What to Read for Your Teshuva Prep

10 Books to help you prepare for the Jewish new year

As the Jewish year draws to a close, we find ourselves in a season dedicated to reflection and renewal. The Days of Awe, the period from Rosh Hashanah to Yom Kippur, call us to engage in teshuva—a word often translated as "repentance" but more literally—and perhaps more accurately—understood as "return." It is a return to our most authentic selves, a journey back to the core of who we are meant to be, closer to God, and more attuned to our deepest values.

This year, our need for this return feels more urgent than ever. The events of October 7 have left many of us searching for meaning in a world that suddenly feels uncertain. We are seeking connection—not only with the Divine but also with our fellow Jews, our families, and the person we know we could be, in a higher, truer form. In these times, we are reminded that teshuva is not just about individual reflection but about a collective yearning for a renewed sense of purpose and unity.

If you’re looking for guidance on this journey of return, these books offer wisdom, insight, and inspiration. They invite us to explore the depth and breadth of what teshuva means—to ourselves, to our communities, and to God.

Letters to a Buddhist Jew by Rabbi Akiva Tatz and David Gottlieb

A profoundly moving exchange between a Jew exploring Buddhism and an Orthodox rabbi. Through their heartfelt letters, David Gottlieb raises challenging questions about faith, and Rabbi Akiva Tatz responds with profound wisdom and empathy. This book offers a genuine and insightful dialogue that will touch anyone on their own spiritual journey.

100 Shofar Blasts by Rabbi Bentzion Ettlinger

A treasure trove of inspiring stories and fresh insights featuring Rabbi Bentzion Ettlinger’s personal experiences as a bal tokeia (one who blows the shofar). It’s a deep and heartfelt exploration that will deepen your appreciation for the mitzvah of shofar.

Seek My Face: A Jewish Mystical Theology by Dr. Arthur Green

A book that uniquely charts a course through the vast landscape of Jewish mysticism, offering a fresh, deeply personal guide for anyone seeking to understand God's presence in the world and within themselves.

Here All Along: Finding Meaning, Spirituality, and a Deeper Connection to Life—in Judaism by Sarah Hurwitz

After a successful career as a political speechwriter for high-profile figures like Michelle Obama and Hillary Clinton, Sarah Hurwitz found herself unexpectedly drawn to Judaism during a personal crisis. Her book explores how the rich, transformative insights she discovered can bridge the gap between Judaism’s depth and its often superficial practice, aiming to inspire others to engage deeply with their faith.

My Bright Abyss by Christian Wiman

With a blend of joy and sorrow, Christain Wiman explores how contemporary spirituality can engage with both modern thought and religious tradition, offering a timeless exploration for those grappling with the boundaries of existence and the enduring question of the divine.

If All the Seas Were Ink by Ilana Kurshan

A story of finding unexpected strength in sacred texts, of discovering humor in hardship, and of slowly stitching a new life together with the thread of tradition. For anyone who’s ever needed a way back to themselves, this is a book that offers companionship and hope.

Essentialism: The Disciplined Pursuit of Less by Greg McKeown

A book about focusing on what truly matters by eliminating what doesn’t, and finding clarity and purpose in everyday life.

The Power of Now by Eckhart Tolle

A transformative journey toward enlightenment, The Power of Now teaches readers to break free from mental limitations and connect with their timeless essence by living fully in the present moment, offering a path to inner peace and lasting fulfillment.

How to Change by Katy Milkman

Combining cutting-edge behavioral science with practical advice, How to Change offers a clear roadmap for overcoming obstacles and making meaningful changes. Engaging stories and actionable strategies help readers understand the science behind their habits and provide tools for achieving lasting transformation.

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I hope these books help you reconnect with yourself, your faith, and others during this High Holiday season. If you have book recommendations to add to the list, please comment below or send them in a reply to this email.

Have a great week, and keep reading,

Arty

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What did you read over Shabbos?

A selection of shared Shabbos reads