Of all my parental accomplishments, I am particularly proud that I have managed to delude at least one of my children into thinking that I am both omniscient and clairvoyant, and that beneath my rapidly thinning hair there lurks a never-sleeping eye always spying from the back of my head. My youngest son believes that I see his every move and know his deepest secrets. On countless occasions, I have anticipated his needs as if by magic. For example, without looking up from my laptop, I will nonchalantly hand him the book he is looking for. Feigning a yawn, I might say, “This what’cher lookin’ for?” I delight in giving one-word answers to questions that are just about to leave his lips, leaving him sputtering, wondering how I knew what he was about to ask. From across the house I have heard an almost inaudible clinking, compelling me into the kitchen just in time to find him pulling his still small hand out of a tub of off-limits jellybeans. I stand silently behind him, my jaw set, one eyebrow raised, forehead furrowed. He turns around, his paw loaded with a chaotic candy rainbow: busted again.

I hear him getting dressed after a shower, and I yell up the stairs, “Put on a clean shirt!” I know he has yanked on the same beloved but filthy skull and crossbones T-shirt he has worn for the last two days. I creep up the stairs as he yells, “Dad!!!! I did!!” I catch him in the hall and tell him to show me what’s under his hoodie. He growls and shuffles. “Okay buddy, let’s see then…” I wait. He grumbles. I know the grimy black-and-white Davy Jones lurks just underneath his sweatshirt. “Wanna show me, bud?” I ask. He delights me by becoming simultaneously indignant and sheepish. I respond by channeling Clint Eastwood, curl my lip and point at his chest whispering the command: “Clean T-shirt, Mister…now.” He stomps back into his room, crashes around, opens his dresser, and then stomps back out of his room. I head back down the stairs. In my mind’s eye I see that he is about to throw the dirty shirt on the floor. I feel like Big Brother. I yell up to him, “Sir, put it in the hamper please.” He keens, “DDDAAAAAddddd! Whaddaya think I’m doing!” He rails against me, hollering accusingly as he clambers down the stairs after me, “Why do you always blame me?” I look at him with confidence, lean toward him, and softly say with an Indiana Jones grin, “Dude, I am so on to you.” At that moment his indignation fades, and glimmer of admiration flickers in his eyes. On his face is an unspoken question: “Wow Dad, how’d you do that?” And, with love, a dash of fear, and a dollop of fascination, I can see that he thinks I’m an evil genius. Which, for the record, I am not.

What I am is a transgender person who as a child survived the 1960s in America, who came of age in the late 1970s in Los Angeles, and who managed to fit into the world of politically correct, come-to-consensus-OR-ELSE lesbian feminism in the San Francisco Bay Area in the 1980s. All my life I have been profoundly aware of how I do or do not fit into my social surroundings. Mostly I’ve lived outside the norms of femininity. I have been a tomboy, a firefighter, a butch dyke rock drummer, a deckhand, a neo-Hasidic androgyne, a Jewish lesbian spiritual leader, and finally, a married-with-children, transman rabbi-maggid serving a small congregation. Hardly the trajectory presented to me as a girl-child. I realized early on that if I was going to live to tell the tale, I could either totally tune in to the subtle cues of my cohort and conform, or I would have to utterly ignore all social conventions and bushwhack my way through the binary gender jungle. Mostly, I’ve done the latter. Regardless, I had to know who I was dealing with at all times, and take a chance on finding a way to fit in, or be so outrageous that fitting in simply ceased to be an option.

There is a teaching in the Talmud, “Dah lifney mi atah omed,” which is usually translated as “Know before whom you stand,” or in contemporary parlance, “Yo dude, don’t look now, but God is watchin’!” Our rabbis insist that each of us is being seen, understood, known, and considered in every moment, every act, and every feeling. Dah lifney mi atah omed is a reminder that even in our most private moments we are standing before God. This is the very feeling I have tried to instill in my son (and it seems I have been somewhat successful). I suspect that at this stage he feels spied on, interfered with, and controlled by my intrusions into his private life. In time I trust that he will understand that my nagging and rule-setting were an expression of just how much I loved him and wanted him to be safe and well cared for. However, I know that one day he will hit a difficult crossroads. Soon enough he will realize that his seemingly all-knowing parent was simply a very imperfect placeholder for God. And that realization will signal that his spiritual journey has begun in earnest, when—like Abraham—he leaves his father’s house. Oh yeah, that is when the real fun begins.

