18Forty Podcast

Latest Episodes:

Gayle Kirschenbaum: Learning to Forgive My Mother [Teshuva 4/6] Sep 16, 2025

Show notes

This series is sponsored by Mira and Daniel Stokar.
In this episode of the 18Forty Podcast, we speak with Gayle Kirschenbaum—author of Bullied to Besties: A Daughter’s Journey to Forgiveness—about how she repaired her fraught relationship with her mother.
At the end of the podcast, we hear from her mother, Millie, herself, now over 101 years old. In this episode we discuss:

What does a “forgiveness coach” teach her students?
How can we repair relationships across generations?
What does it take to try to understand the full humanity of our parents?

Tune in to hear a conversation about healing, forgiveness, and teshuva through love.
Interview begins at 14:29.Gayle Kirschenbaum is an Emmy-winning TV producer, writer, photographer, coach, and speaker. She was invited to give a TED Talk called "No More Drama With Mama," about forgiveness and transforming difficult relationships into healthy ones.
References:
Top 5 by David Bashevkin
Bullied to Besties: A Daughter’s Journey to Forgiveness by Gayle Kirschenbaum
“No More Drama With Mama” by Gayle Kirschenbaum“
Cut! She's Chewing the Scenery; A Shih Tzu and Her Stage Mother Strive for Stardom”
The Godfather Part III
My Nose
The Nanny
You Can Heal Your Life by Louise Hay
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Sarah Hurwitz: Reclaiming Judaism from Shame and Blame [Teshuva 3/6] Sep 09, 2025

Show notes

This series is sponsored by Mira and Daniel Stokar.
In this episode of the 18Forty Podcast, we speak with writer Sarah Hurwitz—author of the new book As a Jew: Reclaiming Our Story from Those Who Blame, Shame, and Try to Erase Us—about what it means to be a “knowing Jew.”
In a time when we often feel compelled to justify our Judaism to the world, being Jewishly educated is no longer a luxury but a necessity. In this episode we discuss:

What does a proud Jew professionally associated with the Democratic Party make of the state of contemporary politics?
Where should one begin in trying to be an educated and involved Jew with a strong Jewish home?
How can the mussar literature be a great starting point to people looking to deepen their practice?

Tune in to hear a conversation about claiming for ourselves the tradition that so many try to take from us.
Interview begins at 11:14.
Sarah Hurwitz served as a White House speechwriter from 2009 to 2017, first as a senior speechwriter for President Barack Obama and then as head speechwriter for First Lady Michelle Obama. She is the author of Here All Along: Finding Meaning, Spirituality, and a Deeper Connection to Life – in Judaism (After Finally Choosing to Look There) and As A Jew: Reclaiming Our Story From Those Who Blame, Shame, and Try To Erase Us.
References:
As a Jew: Reclaiming Our Story from Those Who Blame, Shame, and Try to Erase Us by Sarah Hurwitz
Here All Along: Finding Meaning, Spirituality, and a Deeper Connection to Life – in Judaism (After Finally Choosing to Look There) by Sarah Hurwitz
The Mighty Ducks
Everyday Holiness: The Jewish Spiritual Path of Mussar by Alan Morinis
Mesillat Yesharim by Moses Chaim Luzzatto
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DovBer Pinson: The Jewish People's Path of Teshuva [Teshuva 2/6] Sep 03, 2025

Show notes

This series is sponsored by Mira and Daniel Stokar.
In this episode of the 18Forty Podcast, we speak with Rabbi DovBer Pinson—a scholar, author, teacher, and spiritual mentor—about how we can rethink teshuva in light of the challenges we face today.
In this episode we discuss:

What is the difference between “lower” and “higher” teshuva?
How should the Jewish world recalibrate in the face of the recent rise in antisemitism?
How can we learn to be better at loving the Jewish People, including the Jews with whom we have severe disagreements?

