The Hebrew month of Elul has begun. A pensive time, a reflective time, a time of Torah study—the month is an intense preamble to the High Holidays. As a friend once told me, think of Elul as the month in which you train for the marathon that is the Days of Awe.

In homage to this month of Elul, each day we recite Psalm 27 from the first day of Elul through Hoshana Rabbah on Sukkot. Within the psalm is the familiar verse, “One [thing] I ask of the Lord, that I seek that I may dwell in the house of the Lord all the days of my life, to see the pleasantness of the Lord and to visit His Temple every morning.”

Each of Elul’s 29 days also begins with a blast of the shofar. We need to be “woke” in Elul—a month during which we should be hyper-aware of issues concerning social justice and racial equality. That is the precise intention of a project called “Jewels of Elul.” The brainchild of Los Angeles-based musician and activist Craig Taubman, the idea is to focus one day at a time on each of the 29 micro-essays of wisdom and reflection collected in the eponymous booklet. This year’s contributors include comedian Sarah Silverman and her sister Rabbi Susan Silverman, Jonathan Greenblatt, CEO of the Anti-Defamation League, and Yossi Klein Halevi, writer and peace activist.

“Jewels of Elul” began 13 years ago when Taubman was commissioned to write a melody for Psalm 27. He wondered if he could expand upon that Elul feeling. His concept was straightforward—29 contributors, including public figures and various writers, would write 250 words each on a given theme.

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In a recent telephone interview, Taubman told JewishBoston: “Compiling ‘Jewels of Elul’ presented a wonderful opportunity to use Jewish ideas to express healing, hope, change and renewal. Over the years we’ve had various contributors, from Elie Wiesel to Lady Gaga, Jeffrey Katzenberg to the Dalai Lama, and Barack Obama to John McCain.”

For this year’s project, contributors were asked to riff on the theme and possibilities of “What If.” It’s a powerful premise that is especially illustrated in an achingly poignant entry by Ellie Schneir, a Los Angeles County public defender and suicide prevention activist, whose 14-year-old son, Matthew, ended his life seven years ago. In a heartbreaking progression of “what ifs,” Schneir asks: “What if the presence of God that stayed Abraham’s hand to spare Isaac was able to catch my son as he fell 10 stories? What if Matthew had been able to graduate from high school? College? Marry? Become a parent? What if Matthew had lived?”

Transgender activist Abby Stein asks the straightforward question: “What if by chance we were born/lived in a different way?” Stein writes that as a public educator and activist who lived the first two decades of her life as a Hasidic man, she often gets asked: “What if you would have been born into another Jewish community? What if you would have been raised with a different religion? What if you could’ve been born in a female assigned body at birth? What if you were LGBTQ, white, rich, poor, or skeptical of religion?”

Sarah and Rabbi Susan Silverman offer a dialectic on fear and risk-tasking. Sarah asserts: “Fear turns the future into a ghost story. If we gently remind ourselves, ‘Yo, self, that’s your fear of the unknown talking,’ we could make room for ourselves and others to take risks, to become and create.” Susan responds: “What if more people asked a different kind of ‘What If?’ Not, ‘what if something horrible is sure to happen,’ but ‘what if anything is possible?’ Absolutism could melt into possibility. Our worldviews would not depend on the falseness of others. We would not cling to the image of a Zero-Sum God but to holy complexity.”

Taubman lauded the diversity of the written contributions in “Jewels of Elul.” He said: “The point is to see things through a variety of lenses, including Jewish, politically conservative or liberal, and even a non-Jewish perspective. We are open to everybody from different walks of life. If we pleased everybody, in all likelihood we wouldn’t say anything that had much value. The time leading up to the High Holidays should be hard work.”

That hard work can begin with the ADL’s Jonathan Greenblatt’s supposition that, “If we could start with our own questions, probing biases we unintentionally carry and choosing to act intentionally to address those misperceptions and prejudices that underlie them, I believe the answers would help us to make powerful strides in this journey towards creating a more just and equitable world.”

What do you say, JewishBoston readers? What if you could change one thing in the world? What if you could resolve a personal conflict? What if you had the power to solve one world problem? What if, what if, what if? The possibilities are daunting and limitless. Let us all stay woke in Elul and beyond.