Totally Booked with Zibby: Esther Chehebar, SISTERS OF FORTUNE

Air Date: September 5, 2025
Host: Zibby Owens
Guest: Esther Chehebar
Novel Discussed: Sisters of Fortune

Overview

In this episode, Zibby Owens welcomes debut novelist Esther Chehebar, author of Sisters of Fortune, to discuss her new book, the intricacies of the Syrian Jewish community in Brooklyn, and the author's personal journey from writing essays and blogging to publishing her first novel. The conversation explores themes of sisterhood, community, tradition, body image, and the creative process, all delivered with humor and candidness.

Key Discussion Points & Insights

Introducing Sisters of Fortune (04:44 – 05:25)

• Premise: The novel focuses on three young Syrian Jewish sisters in Brooklyn as they navigate dating, marriage, tradition, and modernity. The story is rooted in community and explores the tension between traditional and modern values.
  • Quote: "Sisters of Fortune is a sister story...about community and it's a story about traditionalism and modernism...what we as women ultimately want for ourselves and the different paths that we take to get there." — Esther (04:56)

The Humor and Observation of Family and Culture (05:25 – 06:02)

• Zibby praises Esther’s keen observation of family dynamics and humor, especially regarding the “mishigos” (craziness) of life in a tight-knit community.
  • Quote: "You are a keen observer of human behavior and families and all the sort of mishigos of life. Like, it's funny. It's really funny." — Zibby (05:25)
• Esther credits her upbringing among unintentionally funny people, which informs her approach.

Body Image, Dieting, and Food Culture (06:02 – 09:41)

• Zibby highlights a passage about weight and dieting, drawing personal parallels to her own Jewish upbringing.
  • Memorable Passage Read Aloud: "Each of us women, my sisters, my mother and I walk around the house pretending like we're the only one not on a diet.... My mother tells us we look good the way we are and then is the first one to compliment us when a quarter of a pound is lost." (06:02)
• Insight: Esther unpacks the tension between being part of a food-loving culture and the simultaneous preoccupation with body image, especially for women. She calls out both the pressure to eat and the pressure to conform to physical standards.
  • Quote: "Food is such a big deal and gathering around the table is such a big deal… you are expected to eat and enjoy… and then at the same time you are preoccupied with body weight because you're constantly comparing yourself.” — Esther (08:31)

Sibling Dynamics and Competition (10:14 – 13:40)

• Esther describes her real-life inspiration as the oldest of three sisters, explaining the natural competitiveness and desire to carve out unique identities.
  • “You have that innate desire to differentiate yourself from your sisters. But…when they're dating…they are competing with one another in this very small dating pool of eligible men.” — Esther (11:44)

The Syrian Jewish Community: Context and Distinctions (13:40 – 17:07)

• Esther gives a brief history of the Syrian Jewish community, its origins, customs, insularity, and continued vibrancy in Brooklyn.
  • “Our ancestors, way, way back, came from Spain…The Syrian community in Brooklyn is a huge and growing, very dynamic community whose descendants mainly come from Aleppo and Damascus…We mainly marry within the community.” — Esther (13:53)

Esther’s Path to Becoming a Novelist (17:07 – 20:11)

• Education and Early Career: Esther attended NYU (Gallatin), started as an environmental science major, wrote a blog as a young wife in NYC, and got her first writing job at Man Repeller.
• Graduate School: Got her MFA at The New School, initially wanted to write nonfiction but found her voice in fiction after being encouraged by a professor.
  • “I always wrote my whole life. I never thought that it would be a viable career path...But I always adored books, adored writing.” — Esther (17:35)

Writing, Motherhood, and Managing It All (20:11 – 20:49)

• Esther is a mother to three young children and describes the challenges and joys of balancing writing, parenting, and now book promotion.
  • “Stillness is when I start to feel like...And then, you know, it all happens all at once and it's fun. And it's fun for my kids to see too, you know.” — Esther (20:31)

Evolution of the Manuscript & the Value of Rejection (24:55 – 27:19)

• The book underwent multiple drafts: nonfiction, essays, then fiction with interwoven perspectives of all three sisters. Early rejection and editorial challenges ultimately led to a story that feels “complete.”
  • “I wasn't able to tell the stories that I wanted…in the nonfiction realm...Let me try my hands at fiction, and like, it just completely freed me up immediately.” — Esther (25:06)

Core Message of the Novel (27:19 – 30:09)

• Esther wants readers to see the complexity and joy of female, Jewish, and specifically Syrian Jewish experiences.
  • “I do want to celebrate what it means to be Jewish today. And specifically celebrate this community that has endured…with a lot of flavor and with a very, very interesting history.” — Esther (28:29)
• Emphasizes moving beyond just stories of adversity, aiming to show cultural richness and resilience.

What’s Next? The Next Novel! (30:09 – 32:13)

• Esther is drafting a new book about a group of forty-year-old women at a tennis retreat in Boca, tentatively titled "Love, Forty."
• Zibby remarks on the similarity to another upcoming title from her publishing house, leading to a humorous exchange.

Advice for Aspiring (Jewish) Authors (32:39 – 34:22)

• General Advice: Write (record something) every day, even small snippets.
• Jewish Authors: Don’t self-censor or tiptoe; embrace the tradition of boldness and honesty in Jewish storytelling.
  • “Don't tiptoe. I think that there's a Jewish tradition in art of diving into the deep end, and that's what makes Jewish creators and artists so influential, so dynamic…” — Esther (33:55)

Notable Quotes & Memorable Moments

• On Body Image and Food:
  “There was always this dichotomy between you're not eating enough, eat, eat, eat food... And then you get older…you're constantly comparing yourself to other women.” — Esther (07:22)
• On Rejection:
  “I'm actually thankful for that rejection and all of those different iterations because when I read the book now, it does feel complete to me. And I'm very proud of the story that I'm telling.” — Esther (26:40)
• On Jewish Joy vs. Adversity:
  “For me, it's really, really, really important to get back to the joyfulness of being Jewish.” — Esther (28:00)
• On Sisterhood:
  “You don't want to compare and you don't want to have resentment because...you have this overriding bond and love for one another. But outside factors do come into play.” — Esther (12:02)
• On Writing Advice:
  “Just write every day...It could be a note in your notes app. Just keep your eyes open and record something.” — Esther (32:46)

Timestamps for Key Segments

• Introductions and Overview: 04:16–04:44
• Book Premise and Inspiration: 04:44–05:25
• Family and Community Humor: 05:25–06:02
• Body Image and Diet Culture: 06:02–09:41
• Sibling Comparison and Competition: 10:14–13:40
• Explaining the Syrian Jewish Community: 13:40–17:07
• Path to Writing and Publication: 17:07–20:11
• Motherhood and Writing: 20:11–20:49
• Manuscript Drafting and Lessons Learned: 24:55–27:19
• Core Message and Legacy: 27:19–30:09
• Next Book Talk and Publishing Anecdotes: 30:09–32:13
• Advice to Writers: 32:39–34:22

Closing Thoughts

This episode is a heartfelt conversation between two writers who share a love of books, family, and joyful cultural storytelling. Esther Chehebar’s Sisters of Fortune offers a nuanced, affectionate, and witty depiction of the Syrian Jewish community and the interplay of tradition and modernity for women coming of age. Zibby’s probing questions and personal insights enrich the discussion, making this episode a must-listen for fans of contemporary fiction, cultural narratives, and anyone who appreciates the power of sisterhood and authentic storytelling.