Tune in to hear a conversation about what it means to return to our eternality in a rapidly changing world.
Interview begins at 8:40.
Rav DovBer Pinson is a world-renowned rabbi, scholar, author, teacher, and spiritual mentor. Through his books, lectures, and seminars he has touched and inspired the lives of thousands the world over. Rav Pinson is the Rosh Kolel of the IYYUN Yeshiva/Kolel, Marah D'asra of 84 Viola, and heads The IYYUN/CHABAD Center in Brownstone Brooklyn, New York.
Topics (Produced by Sofer.AI):
Podcast introduction and theme — 0:14
Meeting Rav DovBer Pinson and his impact — 3:51
Life as a text: looking for confluence — 7:00
Introducing the discussion on teshuva — 8:42
Lower vs. higher levels of teshuva — 10:27
Diaspora, Israel connection, and shifting Jewish identity — 12:34
Specific focus of teshuva for the Orthodox Jew — 16:00
Modern identity collapse and reclaiming self — 17:29
Agency and free choice in Judaism — 19:20
Five dimensions of reality in Sefer Yetzirah — 20:23
Orthodox world lagging by fifty years — 22:25
Time vs. space: Mishnah acronym insight — 23:57
Worries about Orthodox commitment and packaging — 26:05
Yeshiva world as a train without an engine — 28:59
Subconscious communication across Jewish communities — 30:29
Peripheral origins vs. established Hasidic families — 31:49
Understanding the relationship with the Land of Israel — 32:51
Israel as a nation vs. a people — 34:05
Collective awareness of shared destiny — 36:16
Yeshiva League analogy and need for new language — 37:31
Taking personal responsibility for all Israel — 41:36
Tension between love for Jews and love for humanity — 43:03
Unity of Torah, God, and Israel — 45:48
Yeshiva learning without a structured curriculum — 47:37
Rebbe’s vision: every Jew as a shaliach — 49:43
Mission of Judaism beyond meritocracy — 54:22
Hope expressed in the daily prayer — 57:17
Jewish calendar holds a Guinness record — 59:08
Personal struggle with criticism over gay Jews — 60:13
Pain from establishment and public backlash — 61:21
Seeking trusted guidance to navigate criticism — 65:53
Personal teshuva: reconciling with critics — 68:53
Humility as source of creative innovation — 71:06
Current crisis as catalyst for collective change — 73:11
The Torah of the moment: Messiah and presence — 74:50
Books that pose good questions — 75:51
Future vision: every day becomes a holiday — 77:48
Great-grandfather lineage in Chabad scholarship — 80:00
Balancing Talmudic study with Chassidic heart — 81:43
Fascination with French Jewry of the 12th century — 82:54
Personal sleep schedule post-COVID — 84:16
Facing personal criticism and baggage — 90:11
Uniting through the Jewish community — 92:27
References:
18Forty Podcast: “Haym Soloveitchik: How Modernity Changed Our Relationship to God”
18Forty Podcast: “Zohar Atkins: Between Philosophy and Torah”
Zohar
Tanya Chapter 32
Aleinu
For more 18Forty:
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Rochi Ebner: Rav Kook's Return to Our Soul [Teshuva 1/6] Aug 26, 2025

Show notes

This series is sponsored by Mira and Daniel Stokar.
In this episode of the 18Forty Podcast, we speak with Rachel Tova Ebner, translator of a new volume of the teachings of Rav Kook, about what the spirituality of Rav Kook adds to our Jewish practice and to our understanding of ourselves.
As we approach Rav Kook’s yahrzeit (3 Elul), we’re directing our attention to the spiritual dimension of Yiddishkeit outlined in his works. In this episode we discuss:

What does Rav Kook teach us about our yearning for God?
What is the role of feelings in our inner work?
What does it mean for us to change as the Torah stays the same?

