will always be intertwined with the worst moments of the lives of those I love.   It isn’t fair; it isn’t what I want or intend; but it is true.  For most of my life, I tried to be for others without being for myself – to be the man they needed me to be, to suppress and deny the woman I felt I was.  Once I began to transition, I wanted desperately to do the opposite, to insist that after all the years of self-denial I had given them, their feelings didn’t matter, to demand that they embrace and support the miraculous, cataclysmic process of my transition from death to life.  Hillel’s question forced me to recognize that to become a person, a real person and not someone acting like a woman, I had to be both for myself and for others, to be as true, as compassionate, as present to my family and friends as I was to myself.

Being for myself, being for others – it all sounds very static.  “Being,” after all, is the most minimal possible verb; it doesn’t specify any action beyond mere existence.  Hebrew doesn’t even bother to assign a word for it:  there’s no “is,” no “am.”  And that is why Hillel’s final question, “If not now, when?” is so important.  It reminds us that being demands becoming, that without constant, urgent, complete commitment, we cease to be.

For most of my life, it seemed that the answer to “If not now, when?” was “never.”  My ... certainty that I would never be for myself or anyone else, was so complete that I couldn’t even think of becoming as a process.  I imagined simply waking up into a magical now in which I suddenly was a girl or woman – and since I knew that could never happen, I tried to accept that I would never, in Hillel’s sense, be.  Once I made the difficult commitment to transition – once I answered “If not now, when?” by saying “now” – I expected instantly to become myself.  But transition didn’t magically transport me from life as an imitation man to life as a real woman.  I had to create that now – the now of becoming myself – not through one magic “Yes!” but through innumerable, sometimes agonizing decisions, choices, commitments.  And as I made those decisions, choices, and commitments and lived through their consequences, I found that I was slowly becoming the self I had waited my whole life to be – not a self alone, but a self responsive and responsible to those around me, a self who was for them as well as for myself.  That process continues, for every day I have to answer the questions that are the essence of becoming. 

Transsexuals’ lives may seem strange, even bizarre, but the questions we face in becoming ourselves are the questions life[, and teshuva,]pose to us all:  How can we become ourselves?  How can we put the selves we are becoming into meaningful, moral relationship to others?  And when we finally become ourselves, who will we be? (15-17)


            The extremity of my need for tshuva – the utter falseness of my male self, and my blank-slate openness to discovering my true self – made it relatively easy for me to embrace Hillel's questions, and the ceaseless process of becoming to which they lead us. Hillel's questions become harder to face when we are living more or less as ourselves already. Jewish tradition teaches us that being “more or less” is an unavoidable consequence of being human; our Sages envisioned life as akin to “Chutes and Ladders,” a journey in which we are always climbing higher and slipping lower, toward and away from God. That's why we have the Days of Awe – so that we can begin every New Year feeling forgiven for the ways in which we were less than we could have been, and freshly committed to becoming more – truer to ourselves and others, not yesterday or today, but now. 

            There's a famous poem by Rainer Maria Rilke that ends, “There is no place here that does not see you. You must change your life.” When we feel truly seen, we respond with tshuva: we know we must change our lives. The penitential prayers prompt us to feel seen by God, offering image after image of God remembering us, judging us, counting us like sheep, examining every our every deed and thought. But if tshuva only required us to feel seen by God, the Days of Awe would be devoted to private meditation conducted far from the distractions of friends, family, the sounds of allergies and infants, the irritations and enticements of community. Instead, we spend most of them together – because to realize that we must change our lives, we must feel seen by those around us, those with whom, through whom and for whom we become ourselves.

            I have always felt seen by God. Like many transkids, I talked to God all the time. God was the only one who wasn't fooled by the boy and man I pretended to be. That sense of being seen and known by God literally kept me alive. But the sense that God saw me wasn't enough to stimulate tshuva, because I felt invisible to those around me. There was no place where I wasn't seen by God, and no place where I was seen by my fellow human beings. That sense of invisibility warped my moral and ethical development. My life as a man was built on the moral premise that I owed it to those around me to completely conceal who I truly was. I was proud of living so wholly for others and so little for myself – and I was deeply ashamed of the cowardice, lies and evasions, this life for others required.

            Beyond this general pride and shame, I didn't have a clear moral compass. I couldn't, after all, be honest; I had to lie for the sake of others, and that made it difficult to recognize the other lies, the lies I told for convenience or advantage. Though I loudly joined in to Vidui, the communal confessions of sins, I wasn't really confessing to and with my community. I had no community, no one who had ever seen me, no one who could truly love or forgive or call out the best of me.

            I did have a sense of relationship to community when I lived as a man, but that relationship was defined in negative terms: I had a sense of rejection, exclusion, fear of how others would respond if they ever discovered – if I dared to live – my true self. No matter how much friends or family seemed to love me, I was sure they would despise the real, transsexual, gender-confounding me. This assumption constitutes what the State Department would call “a well-founded fear of persecution.” Every day, trans people are thrown out on the streets by their families, bullied, harassed, turned down for jobs they did before transition, refused housing – and most weeks, one or two trans women, often trans women of color, are killed. But I didn't know how others would treat me if I began living as myself, and however understandable my fears, by basing my life on them, I was basing my life on lashon harah, slander against humanity in general, and the people I knew in particular.

