This one-soul-to-another book feels like it absolutely had to be written, and there are many sentences that, taken alone, are moving contributions to Jewish thought. For readers who have experienced doubt, non-interest in Jewish tradition, or simply bafflement at what is really going on, Lew is an ideal companion.

Lew readily admits his defeats and limitations as both a rabbi and a human being, and this makes his writing on repentance palatable and intimate. Here is a rabbi who repeatedly says that he is not perfect in his faith or his life. He did not begin life as a religious believer, but has lived as a seeker who can report back on his voyage to greater understanding.

For Lew, the great annual voyage of the Days of Awe begins early. Instead of starting his chronicle of the arc of repentance with Rosh Hashanah, Lew begins with Tishah B’Av, the fast day and date of the destruction of both Temples. Slowly, with many asides into personal stories, Hebrew texts, poems, cultural and political references, and comments of other rabbis from various eras, Lew probes how late summer and early autumn are a time of questioning in Jewish tradition.

For starters, Lew presents two ways of looking at the Ninth of Av—as a "cursed time," and as a time when we are reminded that catastrophes will recur until we get things right.

This is true in our personal lives as well, the commentator Rashba notes, since we find ourselves in the same situations over and over. Lew moves that observation further, asking, "Why do our relationships always fail in precisely the same way?" He then pushes, writing,"What is the recurring disaster of my life? What is it that I persistently refuse to see?"

Lew’s big strength is his ability to tie Jewish tradition to individual concerns. He explains that Kol Nidrei, the prayer in which we renounce all our vows at the start of Yom Kippur, "begins at the moment of heartbreak." As Lew writes, "the tragic pain of the soul—the pain we hear in those first grieving notes of Kol Nidrei—is the pain of loss, the pain of impermanence."

Our evanescence, Lew thinks, is often our greatest problem.We use it as an excuse to remain all potential. "Many of us are afraid to be who we really are, precisely because we sense this," Lew writes."We sense that once we have risen up, we will begin to fall away."

In haunting moments like this, Lew’s book becomes hopeful and encouraging. In detailing the voyage of the soul that Jewish tradition acknowledges, he offers the reader exactly what the Days of Awe have represented from ancient times through the present days of uncertainty: the hope of understanding, and finally, a truer life.

Aviya Kushner is a poet and journalist. Her work has appeared in Harvard Review, Partisan Review, and the International Jerusalem Post among other publications.