Tune in to hear a conversation about the paradox inherent in trying to “change the past” via teshuva.
Interview begins at 14:57.
Rachel Tova Ebner grew up in Manhattan and made Aliyah to Jerusalem with her family in 1982. She is linguist and lyricist, a teacher and translator, with a Master’s degree in Hebrew from the Bernhard Revel Graduate School of Yeshiva University. Her most recent professional endeavor was to participate in the translation of the new Koren Tanach. She has three children and eleven grandchildren.
Chapters (Produced by Sofer.AI):
Teshuvah 0:14
Re‑examining Our Bullseye: The Conceptzia Idea 3:38
Lakewood Yeshiva’s Future and Community Burnout 6:50
Generational Mission Shifts and Klal Yisrael 8:37
Introducing Rav Kook’s Torah of Tomorrow 11:52
Translator Rachel Tova Ebner on Her Father’s Influence 15:00
Early Memories of Learning with Rabbi Bernstein 16:15
Limits on Naming and Speaking About God 21:32
The Classic Child’s Question: Is God in the Toilet? 22:46
Ikveta d'Mishicha: The Era of Messianic Footsteps 25:18
Rav Kook’s Call for New Spiritual Consciousness 26:18
Direct Encounter with God—Beyond Rabbis and Texts 28:01
Rav Kook’s Historical Context and Practical Inner Work 43:28
Compassion and Inner Work with the Soul 45:36
Rav Kook on Teshuva and Cosmic Will 47:30
Personal Metaforms: Smoking as Spiritual Symbol 50:32
Rav Kook’s Vision for Secular Israelis 52:32
Calling Artists of the Sacred in Modern Times 55:00
The Summons to Holy Consciousness Excerpt 57:01
Choosing a Rav Kook Translation for Study 62:23
Evolution as Cosmic Optimism in Rav Kook 64:13
Finding a Spiritual Path Beyond Halacha 67:08
Critique of Galut and Return to Eretz Yisrael 68:17
Personal Sleep Habits: A Goyish Schedule 70:06
Rav Kook’s Vision: Renewing the Old, Sanctifying the New 73:27
Intuition and Faith in Personal Spiritual Direction 75:09
Despair as Catalyst for Renewal in Orot Hateshuva 76:56
Closing Remarks and Sponsor Acknowledgments 80:49
Traditional Closing Prayer and Song 81:50
References:
18Forty Podcast: “Rav Judah Mischel: A Change in Progress”
The Torah of Tomorrow: OneSong by Rachel Tova Ebner
Renewing the Old, Sanctifying the New: The Unique Vision of Rav Kook by Marc B. Shapiro
18Forty Podcast: “Marc B. Shapiro: Where Does Orthodox Judaism Come From?”
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Joey Rosenfeld: What Does Jewish Mysticism Say About This Moment? [Teshuva Bonus Episode] Aug 19, 2025

Show notes

This series is sponsored by Mira and Daniel Stokar.
In this episode of the 18Forty Podcast, we speak with rabbi, psychotherapist, and “translator” Joey Rosenfeld about how our generation can understand languages of mysticism, philosophy, and suffering in today’s chaotic world.
In this episode we discuss:

Where should we channel our spiritual work as we near two years since October 7?
Will Mashiach come in our lifetime?
What is the purpose of yearning and desire?

Tune in to hear a conversation about how “Yiddishkeit is the guardian of deficiency.”
Interview begins at 8:49.
Rabbi Joey Rosenfeld is a practicing psychotherapist in the addiction field focusing on the interface between philosophy, spirituality, and psychology. His shiurim on Jewish philosophy, Kabbalah and the inner workings of the human soul have been watched and listened to by thousands around the world and he has a dedicated following of students from the entire spectrum of the Jewish community.
References:
Tikkunei Zohar
“The Source Of Faith Is Faith Itself” by Aharon Lichtenstein
Pirkei Avot 4:2
Halakhic Man by Rabbi Joseph B. Soloveitchik
Tanya ch. 36“
Why Is There Something, Rather Than Nothing?” by Sean Carroll
Mishneh Torah by Maimonides
Sippurei Maasiyot by Rebbe Nachman of Breslov
“Anthem” by Leonard Cohen
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David Bashevkin: My Dating Story [Re-Release] Aug 12, 2025

Show notes

This episode was sponsored by Jerry and Esther Williams in honor of 18Forty and Shalom Task Force.
While we wait for the next new episode of the 18Forty Podcast, we revisit Dovid Bashevkin's 2022 deep dive into the world of dating. As we explore the realm of relationships, Dovid uses his own journey to help us find the proper framework for balancing one’s romantic, religious, and professional identities.

How can one stay connected to their religious self while simultaneously evolving?
What’s Dovid’s best advice for dating and marriage?
Why are we afraid to commit to no?
How can we ensure that the years ahead are the best years yet?

