I was standing with the ark at my back, facing the congregation. Rabbi Annie, my davening partner and best friend, was standing on my right holding one of the Torahs. Members of the board flanked us on either side, each wearing their Yom Kippur best and holding a Torah in a resplendent white cover. The full membership of the congregation was looking back at us. My parents looked on from a row near the center. As the cello’s last notes rang out, I inhaled slowly, and exhaled the words and melody of Kol Nidre.This year, 2019, was different for me. The four years I had done this previously, I was wearing a suit and tie under my white robe, but this year I wore a blouse, women’s slacks, and flats with a buckle on them. No tie. My eyeliner and lipstick were best-friend/rabbi approved, even if they did go against traditional Jewish law. What others saw was that the cantorial soloist had gone from dressing in men’s clothing to dressing in women’s clothing. What I felt was that I had finally shown up.Growing up in suburban Houston, my family belonged to a massive Reform congregation where I had my bris, consecration, bar mitzvah, confirmation, and religious school graduation. I learned how to be a song leader and rose to the rank of co-president of our temple’s North American Federation of Temple Youth (NFTY) chapter, but that certainly doesn’t mean I ever felt like one of the cool kids. Entering ninth grade in 2006, my daily application of eyeliner accompanied by a rainbow of plastic bead bracelets up my arm won me the label “emo” and assured that my sexuality was called into question by everyone I knew—including myself.In high school in the late 2000s, I didn’t know about anywhere near as many label choices for queer identities as I do today. I never saw myself as a “gay man,” because neither “gay” nor “man” ever felt like they really fit. As one friend put it, “you’re gay, you just happen to like girls!” I was attracted to both men and women, which meant I had to choose between identifying as either bisexual or “confused.” For a while I identified as bisexual, but when that came with constantly having to gauge just how bisexual one was (70/30 one day versus 50/50 the next), the label stopped feeling right. “Confused” had a funny connotation, too, as if I existed in a state of tangled up mystery that I was constantly trying to solve. I came up with my own label: “confuser.” I explained to people that, “if I identified as ‘confused’ it would imply that I care, which I don’t. If I identify as ‘confuser,’ it implies that you care, which you clearly do.” The skills I was acquiring as a temple song leader helped me land my first job as a cantorial soloist in 11th grade at Temple Sinai, a small Reform synagogue in West Houston. Rabbi Annie had just arrived at the congregation, and a youth-group friend suggested I audition for the job. I started on a rotating cast of cantorial soloists, and eventually began freelancing at other small synagogues across the area.After graduating high school in 2010, I became a choral music education major at the University of Houston. Most of my fellow music majors, regardless of their sexuality, developed a strong interest in drag culture through the lens that RuPaul’s Drag Race was giving the world. Some of my friends became quite skilled with drag makeup and encouraged me to experiment, but I wasn’t interested in dramatically heightened femininity for weekend shows. I was, however, interested in learning how to present more femininity every day.My first job out of college was as one of the three full-time choir directors at a large public high school outside of Houston. I bought button-down shirts and polos and dressed the part of “Mr. Levine.” High school students were now responding to me with “Yes, sir,” even though people said I still looked 15. I was never comfortable with students calling me “sir,” and I always knew it wasn’t just about our slim age difference. Before I had words to describe why, I knew that being called “sir” wasn’t something I was interested in getting used to, even though well-meaning mentors told me I would. “Sir” just did not equal “me.” I wanted to find a way to avoid it altogether. I was starting to sense something wasn’t lining up by how frequently mentors and friends encouraged me to grow a beard to appear older and more authoritative and by just how revolted I was by the mere notion.That same year, I became the High Holy Days cantorial soloist and choir director at Temple Sinai. One day, Rabbi Annie took me to lunch and asked if I wanted to go to a Renewal retreat workshop for prayer leaders with her in Connecticut. The brochure she handed me said things like, “Prayer can connect us to our Living Source and to each other, enfolding us in love and praise, wonder and gratitude, awe and thankfulness.” I told her I really didn’t think that sort of thing was for me; I had been leading services with her for almost eight years, but that didn’t mean I’d become more spiritual. It just meant that I had gotten better at leading services. I told her that when it comes to God, I have no clue what I believe. But she told me that’s OK. “I believe in angels,” she said. “And you’re not in a place where you know what you believe about God. I promise you there will be people there who also believe in angels, and there will be other people there who have no idea what they believe about God. It’s not about either one being right or wrong. It’s about deepening your understanding of where you are.” So, I agreed, and we were on our way to Connecticut.The workshop proved to be the most transformative Jewish experience of my life. Three times a day, we took turns leading each other in prayer, and