Chai on Life

Today, I’m speaking with Tova Citrin. Tova is an author, songwriter, and AI technology executive who believes stories have the power to transform lives.

Born in the United States and now living in Israel, she draws inspiration from spirituality, Jewish mysticism, and the enduring resilience of the human spirit. Her work explores the places where faith, mystery, and destiny intersect.

After a serious illness in her late twenties set her on a deep personal and spiritual journey, she began writing what would become her debut novel, Ten Seconds to Midnight. The manuscript sat on a shelf for many years until she finally released it into the world in 2026.

When she’s not writing fiction, Tova works in artificial intelligence and trust & safety. She also creates original music as Aviya Sage, exploring themes of healing, purpose, and transformation.

My conversation with Tova just flowed. We covered sooo many things both about work and life. Speaking with Tova reminded me just how much is possible in this life we’re living and how it’s never too late to take on a dream you might have.

In this episode, we speak about:
-The breadth of the work she puts out into the world — both in a formal job and creatively

-How a serious illness changed the entire course of her life and led her on a religious journey

-What it was like living in Israel through October 7th, the war that followed and all that Israelis continue to face today

-How she creates a mindful space for herself amidst all of the stress

-What it was like going through a divorce in the middle of the war and losing her job simultaneously

-What inspired her to finally put her book into the world and how she utilized AI to get the book to its final stages

-Her advice for taking on your own passion project

…and SO much more. Tova is such a light, so authentic and inspiring and I can’t wait for you to learn from her. So now, without further ado, let’s get into the episode.

For more from Tova or to get in touch, visit tovacitrin.com.

Today, I’m speaking with Rebbetzin Dena Schusterman. Dena is a Chabad Shlucha, mother of 8, preschool founder, and decades-long community builder in Atlanta. 

Her new memoir, Stories Carry, goes deep into the stories we inherit across generations, the ones we carry forward and the ones we quietly rewrite from the inside. It’s not about dramatic exits, just the harder, slower work of becoming yourself within something you love.

This interview with Dena is real. In her book, she gives readers an inside look into a life that not many get to see. What may seem picture-perfect on the outside gets the human treatment. We hear the thoughts and feel the emotions going on throughout her life, both as a child in a Chabad family and then later, as a Rebbetzin leading a community of her own. In our conversation, we speak about:

-Why she wanted to write a memoir like this

-What it was like growing up as a child in a Chabad family that did so much outreach

-What her relationship with Shabbos is like now and the work it took to get her there

-What the thought process was behind expanding her family — if she ever felt pressure to have more kids and how she decided whether or not to keep growing

-What surrender looks like and really means in her relationship with Hashem

-Why she often feels different from other women in Chabad outreach

-What it was like for her father to leave shluchos

…and so much more.

For more from Dena, visit denashusterman.com.

Get her book here.

Today, I’m speaking with Relationship Expert, Chana Levitan. 

Chana is an educator, speaker and marriage therapist with more than 30 years of experience. She has lectured extensively across the globe and has counseled thousands of men and women on dating and marriage. She is the best-selling author of the books That’s Why I Married You and I Only Want to Get Married Once. 

This episode is a long time coming. I met Chana 14 years ago when I went to learn at Neve Yerushalayim for the first time and like so many others, became glued to her advice on relationships and what creates a lasting marriage. I read her first book before meeting my husband and read her second book on marriage after. Now, she has a third book out called Are We There Yet? The Road Trip to a Great Marriage which takes her knowledge on couples and relationships to the next level. 

In the book, she lets the reader in on the stories of 18 real-life couples. She details the challenges they had, misunderstandings and detours they went through and then how they got back to each other — strengthening their connections, communicating more effectively and building relationships that consistently grow deeper. She talks about her number one top tip for creating a strong, loving marriage and the advice you need on how to get there. It is a must-read and a good one to keep on the shelf to keep coming back to.

In our conversation, we speak about:

-Why she decided to write a second book on marriage

-Why more than half of a couple’s issues are actually not resolvable and what to do about it

-Her number one secret to creating a loving marriage that lasts

-What healthy disagreement looks like in a relationship

-What enduring love looks like

…and so much more!

To learn more from Chana and to get in touch, you can visit chanalevitan.com.

Hi everyone! Welcome back to another episode of The Chai on Life Podcast. I'm Alex Segal and today, I'm speaking with Keshet Starr, CEO of Shalom Task Force.

Keshet Starr, Esq. is an attorney, advocate, writer, and nonprofit leader dedicated to building safer, healthier Jewish communities. As CEO of Shalom Task Force—and previously CEO of the Organization for the Resolution of Agunot—Keshet has spent more than a decade addressing some of the Jewish community’s most complex and sensitive challenges, including domestic abuse and Jewish divorce denial. Known for bringing together legal expertise, communal understanding, and practical solutions, Keshet writes and speaks internationally about abuse, advocacy, Jewish law, and creating meaningful communal change. 