Tune in to hear a conversation on love, commitment, and commitment to commitment.
References:
Shalom Task Force The Orchard: A Novel by David Hopen
Tehillim 27:10“
Evolving Religiously During Singlehood” on Singled Out Podcast by Zahava Moskowitz
Bambi
Garden State
Dovid Bashevkin on Twitter
“Spending the Seder Alone” by Dovid Bashevkin
Solitude, A Philosophical Encounter by Philip Koch
Cast Away 18Forty – “Rav Moshe Weinberger: Can Mysticism Become A Community?”
“Bashert: My One and Only?” on YUConnects CandiDate Podcast
“The Paradox of Choice” by Barry Schwartz
“The Howard Stern Show: Actor And Comedian Aziz Ansari Visits The Show”
“Signed, Sealed, Delivered” by Dovid Bashevkin
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How Jews Date in the Modern World (Re-Release) Aug 05, 2025

Show notes

As the 15th of Av approaches, we are returning to this episode on how different Jewish communities date to honor the Jewish "holiday of love."
This episode is sponsored by Anonymous who is fond of Shalom Task Force & 18Forty.
On this episode of 18Forty, we explore the world of Jewish dating. We spoke to insiders and experts from the Chassidic community, “Yeshiva Orthodox” community, and Modern Orthodox community, looking at the commonalities and differences between each community’s approach to finding and building loving relationships. Each community emphasizes different dynamics and difficulties of the process of dating, and by considering them together and independently we can gain a greater understanding of the pressure points around love. How a community approaches dating is a test case for so many of a community’s values and vulnerabilities. In this episode, you’ll hear from representatives of each community that are intimately involved with the project of communal norms around dating, and be asked to think about your own assumptions and hopes for love. In this interview, we discussed:

How does each Jewish community approach dating, from shadchans to dating apps and everything in between?
What does a community’s approach to dating tell us about the Jewish approaches to love and commitment?
What can we learn from the dating practices of communities that are different from our own?

Interviews start at 10:31
Dr. Yosef Sokol, one of our representatives from the yeshiva world, is a psychologist and the lead researcher of the recent study on the data behind the “shidduch crisis.” We also speak with Dr. Isaac Schechter, another author of the study, Dr. Efrat Sobolofsky, director of the YUConnects matchmaking-and-education program, and Dr. Devorah Mansdorf Agami, an endodontist who met her husband on JSwipe.
References:
Rabbi Mordechai Lightstone
“Examining Average Age at First Marriage within Orthodox Judaism: A Large Community-Based Study” by Yosef Sokol, Naomi Rosenbach, Chayim Rosensweig, Chynna Levin, Shifra Hubner, and Isaac Schechter
Bikur Cholim of Rockland County ARRC Institute
YUConnects
JSwipe
Dovid Bashevkin on YUConnects CandiDate
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Hadas Hershkovitz: On Loss: A Husband, Father, Soldier [Loss 3/3] Jul 29, 2025

Show notes

In this episode of the 18Forty Podcast, we speak with Hadas Hershkovitz, whose husband, Yossi, was killed while serving on reserve duty in Gaza in 2023—about the Jewish People's loss of this beloved spouse, father, high-school principal, and soldier.
In the second year of the war, we’re grappling not only with the depth of our losses, but with how to make meaning of them as we continue to live in their aftermath. In this episode, we discuss:

How has the loss of Hadas’s husband sparked a renewed urgency in her dedication to uplifting the Jewish People?
How do we confront the anger and blame we may feel toward others in the wake of collective tragedy?
How can we cultivate the positive thoughts and spiritual clarity needed to uphold our moral responsibilities in difficult times?

Tune in for a heartfelt conversation on what it means to transform Torah into a living song sung by the Jewish People.
Interview begins at 30:30
References:
Psalms 23
Hasidic Tales of the Holocaust by Yaffa Eliach
Seinfeld: “The Bottle Deposit”
“יש כאן יותר מזה" by Hanan Ben Ari
Deuteronomy 31
Arukh HaShulchan by Yechiel Michel Epstein
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Elissa Felder & Sonia Hoffman: How the Jewish Burial Society Cares for the Dead [Loss 2/3] Jul 22, 2025

Show notes

In this episode of the 18Forty Podcast, we talk to author Elissa Felder and her daughter Sonia Hoffman—both of whom have experienced the loss of a child and serve on a chevra kadisha—about what the Jewish burial society teaches us about confronting death. In this episode we discuss:

How does the process of purifying a dead body work—and how is it possible to purify a dead body at all?
What Kabbalistic practices are performed by chevra kadisha to bring dignity to the body and soul?
How can we “normalize” discussions about grief and death?