then we would deconstruct the experiences in big master classes. I had never experienced prayer like this. People led with nusach, yoga, shruti box, gongs, ancient melodies, Joni Mitchell melodies, melodies that could rip your heart wide open and leave a beautiful scar, poetry, silence, and above all, total vulnerability. I found myself in a community of Jews with backgrounds I could never have imagined. My Southern Jewish Reform world had just exploded wide open, and I was soaking in every beautiful second. The first day back on my job as a public school teacher, we stood in small circles around the school cafeteria and were asked to say our names and a color to describe how we felt. When it was my turn, I lifted my palms up toward the sky, a genuine smile breaking out on my face, and heard myself say, “sunrise yellow.”From then on, I’ve been comfortable identifying as spiritual. I began to value leading services from a place of deep authenticity and vulnerability. While my Jewish life was going through a spiritual awakening, however, my romantic life was collapsing. My girlfriend and I were on our way to a long, messy, complicated breakup. Even though our relationship was good, I always felt like I had more self-exploration to do, and I never felt settled. I seriously wondered if I was a gay man who hadn’t accepted myself yet, even though men were of little romantic interest to me. As things neared their end, my now-ex-girlfriend said to me, “I have never met someone who knows themselves as little as you know yourself.” I knew she was right. I knew that before I could be in a relationship again, I had more to learn about myself.In 2018, a friend and I started attending a weekly group for gay-identifying people in need of some emotional support. I kept going with them, even though I didn’t really understand what identity qualified me to be there. I still identified as a man who was mostly attracted to women, but for some reason, I felt like I belonged in that group. Slowly, I began to question if the root of my struggle wasn’t about the gender of those I was attracted to, but about my own gender. I had no idea what to do with these new thoughts. I had spent 26 years on Earth not identifying as transgender, I didn’t think it made sense for me to start now. It seemed like people who were “really” transgender knew earlier in their life than I did, so I assumed that that couldn’t be me.Either way, my new friend helped me out by giving me makeup tips on the weekend, going shopping for women’s clothing with me at thrift stores, and giving me some of the clothes they no longer wore. That semester, I really got into dolling myself up on the weekends in the privacy of my own home, and one day I had the courage to go to the grocery store in makeup and a skirt. I was sure I wouldn’t see anyone I knew, so of course I ran into a colleague from work. Hiding my sheer terror, I managed to exchange pleasantries with him and even laugh about some work thing, before coming home unscathed with groceries in tow.Looking back at how my journey through gender has unfolded since then, I’m reminded of the list of dayenus that we share together on Passover. “If God had given us Shabbat but not brought us to Mount Sinai, it would have been enough! If God had brought us to Mount Sinai, but not given us Torah, it would have been enough!” At every step, it sounds like enough would have been nice, but each one unlocks a new element that today we consider central, and often indispensable, to Jewish identity. We really sing that “if God hadn’t given us Torah? That would have been enough,” even though it’s central to our Judaism today. Dayenu stayed with me on my journey, reminding me to enjoy each new self-discovery and to be unafraid of leaning into the next one.That winter, I attended a Jewish communal singing workshop on the Upper West Side of Manhattan. I went expecting to learn about the pedagogy of communal singing while enjoying a trip to the Jewish American homeland. When I arrived, I found that even though this was neither an event for queer people nor a workshop focused on queer issues, it just so happened that I was about to spend the week surrounded by visibly queer Jews under 30 years old interested in observant lives and communal singing. Suddenly, I found myself in a room with a number of queer-identifying women with shaved heads and tzitzis.I had come to New York bringing only men’s clothing—my button-down shirts with buttons sewn into the right-hand side were a staple of my wardrobe. Upon arrival at the shul, I was immediately drawn to one woman in particular. She was about my height, with short blond hair, wearing a long blue blouse. She radiated joy and confidence. I sensed that we were both travelers on similar journeys, and, unlike me, she was already living her truth out loud. Being around her made me realize that the only reason I didn’t pack blouses or dresses or anything like that in my suitcase was because I hadn’t given myself permission. One look at her, and I instantly knew that she was wearing what I wanted to be wearing. She was presenting what I wanted to be presenting. She was living on the outside what I had only been living on the inside. Wherever I was in my journey, it suddenly felt like not enough. Seeing her made me realize that I could express myself however I want. All I had to do was give myself permission.I had more dayenu moments. If I continued to amass dresses and makeup but not ever wear any of it outside the house, it would have been enough. If I wore them outside the house but never while serving a congregation in the role of cantorial soloist, it might have been enough. On the Friday after Purim, I texted the