In this interview, we're peeling back the curtain on Keshet's life both in and out of the office.

In our conversation, we speak about:
-How she was able to become a CEO at such a young age

-How she dealt with imposter syndrome and making big decisions that didn’t always work out

-Her opinion on whether social media campaigns are helping the agunot cause

-What we can do at home to help the agunot cause, when it’s easy to feel so helpless

-How she is redefining what motherhood looks like in her life

-How she is redefining what parenthood can look like in the workplace

-What a day in her life looks like

-Some big decisions and shifts she made at home and with her husband to create a unique dynamic that works for everyone

-Her top time management tips

…and so much more!

This episode is such a great one to kick off the month of Cheshvan with. The holidays are behind us and now, we have routine back. This conversation will help you make the most of it.

This episode originally aired on 9/16/24 but is just as relevant today. Enjoy this replay as we get ready for Yom Kippur.

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Today, I am speaking with Yaffa Moskowitz, the Director of Education at ⁠Midreshet Rachel V’Chaya⁠, a seminary in Jerusalem. 

Here’s a little more about Yaffa: She is a native member the Far Rockaway community and was active in that community and the Five Towns for many years. Yaffa, her husband Danny, and seven children made aliya in the summer of 2013 and now live in Mitzpe Yericho. Yaffa served as teacher and Director of Ateres Seminary for women on the Queens College Campus for 13 years and she was also involved in the Neshei Shor Yoshuv community where she gave chaburas for married women.

I met Yaffa when I was a student exactly seven years ago at Midreshet Rachel and have continued to learn from her and with her since. She has such a wealth of knowledge and this conversation really turned into the perfect thing to listen to right in the middle of Elul preparing for the chagim.

During this time at Midreshet Rachel, the students learn from the sefer, Tomer Devorah, which teaches us about Hashem’s 13 Attributes of Mercy. As we learn about Hashem and understand who He is more, so to speak, we learn how we can emulate Him more in our own lives, and we used that text as the jumping off point for our conversation. 

As we spoke, we explored:

-What a “sin” actually is in Judaism (it may not be what you think) and how we can always get back on track

-How to separate ourselves from the sin and retain our confidence and closeness to G-d through the process

-How we can get to the core of what emunah really is on the most basic level and use these foundational concepts to connect to Hashem more deeply

-The restraint Hashem has with us every day and how we can apply that concept to our own lives and actions

-How to work on letting go of control

-Why we should speak to ourselves with more compassion from a Torah perspective

-When fear is appropriate in Judaism and what kind of fear that actually is talking about

-How we can continue to grow and elevate ourselves year after year

…and SO MUCH MORE!

To learn more about Midreshet Rachel V'Chaya, click ⁠here⁠.

Today, I’m speaking with Hadassah Eventsur.

Hadassah is an occupational therapist, educator, transformational coach, Mishpacha Magazine contributor, speaker, and the founder and CEO of MindfullyYou, an educational and support platform dedicated to helping neurodivergent individuals better understand their brains and build lives that work with—not against—them.

In her program, she helps women who feel overwhelmed by daily chores and responsibilities, those who are struggling time management and organization and others who simply want more peace, structure and confidence in their daily lives.

While she targets her work toward those who struggle with executive functioning skills, there are tips and strategies both in her course and in this episode that can help anyone.

This episode is like a giant deep breath. It will remind you to actually examine what you can handle and dial it back vs getting caught up in the just one more thing mindset or the feeling of needing to try every new recipe or that fancy one that looks super impressive. 

If you want to sign up for the Mindfully You program that is starting after Sukkos, (on Monday, October 5) you can register here.

To reach out to Hadassah personally, you can email her at [email protected].

Today, I’m speaking with Torah educator, Goldie Sion. Goldie was born in Caracas, Venezuela, and raised in Hollywood, Florida. She has worked with organizations in the past that include Olami Manhattan, Aish Aspire, Jam Israel and now works for Olami Souled. She is passionate about teaching Torah, giving shiurim, and inspiring others through creativity and connection with her Instagram: @goldiesjournal.

If you want to be feel connected and are on Instagram, I highly recommend you checking it out. Goldie’s words truly enter the soul. She has a way of making a connection to Hashem feel effortless, even though she acknowledges that it takes work. 

Our conversation is basically like one big emunah injection which is perfect as we’re about to enter the final week of Elul leading up to Rosh Hashanah.

