Yiscah Smith is 64 years old. She lives in Nahlaot, in Jerusalem. But her journey to this Orthodox-meets-hipster neighborhood took her through what seems like four lifetimes. She was born in Long Island, as Jeff Smith, to a Conservative Jewish family. Jeff married a woman, they became more religious, made aliyah, and had six children. Jeff became Yaacov. A few years later, Yaacov’s identity began to unravel, presenting a terrible dilemma: What do you do when you realize that in order to be true to yourself, you have to shatter everything around you, including the lives of those you love most?

This is Yiscah’s story, as told to reporter Molly Livingstone. Yiscah is the author of Forty Years in the Wilderness: My Journey to Authentic Living and was a popular speaker at TEDxJerusalem in May 2015.

Music for this episode comes from Blue Dot Sessions, Dana Boulé, and BenSound.