rabbi at the synagogue where I was the cantorial soloist that night. I told him that I was going to come dressed in feminine attire and wearing makeup. He had no problem with it. Later that evening, I arrived quite proud of my increasing wingtip eyeliner proficiency. Before anyone could offer a confidence-boosting compliment, a congregant came up to me and asked, “Are you still dressed up from Purim?” I responded politely and awkwardly, “No?” “Oh,” she said, and walked away.I began to wear makeup to the services that I led at Temple Sinai more frequently. Every time I wore what I really wanted to wear, I was nervous, but I was always received by the congregation with overwhelming love and support. When people asked me if there was a reason for the change in appearance, I told them I was “just trying something new.”I started using the name JB and they/them pronouns around this time. J and B are my first and middle initials, and one morning it dawned on me that they make for the androgynous name I’d always been looking for. If I had discovered my new name but not changed my pronouns, dayenu, it might have been enough. I was through pretending that I enjoyed being referred to as “he,” but I wasn’t comfortable asking anyone to call me “she.” At this point, I was only vaguely aware that there were people who preferred the singular pronoun “they,” but I didn’t personally know anyone who did. I was also convinced that I couldn’t be a member of the transgender community because the arc of my gender journey didn’t line up with all the other transgender narratives I’d heard before. Stories such as “I am definitely a woman,” “I feel like God made a mistake,” and “I knew I was transgender from an early age,” didn’t resonate with me, so I assumed I had no place among trans women. I was treating these narratives that I only knew from mainstream media as if they were a transgender community requisite checklist. Meanwhile, every time I said nothing when someone said, “How can I help you, sir?” felt more and more like an act.During the rest of the week, I was still teaching choir and managing a mostly masculine wardrobe with an increasingly feminine presence. My presentation in the world at the time was definitely androgynous, but I no longer saw myself as an “androgynous boy,” because I no longer saw myself as a “boy.” I was ready to do everything I could to free myself from the label of “man” without fully diving headfirst into the label of “woman,” even if I wanted to present feminine. Even though I was comfortable with someone referring to me as “she,” I knew I still came off as a feminine boy. I didn’t want to impose that cognitive dissonance on other people by insisting that they refer to me as she, especially when everything felt so new to me. It’s confusing, I know. But the closer I got to discovering a label that matched who I knew I was, the more I cared about getting it right. The confuser finally became the confused.In 2019, when I discovered Jacob Tobia’s autobiography Sissy: A Coming-of-Gender Story about their nonbinary identity, for the first time I felt like I was reading a book about myself. In it, Jacob, who uses the pronouns “they” and “them,” describes gender identity assigned at birth as being akin to a sweater that an aunt might give as a gift for the holidays. It may have looked cute, felt comfortable, and made other people happy to see you in it when you were a kid, but as you grow up, it starts to feel like it’s not for you, it’s ill-fitted, and it just no longer serves you.Reading Sissy was an important step on my journey. It made me feel like there are words out there that describe who I know I am. It made me feel like I belonged. I began coming out as gender nonbinary and trying out the pronouns they and them, and for the first time, I was actually less confused. I found a gender identity that felt like home, like a new sweater that was comfortable enough to wear around the house and that I wanted to be seen in by others. With a new name, new pronoun, and 15 new pairs of size 13 women’s shoes from a Payless that was going out of business, I left for a summer internship in New York City.Spending a summer in New York gave me a chance to get comfortable in my latest dayenu. For the first time ever, I wore heels and a dress to shul. Then I did it again. And again. And again. I had worn feminine shirts and pants to services in Houston, but for the first time—wearing 2-inch heels and a floral print dress to the crowded sanctuary of B’nai Jeshurun on a Friday night, I felt like I had shown up wearing on the outside what my soul looked like on the inside. I knew that I would never again want to attend a service somewhere that expected anything less.Back in Houston at the beginning of August, it was time to prepare for the High Holidays. I began to consistently present feminine when I would lead services at Temple Sinai. After services, people would tell me they loved the new looks—some even asked for makeup tips! I also began to notice a few more people attending the service who looked like me. I noticed genderqueer people choosing to come to services more and more often.One Shabbat evening, a woman in her 70s approached me and my trans friend and shared how glad she was that young people felt comfortable exploring gender like this nowadays. She told us that when she was in her 20s, she wasn’t comfortable with being a woman. She wanted to know what it would be like to be a man, dress like a man, and assume male roles in society. Whenever she told anyone, they laughed at her and made her feel like the barrier was impossible to cross. Her culture never let her live any of her gender nonconforming identities out loud. She