            Until I risked becoming myself, I couldn't stop, or even recognize, this slander, much less make teshuva. I've now had five years to test my fears of rejection and persecutiion against the reality of individual responses to my transition. The results, predictably, have been mixed. I've been rejected by some of those I was closest to; I've been stared at and stared away from, I've been the butt of transphobic remarks in print and in person (once, for two hours, on a bus), and I carry a very real fear of physical assault with me wherever I go.

            But I was wrong, deeply, utterly wrong, in assuming the worst of humanity. After a year of “involuntary research leave,” my Orthodox Jewish university allowed me to return to teaching – and a couple of years later, promoted me to full professor. My return was precipitated by students who went to the Dean repeatedly to protest my exclusion from campus. While Stern isn't anywhere near making the list of best schools for LGBT students, when one of my students heard that a transgender student would be arriving in the fall, she posted a call on her Facebook page for allies the student could turn to – and received many positive responses. My students not only showed me how wrong I was about humanity; they challenge me to live up to their example, and respond to differences I don't understand in ways that affirm that whatever we look like and however we live, we are made in the image of God.

            The extreme tshuva of gender transition has enabled me to become enough of a person that I can now engage in the less-extreme forms that are the life-long obligation and the blessing of every human being. I now have real relationships, relationships based on my true self rather than a male persona, and that means facing tough questions about how my life affects those whose lives are bound up with mine. As you can see in Through the Door of Life, the toughest questions come not from God, or Hillel, but from my children :

            “So now you’re happy,” my older daughter says as we sit in the driveway, questioning and accusing and hopeful that for me, all this pain has been worth it.  We’re side by side in the front seat of the car, watching a bird fly in and out of a nest built above a metal eagle that decorates the landlady’s garage door.  It’s quiet here, away from the constant three-way fight for my attention that will resume the minute we return to the apartment.  Life seems simpler, safer, seen through the windshield:  a garage, a nest and a bird who, for all her fluttering, isn’t going anywhere.

            “No,” I say... “I’m not happy.”

            “But isn’t that why you left us?  So you could be happy?”  There’s no edge to her voice now, none of the sarcasm that cuts us both so deeply.  She really believes that I left them to be happy:  that’s the story they tell themselves to explain the inexplicable tragedy of my transition.  It isn’t true, but I’ve been reluctant to challenge it, because I know that story restores some of the clarity, the certainty, that my transition destroyed, channeling the anger that threatens to overwhelm them, reducing complicated, painful questions about my motivations and choices to a single, simple sentence:  I left my children to be happy.  My happiness mattered more to me than their misery.... 

A[nd] as angry as the happiness she imagined made her, my daughter also found it comforting:  she wanted her tormented, tormenting father to be happy, because, for all the pain my fecklessness had caused her, she couldn’t help loving me.  And because she couldn’t help loving me, my happiness made her sad, because the life she thought made me happy didn’t seem to include her. 

I’d first glimpsed that tangle of love and sadness last summer.  The violence of her rage had abated, and I began acclimating her to the sight of me dressed as a woman by showing her pictures on my computer.  My son had glanced at them and grunted, “Not as bad as I thought.”  My daughter, though, stared in silence, tears welling in her wide brown eyes and spilling down her freckled cheeks. 

“Why are you crying?” I asked her.

“Because I’ve never seen that light on your face,” she murmured.  “Even when you look at us.” 

“Yes,” I answered.  “That’s one reason I want you to see me as myself – to share that light with you.”

But …. how could a ten-year-old understand that the happiness – and it was happiness – of living with my children as a shell of a man was harder to bear than the agony of living as a woman without them?  It was bad enough for my daughter to think that I would leave her to be happy; wouldn’t it be worse for her to realize that I had left her even though I knew that leaving meant misery?

It didn’t make sense, even to me.  But it was the truth.

“I didn’t transition to be happy,” I tell her.  “I knew that I couldn’t be happy without you.”

“Then why did you transition?” she asks quietly.

“I transitioned because when I was living as a man, I couldn’t be really alive.”

We’re clinging to one another now across the emergency brake that separates our seats. 

“And are you now?” she whispers, as though afraid to hear the answer.  “Are you really alive?”

She’s squeezing my hand so hard it hurts.

“Yes,” I tell her, releasing a breath I’ve held for two-and-a-half years.  “Now I’m really alive.”     


            I do tshuva around my transition with my children, not because I think transition was wrong, but because as Hillel taught me, I need to take responsibility for the relationships I created as a man, and the suffering my transition caused those whose lives were bound up with male identity. But this kind of tshuva is focused on the past; I want to end by focusing on tshuva I need to do as my true self.