I never really had a “father’s house.” As a child I was unaware of any adults who had the foggiest clue who, or what, I was. For better or worse, my children are well-known to their parents, and we see them in all their complexity, with all their paradoxes. Growing up in the San Francisco Bay Area in the twenty-first century with queer parents affords our children a rather wide berth for their expression and identity. Gender? Schmender! As parents, our primary guidelines for them are that they be true to themselves, do more good than harm, and brush their teeth at least twice a day. I, on the other hand, was born in 1959, when gender unequivocally predetermined who and what I was supposed to be in the same way that a paint-by-numbers canvas dictates the movement of its painter’s brush. From early on I knew that I simply could not follow the rules of girlhood. I wouldn’t wear “gender appropriate” clothes, and I eschewed dolls, the color pink, and playing with little plastic tea sets. I was either the only girl in a pack of boys or I was alone. I generally just coped with the sad fact that there didn’t seem to be a soul like me for miles around. Thus, my spiritual journey began young.

Humans, as a rule, seek familiar others. We expect our children to look up to adult role models. And, like all kids, I observed and sought an adult version of myself, a fully formed example of who I might become. Sadly, the cupboard was bare. Women were made up and sprayed up and had huge pointy breasts swathed in bright floral prints. I could not see myself ever dressing that part. It actually scared me to think of it. Men, on the other hand, were cropped and boxy, tight and buttoned down. While slightly more appealing, that option didn’t feel like my destiny, either. Women seemed too colorful and sexy; men seemed too dour and dull. I was some strange hybrid: part serious and stalwart, part merry and gay. I was part boy, part girl, and everyone else seemed to be ALL boy or ALL girl.

By the time I was five years old I had developed a style and persona that literally stopped people on the street who, with no shame whatsoever, would ask, “Are you a boy or a girl?” I could barely answer them because I knew that there was a right answer (girl) and a true answer (no). This was a rough revelation in itself: to, recognize, at age five, that the right answer might also be false, and the true answer might also be wrong, set me on a lifelong path of confusion.

The more I looked around me, the less I felt there was a place for me. Instinctively, I developed my own version of Dah lifney mi atah omed. Rather than “Know before whom you stand,” my meditation was more like: “Know who stands in front of you (and do your best to be just like them).” And with that somewhat warped notion guiding the way, I launched my quest to find out who I was to be.

I suppose all of us develop methods of coping with our existential disappointments. The blonde, straight-haired kid who wishes to have brown curls; the goy who secretly covets dreidels, latkes, Yiddish, a god who laughs, and eight days of Chanukah; the girl who would rather be a boy. I was all of the above and was in deep need of a powerful rite that would help me transcend what seemed at the time a rather mean-spirited practical cosmic joke. That rite was a mind game I called “Who Would I Rather Be?” I played my game in line at the bank or the supermarket, at a movie theater or concert, riding the bus, sitting on the beach, anywhere and everywhere. It became my ritual, my supplication, my constancy, my meditation, my prayer.

Here’s how you play: 1) Look closely at all the people in your immediate surroundings. 2) Note age, stature, body type, style, ethnicity, identifying markings, and personal habits. 3) After perusing the variety of nearby humans, you have two minutes to pick the one you’d rather be.

It’s like a choice you would face if Let’s Make a Deal were hosted by God: would you cash out your life and identity for the good-looking, thirty-something stud muffin with ringlets standing next to Carol Merrill on the showroom floor? (For me, the more he looked like Mandy Patinkin in Yentl, the more likely my answer would be a resounding “YES!”) The goal of the game was identity suicide.

I played “Who Would I Rather Be?” for decades. I was so uncomfortable in my own skin that nearly everyone I saw seemed an improvement over being me. I was seeking definition, recognition, and simplicity. Like most of us, I had totally bought into the two-box gender system. There were men, there were women, and you needed to be one or the other. Deep down, I knew that I was a little of each, but if I had to choose, I was more drawn to masculinity than to my native femininity. Originally, I focused on physical appearance and discovered that I was prone to covet nice packaging. My longing was initially based on the paradigm of binaries. One could be male or female, handsome or ugly, smart or stupid, debased or respectable. This was supported by our culture, where we tend to cluster those qualities into a mythical perfect person. Thus, when I played “Who Would I Rather Be?” I assumed that a handsome fella would be smart and reputable too. Handsome outside equated handsome inside, so for a long time, the handsomest man, or occasionally a handsome woman, would be my choice when I played “Who Would I Rather Be?”