was so glad that my friend and I were able to live out ours.Not everyone at the synagogue was kind about how I was suddenly leading services in makeup and heels, though. While no one ever aimed their unkindness directly at me, Rabbi Annie told me stories about how a few members were revoking their membership and citing my appearance choices as one of their reasons. As Rosh Hashanah drew closer, one made nasty phone calls to other congregants about me. Others got in shouting matches during temple events, but still no one confronted me directly. When things like this happened, Annie stood up for me and the queer community on every single occasion. Temple Sinai then lovingly asked me if I would write about my transition to the congregation in a letter before the holidays. They wanted to help ease any shock that those who hadn’t been to services since last Yom Kippur may experience upon seeing my new look. While I know I could have chosen to not write that letter, I decided that it was what I wanted to do. I told the congregation, “I have a sacred obligation to show up as me in case that leads somebody else to give themselves permission to show up as themselves.” Following the letter’s publication, accompanied by one signed by the temple’s board members, an anonymous donor gave $20,000 to the synagogue in support of the rabbi’s inclusivity.When the holidays rolled around, I wore my new blouse, flats, makeup, and, for the first time at High Holidays, no tie. I did it because I decided that was how I could show up as myself. The holidays are a huge spectacle at synagogues, drawing members we only see once a year and throwing open the back walls of our sanctuaries to handle the overflow crowds. But they are also the time when we own up to our shortcomings in the presence of Avinu Malkeinu (Our Father, Our King—or whatever understanding of God works for you). Chanting Kol Nidre, I felt more worthy of being the messenger of prayer than ever before. On the holiest day of the year, I stood in front of the congregation wearing my soul on the outside and praying that, dayenu, it would be enough.For a nonbinary person, Jewish prayer life can be tricky at times. I can’t even say the first word of the first morning prayer without running into a challenge. Today, should I say modah ani (feminine) or modeh ani (masculine) as I give thanks for the daily restoration of my soul? I always start by trying modah, which feels more right than modeh, then I often give modeh another shot to see if today it may feel more right than yesterday. It never does.I haven’t stepped foot inside of a davening space with a mechitza in years, even though my interest in traditional Judaism has grown. I imagine that if I did, I would know that since I wouldn’t be able to “pass” as a woman, I would relegate myself to the men’s side, just like filling out an official government form with only two gender options. A friend of mine recently invited me to join her on a Friday night at Chabad. As much as I would love to have that experience, I wouldn’t be fully comfortable in either section. The problem also came up when I filled in as a lead singer in a local klezmer band for an Orthodox wedding. I went to all of the rehearsals wearing makeup and a shiny dark purple nail polish. As the wedding drew closer, I knew the point would come where I would need to ask the leader of the band what she thought I would need to wear, even though I already knew the answer before I asked. We agreed that in the interest of making sure that no one would throw me out, I would have to scrub the polish off my fingernails and put on a black suit and tie for the joyous occasion. At the wedding, the kahal spontaneously burst into a joyful niggun in between each of the sheva brachot, and I dreamed of a future where I could have a wedding that also married the joy and authenticity of living as a nonbinary person to the naches of a traditional Jewish community.During Pride Month in 2020, I had the pleasure of watching the livestream of the Trans/Nonbinary Pride Shabbat from Congregation Beit Simchat Torah, the LGBTQ synagogue in New York City. Hebrew Union College cantorial student Ze’evi Berman, who also identifies as nonbinary and uses the pronouns they/them, led most of the prayers. Toward the end, they offered their own musical setting of the priestly benediction, which they titled “Y’varechecheh: A Nonbinary Blessing,” which blessed the congregation using queer-inclusive, gender-neutral Hebrew. They sang “Y’varechecheh Adonai v’yishmerecheh,” and I teared up as I sensed my mind growing lighter. Singing and praying in gendered Hebrew had been weighing me down and I hadn’t even noticed it until I experienced its absence. Nonbinary Hebrew drew me closer to my Judaism and to God because I didn’t have to choose which inexact version of me—boy or girl—I wanted to pray from.Now that I have found a gender identity that fits, I have had an easier time understanding how my identity fits into the transgender/gender nonbinary umbrella of identities. My friend with whom I went to the group for gay-identifying folks a couple years ago has now introduced me to several other queer friends with whom I’m totally at ease being myself. In Houston, I’ve been able to find queer community, but I’ve had a much harder time finding queer Jewish community. While Houstonian queer Jews exist, my travels to New York City have left me longing for a community like the ones I’ve experienced there. I’ve gone to the Jewish Communal Singing workshop twice now, and both times I spent my Friday night at CBST. Surrounding myself with fellow queer Jews as we sing our way into and out of Shabbat is where my soul feels the most at home.