In 1975, 24-year-old Yaakov Smith made a deal with God. “I will be as devout, as dedicated, as ultra-Orthodox as I can be, if you can do me one favor: When I wake up tomorrow morning, either let me feel like I’m a man, or let me have the body of a woman. You choose.”

When Smith relates this moment to me more than 40 years later, it is no longer as Yaakov, but as Yiscah. At 50 years old, Smith finally made the decision to transition. “I kept my end of the deal, but God did not keep His,” she said at a lecture in 2015. Now she lives in Israel and works as a Jewish educator at the Pardes Institute of Jewish Studies. She has her own practice as a spiritual mentor and lectures around the world on authentic living and spirituality.

The Transition Years

At just 5 years old, Smith knew that she had been born into the wrong body. Watching her mother apply makeup in their Long Island home, Smith gazed, transfixed, until her mother disrupted her reverie. “Why don’t you watch your father shave?” her mother suggested. Smith immediately intuited that living as anything but the gender into which she was born must remain a secret.

The years that followed were filled with as much spiritual turmoil as questions of gender identity. After briefly living in Israel, Smith became interested in traditional Judaism and moved to Crown Heights, Brooklyn, the epicenter of the Chabad movement. Smith’s wife was also newly observant through Chabad, and they started a family. In 1985, their family of eight moved back to Israel, where Smith became director of the Chabad center in Jerusalem.

As a natural educator, Smith’s programming was immensely successful — but it came at a cost. “I was teaching the truth, but not in truth,” she explains. “It was draining me.”

What Smith calls a spiritual breakdown came in 1991. Feeling guilty for lying to her family about who she really was, Smith divorced her wife — a choice that ultimately forced her out of her leadership role at the Chabad house — abandoned Jewish observance, and moved back to the United States.

By her 40s, Smith had a computer and was finally able to put a name to her gender dysphoria; online support groups showed her for the first time that she did not suffer alone. It wasn’t until her fiftieth birthday, though, that Smith finally made the choice to transition from Yaakov to Yiscah. She recalls a particularly dark day when she finally denounced her previous deal with God that she had made in Crown Heights many years prior.

“God,” Smith began, “No more deals. You’re in charge. Just help me live the truth.”

A New Beginning in Seattle

With the decision to live as Yiscah, Smith also wanted to return to traditional Judaism. “It was, if not more of, a spiritual transition than a gender transition,” she says. She chose Seattle as her next stop in order to live in a place where no one knew her from before.

Smith became active in Shaarei Tefillah Lubavitch, a Chabad synagogue in North Seattle, though she no longer identified with the Hasidic sect. Smith enjoyed meals at community members’ homes and even began teaching classes again. “I had this image that I would transition, stay low profile, and just mix into the world,” she says.

But Smith’s friends in the neighborhood knew her story, and they wanted her to share it widely. After three friends encouraged Smith, separately and on the same day, to write a book, she resolved to listen. Her self-published memoir, Forty Years in the Wilderness: My Journey to Authentic Living, came out in 2014.

Coming Home

In 2011, Smith returned to Israel, where she currently resides. By that time, LGBT visibility in Israel was increasing. Over 100,000 people turned out for Tel Aviv’s annual Pride Parade that year — the largest pride event in the Middle East and Asia. Two years later, the Knesset would pass a bill removing the requirement to list gender on Israeli identification cards in light of the complications it posed for the transgender population. While exact figures of the transgender population in Israel are unconfirmed, it’s been estimated that they comprise at least 0.5 percent of the population.

In 2015, Smith gave a TEDx Talk in Jerusalem about her transition to a crowd of over 800 people. It was marked by two sets of applause and a standing ovation. Nonetheless, attitudes among Jewish leaders toward the LGBT population in Israel are split. In April, after a transgender high schooler was violently beaten and bullied in Ashkelon, 56 rabbis signed a letter calling for tolerance. Yet over the summer, Israel’s education minister endorsed the possibility of conversion therapy, the widely condemned practice of changing one’s sexual orientation.

Smith is now focused on expanding her reach as a mentor. Her classes at the Pardes Institute are well attended by students of all ages throughout the year; she is most known for her classes on Jewish meditation and spiritual Torah. A forthcoming documentary reflects her priorities. Titled I Was Not Born a Mistake, the film follows Smith’s life and weaves in lectures she’s given around the world. It’s slated to screen at the Jerusalem Jewish Film Festival in December and then on Israel’s documentary network.

Smith’s growing renown often leads others who are on their own journeys to seek her counsel. And though she prefers to avoid denominational labels, her position as a well-known Jewish educator among the observant population prompts people to ask how she received the rabbinic approval to honor her gender identity.

“In our tradition, the value of a life is very high,” she tells them, referring to the concept of pikuach nefesh, or saving a life above all else. “I never felt that I had to go to a rabbi for permission to save my life.”

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