Uber, as you may have heard, has been a very naughty company, doing anything from sabotaging its competitors with phony ride requests to evading law enforcement operations with shady electronic gadgets. Add to that allegations of sexual harassment and a chief executive behaving very badly, and you’ll understand why the company eventually had no choice but part ways with its boss, Travis Kalanick, and search for a new executive.

The new CEO, Dara Khosrowshahi, took the wheel this month. And in one of the most inspired—and inspiring—moves in recent Silicon Valley history, the Iranian-born Khosrowshahi, the former head of Expedia, taught his colleagues, not a crowd usually prone to introspection, how to do Teshuva.

“I have to tell you I am scared,” he wrote in a memo to his former employees at the travel site. “I’ve been here at Expedia for so long that I’ve forgotten what life is like outside this place. But the times of greatest learning for me have been when I’ve been through big changes, or taken on new roles—you have to move out of your comfort zone and develop muscles that you didn’t know you had.”

It’s rare that you think of tech entrepreneurs and great rabbis in the same context, but Khosrowshahi’s heartfelt admission of vulnerability reminded me of a favorite story about Rabbi Joseph Dov Soloveitchik. A few weeks before Rosh Hashana in 1967, the story goes, the rabbi’s students asked him about the meaning of true Teshuva. Rather than quote the scriptures or cite some rabbinic opinion, he told them a very personal story. The previous winter, he said, he was at home in Boston when a storm started raging outside, blowing his windows open. The rabbi ran all around his house, closing his windows and bolting them, making sure the house stayed warm and dry. Then, he went upstairs to check on his wife, who was very ill, to see if she needed an extra blanket or a pillow. When he got to her bed, it was empty. It was then that the rabbi remembered, he said, that his wife had died the month before. Stricken by grief, he refused to accept the reality of her death. But now, standing by the made bed, he understood that his denial was just a way for him to avoid dealing with harsh and unpleasant and frightening thing. And this realization, he concluded, was what Teshuva was truly about.

So this month of Elul, as we slouch towards the High Holidays with their call for repentance and occasion for rebirth, let’s hope more of us follow Khosrowshahi’s lead and begin the new year by admitting that we’re afraid and that it’s time to wake up to new realities.





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