But then when I was about twenty-four the game crashed. I was standing outside a club in San Francisco casing the nearby crowd. While everyone around me was cruising for someone to be with, I was cruising for someone to be. There were loads of hot, hip people. I caught sight of a young man who was stunning to look at, exceedingly cool, understated but brilliantly coiffed, and sharply dressed. Ordinarily, he would have been a slam-dunk candidate for my imaginary morph. Then, just as I was about to mentally cash out my frumpiness for his elegance, something shattered my reverie. My vision of him got very focused, and all of a sudden he looked “off.” I found myself looking past his beauty, his fit, smooth body and silky masculinity, to a place an inch or two below skin level. There was, in his spirit zone, an energy that did not seem smooth and beautiful, but rough and bitter. The tip-off was at surface level: I saw a brief facial spasm, a split-second sneer that warped his otherwise heavenly mouth and sent a shock through me. I looked closer at his eyes: slightly cold. Then I noticed his jaw kept flexing and relaxing, popping a cheek muscle up and down like a jack-in-the-box. His hands were busy wringing, dancing in and out of his pockets, fussing with a button, raking through his hair. Nice hands, but none too clean, and his nails were bitten-down pink.

On a macro level, this man was beautiful and put together, but deeper, he was unsettled. After studying my fellow humans for two decades, I had finally developed an eye that really could see who stood before me. Twenty years of research, practice, and prayer paid off. The scales fell from my eyes, finally debunking the myth of human perfection. That night, surrounded by sinewy, well-clad hipsters, I broke the chain and chose to be imperfect, gender-confused, and flaxen-haired. I chose me.

Alas, old habits die hard. I continued to play, to scan the faces, the hairstyles, the clothes, the bodies. Observing people had become a habit, but my eye had been changed. Other people didn’t seem so perfect anymore. I began to notice that lots and lots of handsome people had unpleasant habits, or were just as anxious and insecure as I was. It was getting harder and harder to find a slam-dunk persona I would have preferred being. The closer I looked, the more I saw, and the more I saw, the less I coveted.

My faith in physical beauty and archetypal masculinity took a downturn at almost the same moment that the binary gender paradigm took a major hit. From the 1980s through the early 1990s an amazing cultural shift took place. The firm definitions of male and female were beginning to erode nicely. Annie Lennox donned a man’s suit and wore a mustache at the 1984 Grammy Awards. Boy George redefined manhood with mascara, lip liner, and a sassy hair band. In cinema, The Crying Game put forth a likeable, sympathetic, and brave (not to mention gorgeous) transvestite. A nascent queer aesthetic was emerging in the mainstream, of all unlikely places. A tiny group of gender-fluid people became visible, and they weren’t being laughed at. Their albums were being bought, their music danced to, their styles copied, their movies watched, and, by God, they were hot!

Amazingly, I found myself thinking that my own flaws weren’t so bad after all. More and more when I found myself playing “Who Would I Rather Be?” I passed up door number one and door number two because now there was a door number three.

Knowing who we are in relationship to the world and/or God and having a clear understanding of what is around us are flip sides of the same coin. Judaism is a profoundly relational path, and being transgender is as well. Dah lifney mi atem omdim, knowing both before whom we stand and who stands before us, sums up a big part of our transgender journey. To make sense of this world, transgender folks have to be awake and alert; we have to study and observe; we have to reconcile how things appear and how they really are. To make sense of ourselves we have to grapple with and integrate all the contradictions and paradoxes that we were blessed with from birth. I tried for so many years to see those in front of me as only utterly perfect or utterly flawed. That black-and-white vision diminished their wholeness as well as my own. When, finally, I was able to perceive the glorious grays, a depth of knowing began to supplant my discomfort and yearning. God’s complexity displaced my human desire to bifurcate. And thus, yea verily, did my complexity become evidence of my own holiness. No longer preoccupied with who stood in front of me, I began to know, rather, before whom I stood.

One day I’ll tell my kid that my “psychic powers” are simply the byproduct of studying the microscopic facial twinges, vocal tics, and naughty tendencies of my fellow humans since I was half his age. I will explain to him that it’s a habit that developed into a prayer of sorts. I’ll let him know that my superpowers are a vestige of my youth as a tranny-in-training, and I’ll share a little Talmud as I bless him: Dah lifney mi atah omed.

© 2010 by Jhos Singer. Adapted from the essay in Balancing on the Mechitza: Transgender in Jewish Community, edited by Noach Dzmura, published by North Atlantic Books.