            Of all the tears I shed when I was living as a man, tears that burned the most were those I shed over my inability to feel grateful for the life God had given me. How could I fail to feel grateful for a life that included so many blessings – family, shelter, sustenance, work I loved, the extraordinary beauty of the world? Feeling grateful for being alive, for the miracle and richness of life, no matter how hard it might seem – that is the tshuva that I do each and every day, because that is the ultimate goal of my transition. And when it came time to shape my stories of transition into a book – to literally write the book of my life – I realized that gratitude is where I had to start:

Every day I say a blessing in Hebrew over my medication:  “Blessed are You, O Lord our God, who has kept us, preserved us, and brought us to this time.”  That blessing is traditionally said at the beginnings of holidays, on the eating of new kinds of fruit, at any joyous occasion at which Jews want to heighten gratitude by becoming mindful of the singularity of the moment and the precariousness of the lives that have brought us to it.  It is not said on the taking of medication; it is specifically NOT to be said over daily events, for which there are different blessings; and it is never said over a disease.  

            The medications I take – progesterone tablets I swallow whole, and sweet circles of estrogen I dissolve under my tongue – are synthetic versions of the powerful hormones that naturally define and regulate many of the physiological characteristics of normal female bodies.  I don’t have a normal female body.  Born without the capacity to produce more than trace amounts of female hormones, for decades my body instead has produced testosterone, masculinizing my face, bones, muscle, hair, and skin. 

Though there are few aspects of my physical form unravaged by testosterone’s effects, thanks to my medication, those effects are diminishing.  For the first time in my life, when I look in the mirror, I see someone who has begun to resemble – me. 

            I never thought I would see myself in the mirror.  I never thought I would hold the means to become myself in my hands, that I would taste it dissolving under my tongue.  Every day that I take this medication brings me slowly – very slowly, for there is so much to change and my body is so reluctant, after all these years – closer to being the person I have always paradoxically wished to become and known myself to be.

At a stage in life – middle age – when many face the facts of mortality, I am experiencing rebirth – or at least, re-adolescence.  This perhaps is only fair, since I spent so much of my life as a ghost, haunting a body that didn’t feel like mine.  Rather than embodying my identity, my body erased me, proved that I didn’t, couldn’t, exist.  Now, every day, my body and I move closer toward belonging to each other.

            This transformation is more than physical.  As my body learns to metabolize and distribute fat according to female rather than male patterns, I am learning to live, and to be alive.  The sophistications accumulated over four-and-a-half decades, the blasé attitudes, the taken-for-granted mechanics of daily life, have fallen away.  Consumed by the ravenous insecurities of adolescence, I am shy, awkward, always verging on the inappropriate, a maelstrom of feeling and need, fear and excitement.  The first times such identity-forming growth spurts happened, I was an infant, then an adolescent, too young and too caught up in the painful processes of becoming to register them as miracles.  I have watched these processes as a parent, but I never expected – I had given up hope, and was perhaps too foolish to fear – that one day I would be watching myself learn to walk and talk again, to say hello to grown-ups, to order in restaurants, to shop for clothes, to make friends.  All this  has become new again.  Going to work, riding a subway, making a business call – each experience has become an adventure, uncomfortable, unpredictable, brimming with emotion and discovery.

But this newness is only the beginning of the blessings my illness has brought me.  While I hid in the shell of my pre-treatment body – a body which, though monstrous to me, was accepted as normal by those around me – I felt I stood outside the human species, a species heartbreakingly beautiful and dauntingly strange, creatures who belonged to and with each other.  I loved humanity from afar, passionately but impotently, giving little of myself, because I had no real self to give.  And honestly, what could I know of love, when my every act and word presumed that I would be instantly rejected by anyone who saw through the shell of my maleness to the unrealized creature squirming within?  My self was a tissue of terrors and lies, an automated, reflexive cowardice perfected as a child.  If love is based on authenticity, I was incapable of it, for I had never lived a day, a moment, as my true self.

            And so it has come as a profound shock to discover, at the time of my greatest vulnerability, that I am surrounded by love.  As I have become known to those around me – people from whom I had always hidden – I have been met again and again with compassion, acceptance, tenderness, generosity of spirit that seems to have no limits.  A few have embodied my worst nightmares of rejection.  But my overwhelming experience has been to find myself in relationship to the finest, most loving human beings I can imagine.  And because I am once again at that awkward age, when every discovery breeds a new insecurity, a new challenge, a new possibility of failure, I feel dwarfed among these grown-up souls for whom loving and giving are as inevitable as breathing.  Is it too late for me to learn to follow their examples?  It is far too late to be asking such a question, but it is still too soon to answer.  All I know is I am filled with love, too much love, love straining the cramped circumference within which I have always lived.  Perhaps this problem is the ultimate blessing.  What, I wonder, will I ever do with all this love?

Every day brings me closer to becoming the person who not only can but must answer.  And so every day, when I take the medication that is making this possible, I say the blessing that registers the wonder and privilege of being, the awe and responsibility of becoming:  Baruch atah Adoshem, Elokeinu melech ha-olam, shehechiyanu, v’kiyemanu, v’higeyanu, la-zman ha-zeh.


            Shana tova, and may we all be inscribed for a year of healing, a year of growing, a year of becoming, a year for which and during which we are truly grateful.


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