There is a lot of talk about “Jewish journeys” at Limmud. But few have travelled a path as difficult and poignant as Yiscah Smith, a spiritual teacher from Jerusalem who lectured on Chasidic thought at the conference.

Born Jeffrey Smith in America, and outwardly a man, for 50 years she wrestled with the inner turmoil of feeling more a woman.

On her first visit to Israel at the age of 20 in 1971, she felt “even more conflicted” when she came to the Western Wall in Jerusalem.

“No matter what side of the mechitzah I went on, it would be the wrong choice,” she recalled in a talk about her life in which she read extracts from her recently published memoir, Forty years in the Wilderness; My Journey to Authentic Living.

“I knew I belonged on the women’s side.”

For many years, she believed her predicament unique. “I really believed I was the only person that would look in the mirror and see something different looking back at me.”

Not from an observant family, she became religious, settled in Israel, married and raised six children. She worked for some years for Lubavitch in Jerusalem.

But by her 40th birthday in 1991, she was alone and feeling that there was “no place for me in Israel – that was probably the darkest cloud I ever had to face.”

It took another 10 years, when spiritually at rock bottom, that she made the decision to become the woman “I always knew I was...destined to be.”

Her resolve to undergo the process of transition – which took four years to complete - was the “dawn of my own personal redemption”.

But it also signalled spiritual regeneration. Just as the ancient Israelites had cried out to God from the midst of slavery in Egypt, so she felt that God heard her from “a place of utter helplessness and desperation”.

Her attempt to lead her life as a man had left her worn out and embittered. But now, she recalled, “I awoke from this dark sleep to sense God in my life.”

The first time she lit Friday night candles as a woman she felt as if “I went to the next world”.

When she returned to live in Israel in 2011 now as Yiscah (Jessica), she went to the Kotel to thank God, this time to pray in the women’s section. “I went up to the stones and started to cry.”

It took a while for her mother in America to feel ready to meet her after her transition, but when she did, she remarked that she saw something in her eyes that she had not seen before: peace.

Then she said to her, “I don’t like your outfit – let’s go shopping.”

Not all of her family are reconciled. Only one of her six children, who is a rabbi, is currently very close to her.

But she said, “If I can believe in Moshiach, I can believe my kids will be back in my life.”