In our conversation, Goldie speaks so eloquently about:

-How she brings Hashem into her day to day life from the big moments to the mundane

-How she elevates basic actions that make up her life

-What to do when you’re going through a difficult time or having trouble feeling connected to Hashem

-How to reframe your mindset when the answer you keep hearing is “no”

-What prayer can look like when you’re completely overwhelmed

-What the healthiest form of growth looks like

-How prayer really changes our lives

...and so much more!

If there is someone you want to see on The Chai on Life Podcast, email me at [email protected] or send me a DM @chaionlifemag. Thanks again, see you next week!

Today, I’m speaking with Sara Eisemann. Sara is a licensed clinical therapist and educator based in Oak Park, Michigan.

Sara currently serves as Co-Director of Education for Core's Mashpia Mentor Counselor (MMC) Training Program—a rigorous two-and-a-half-year initiative that equips women to provide Torah-based spiritual mentorship and emotional support within their communities. In addition to her clinical work, Sara is a certified dating coach. She is a regular contributor to Family First and she hosted the MakeShift podcast.

Today, Sara is speaking about the concept of “shalom,” or finding peace within all of the parts that make up who you are. In her clinical work, she’s come to see it as the thread that goes through so many different issues that come up with her clients.

As we move through Elul and gear up for the chagim, it’s a transformational framework to keep in mind. In the episode she uses this mindset to speak about:

-What shalom looks like within a family, community and within yourself

-How this helps a recovering perfectionist move away from unrealistic standards

-How we can make space for the “and” in life — the things that bring us joy and challenge at the same time, or the parts of ourselves that we both like and struggle with, for example

-Letting our authentic selves come through and getting rid of the “shoulds” that come up in any scenario 

-How we can avoid getting caught up in the worry about what others think of us and put more emphasis on what we think of ourselves

-The power of this work and how it’s designed to help you stay in the healthy headspace it creates

…and so much more!

While this topic may feel esoteric or lofty on the surface, it is filled with practical steps and shifts that you can make as soon as you turn off the episode. As we move through Elul and this period of self-reflection, it will help unlock that version of yourself you are striving for — or honestly, just let her come through.

Today, I’m speaking with educator and author Ilana Cowland. Ilana is the perfect person to kick off our Elul series with — she has spoken around the world, bringing warmth, humor and hard-won insight into the topics of love, intimacy, authentic connection and more.

She has seminars for couples that are known for being fast-moving, practical and genuinely fun. Her teaching is grounded in real life — she and her husband, Jamie have six children and now, grandchildren and the joys and challenges of building a family are woven into everything she shares. She is the author of the book, The Moderately Anxious Everybody and has a new book coming out which we touch on about raising children in a materialistic world.

I was so excited to speak to Ilana. She has been a speaker I have respected and looked up to for years now, and have heard her name so many times on my own Jewish journey. She has so much to share and she’s really someone I could have kept talking to forever about honestly any topic related to a woman’s life. 

In this episode, we try to go through as much as possible to get you to and through the upcoming chagim in the most connected way. We speak about:

-How she got into teaching and doing the work she’s doing today

-Anxiety and how it’s plaguing so many of us— we speak about the relationship between emunah and anxiety, how to diminish anxiety, what may be causing it and more

-How we can feel comfort in knowing Hashem is running the world instead of fear of what could happen as a result

-How to reframe what Rosh Hashanah is really about — I love Ilana’s approach here and thinking about it will completely change how you go into the holiday

-What prioritization really looks like when it comes to our relationship with Hashem, in motherhood, in marriage and more and how it changes as we move through life stages

-How we can find value in who we are in a world that is constantly throwing different messages toward us

-The power in slowing down

…and so much more!

Today, I’m speaking with ⁠Fally Klein⁠ — a teacher, facilitator and founder of Azamra Breathwork. Her work helps participants access the wisdom of the body, breath and soul, returning to the truth already held within.

Fally has an incredible story. Like the last episode, there was so much to fit in, we ended up going even longer than I usually do and I promise you it is worth the listen. Every minute is so rich - I was hanging onto her every word.

Fally has already lived through so many things — more than some go through in an entire lifetime. Some of which — like battling cancer — she speaks about in the episode and some of which she is preferring to keep private right now. When you listen to how eloquent she is, how much depth she brings to her journey and challenges, you will be blown away and if you’re like me, only want more from her.

In the episode, we speak about:

-Her battle with cancer as a teenager and what that experience taught her

-Her perspective on closure in life

-What real healing feels like

-How she worked to figure out her career and mission throughout her challenges and how that continues to evolve today

-How her connection with Hashem has deepened through her journey

-The power of breath work and how our breathing mimics the spiritual realm

-Two breathing techniques that can help you find more calm right now

…and SO MUCH MORE.

Get more from Fally on her website ⁠fallyklein.com⁠.

Get her book, Miracle Ride, ⁠here⁠.