Yiscah Smith shares her story at Ner Shalom in Cotati, the first of three talks in the North Bay. (Photo/Shoshana Hebshi)
Yiscah Smith shares her story at Ner Shalom in Cotati, the first of three talks in the North Bay. (Photo/Shoshana Hebshi)

In Sonoma, trans Jewish scholar talks about her journey to ‘authentic living’

To live a life of authenticity, ignore the various strings tugging in all directions and instead listen to the soft, inner voice that leads to one’s true path. So says Yiscah Smith, a trans woman who spoke at Congregation Ner Shalom in Cotati on June 13 during a three-day scholar-in-residence program.

Titled “Spirit, Gender and the Quest for Authentic Living,” the program saw Smith, who lives and teaches religious text and spirituality in Jerusalem, give lectures at three Sonoma County synagogues.

In the first, titled “40 Years in the Wilderness: My Journey to Authentic Living,” Smith told her personal story to a packed house at Ner Shalom on what happened to be her 67th birthday. She began with a three-minute meditation, asking attendees to practice mindful breathing while pondering a question: What would it be like to be more like the person you believe you’re supposed to be?

“What would that feel like?” she probed.

After introducing some quotes from some of her favorite Jewish scholars, including Rabbi Abraham Joshua Heschel and Rav Kook (Abraham Isaac Kook), Smith began an abridged retelling of her lifelong journey toward living authentically as a woman — abridged so the audience wouldn’t be there until midnight, she quipped.

Born in 1951 as Jeff, who later become Yaacov after marrying a woman and becoming more religious, Smith grew up in a secular Jewish family on Long Island and remembers the pivotal moment when she realized she was different. She was 5. One evening, watching her mother prepare to go out for the evening, she became entranced. “When I grew up I knew I wanted to be just like her,” she recalled.

Smith’s mother responded by telling her little boy to go into the bathroom to watch his father shave. “I was so confused,” she told the audience. “I asked her, ‘Why?’ and then I asked myself, ‘What part of me would rather watch my father shave?’ [Mom] answered with absolute surety: ‘Because you are a boy.’”

From this early experience, Smith began to feel the pull of society’s expectations and a tug away from what she intuitively understood as being a girl trapped in a boy’s body. “How everyone else saw me, I surely did not,” she said.


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This was the beginning, Smith said, of living an untrue and secretive life.

Smith’s story then fast-forwarded to age 20, when she traveled to Israel to work on a kibbutz and paid a visit to the Western Wall. Living outwardly as a boy, she was confronted by the choice to approach the Wall from the men’s side or the women’s side.

“I have to choose — am I a male or a female — to go further. What do I do? So simple for most people and heartwrenching and anything but simple for me,” she said. “I almost turned around and left to avoid to going through that horrific pain. I said if I choose to enter on the women’s side, which is where I knew I belonged, I will cause this unwanted attention, which I definitely didn’t want to do. If I chose to enter on the men’s side, [because] the world was telling me I’m male, if I choose to obey that, then I will experience feelings of self-betrayal. Whatever I did was the wrong choice.”

A stronger voice inside told her to touch the stones. She entered on the men’s side, touched her head to the cold stone and felt a spiritual awakening. “I felt grace,” she said. “I felt something other than hate. It was as if I felt home. It was where I was supposed to be. I later came to learn what I was feeling was my soul, my spiritual center. I got in touch with something that defied gender identity dysphoria.”

From that moment, Smith said, she wanted to learn all she could about Judaism, about Torah, about Israel and everything in between. She moved back to New York to study and immersed herself in the world of Orthodox Jewry, in Chabad, in Lubavitch. As a man, she dressed in the traditional black coat and hat. She believed that if she was a dedicated Jew, God would ease her struggle. But the quiet self-loathing and despair did not recede.

At age 34, Smith moved with his wife and six children to Jerusalem to become the director of the Chabad center in the Old City. “The more I succeeded outwardly, the worse I felt inside,” she said. “I wanted so much to fail because then I thought God would finally put me in my place, so to speak. And God did.”

In 1991, during the first Gulf War, Smith had a “spiritual breakdown,” she said. “I said to God, ‘I can’t do this anymore. There’s nothing left inside.’ I was numb.”

She turned 40 that year and the facade began to crumble. She said after trying so hard to live “someone else’s life” she was so distraught that she left Israel. She divorced and moved back to the United States, and for 10 years bounced from job to job. She stopped teaching Torah and halted her involvement with the Jewish world.

How can I be authentic in a world that doesn’t encourage me to be authentic?

“I asked myself, ‘How can I be authentic in a world that doesn’t encourage me to be authentic?’”

On her 50th birthday in 2001, feeling as if she had no more energy to go on living as she had been, she decided to start her journey toward a gender transition.

“My life became illuminated,” she said. “This was the birthday gift I gave myself. Authentic living, to me, meant no longer living in fear with the shame or the guilt that accompanied my life of infidelity to myself.”

She returned to Israel and to the Western Wall on her 60th birthday, now as Yiscah, and realized it had taken her 40 years to cross the barrier between the men’s and women’s sides. It was her own 40 years of “wandering in the desert” and it became the title for her book, “Forty Years in the Wilderness: My Journey to Authentic Living.”

Smith read a chapter from the book at Ner Shalom, then took questions from the audience: How did her children and parents react to her transition? (Mixed, she said). What was it like returning to the Jewish community? (No fear). “It feels so right to be a part of the change happening in Jerusalem,” she added, alluding to strides being made by progressives and LGBTQ people there. “I love being Jewish now more than ever before. I also feel part of the world.”

Smith traveled to Congregation Beth Ami in Santa Rosa for her second lecture, “Jewish Living as the Cultivation of a Spiritual Practice,” and concluded the series with a talk at B’nai Israel Jewish Center in Petaluma called “Lech Lecha: Go to Yourself: Moving from One Self to Another Self.”

Carol Appel, the Sonoma County concierge for the S.F.-based Jewish Community Federation, said Smith’s visit was the result of three congregations working in tandem — a collaboration she loved to see.

“Yiscah Smith is an important example of the diverse and inclusive community in Sonoma County,” Appel said. “I think she’s a reflection of what our Jewish world is today, in the Bay Area and in the world.”

Shoshana Hebshi
Shoshana Hebshi

Shoshana Hebshi is a freelance writer and former J. copy editor living in the North Bay.