Tune in to hear a conversation about how care for the deceased is a “love story” between the Jewish People and God.
Interview begins at 15:31.
Elissa Felder started and actively manages Core’s community of practice for women who serve on a traditional chevrah kadisha. The knowledge she acquired through her work motivated her to write From One Life to the Next Life; The Sacred Passage after Death, a memoir about the loss of her baby son. She is the head of her local chevrah kadisha and speaks widely on this topic.
Sonia Hoffman is a Limmudei Kodesh teacher at Kohelet Yeshiva in Philadelphia. She is a daughter, mother, wife and member of the Bala Cynwyd community. She is also an active member of the Philadelphia Chevra Kadisha, having started during COVID to help with this mitzvah. After the loss of their daughter in 2016, she began speaking about her experience with loss and sharing resources with the community on ways in which we can move forward after tragedy. In addition, Sonia began hosting an annual event in her daughter's memory to bring awareness to the community around the topic of infant loss and relationship with God.
References:
Teshuvot HaRadbaz Volume 3, 985
Torat HaAdam, Introduction
“Passing Through” by David Bashevkin
Berakhot 10a
“Reconciling Opposites: Uncommon Connections in the Halakha of Mourning” by Emanuel Feldman
From One Life to the Next Life; The Sacred Passage after Death by Elissa Felder
The Wild Edge of Sorrow: Rituals of Renewal and the Sacred Work of Grief by Francis Weller
The Choice: Embrace the Possible by Dr. Edith Eva Eger
Consolation: The Spiritual Journey Beyond Grief by Maurice Lamm
Gesher Hachaim - The Bridge of Life by Rabbi Yechiel Michel Tucazinsky
Rabbi Yitzchak Hutner's Theology of Meaning by Alon Shalev
For more 18Forty:
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Shlomo Brody & Beth Popp: Demystifying Death and the End of Life [Loss 1/3] Jul 15, 2025

Show notes

In this episode of the 18Forty Podcast, we talk to Rabbi Shlomo Brody and Dr. Beth Popp, who work with Ematai, an organization focused on end-of-life care, about the process of death and how we ought to live with our own mortality.
In this episode we discuss:

How do we connect to eternity within this finite existence?
What halachic issues must we consider when making end-of-life decisions?
What happens to the body of someone who’s died?

Tune in to hear a conversation about how we can sanctify life in the face of mortality.
Interview begins at 18:30
Rabbi Dr. Shlomo Brody is the executive director of Ematai and a columnist for The Jerusalem Post. His first book, A Guide to the Complex: Contemporary Halakhic Debates, received a National Jewish Book Award. His newest book, Ethics of Our Fighters: A Jewish View on War and Morality, was published in 2023. A summa cum laude graduate of Harvard College, he received rabbinic ordination from the Israeli Chief Rabbinate, an MA in Jewish philosophy at the Hebrew University, and his PhD from Bar Ilan University Law School.
Dr. Beth Popp is a professor on the faculty of Icahn School of Medicine at Mount Sinai in New York, specializing in Hospice and Palliative Medicine. She has served on hospital ethics committees for most of her career and presents regularly to community groups to clarify the role of hospice and palliative care in the healthcare system. She has been extensively involved in educating rabbinic leaders about the medical aspects of serious illness and end-of-life care.
References:
Rabbi Yitzchak Hutner's Theology of Meaning by Alon Shalev
Pachad Yitzchak al Shavuot by Rabbi Yitzchak Hutner
“Letters of Love and Rebuke From Rav Yitzchok Hutner” by David Bashevkin
Halakhic Man by Rabbi Joseph B. Soloveitchik
Ethics of Our Fighters: A Jewish View on War and Morality by Rabbi Dr. Shlomo Brody
A Guide to the Complex: Contemporary Halakhic Debates by Rabbi Dr. Shlomo Brody
The Immortal Life of Henrietta Lacks by Rebecca Skloot
The Denial of Death by Ernest Becker
Seinfeld: “The Comeback”
Being Mortal by Atul Gawande
Kaddish by Leon Wieseltier
When Breath Becomes Air by Paul Kalanithi
For more 18Forty:
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