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In honor of Elul and Rosh Hashanah, we’re re-releasing one of the most cherished conversations ever recorded on From the Inside Out Podcast, our 2019 interview with Rabbi Lord Jonathan Sacks זצ״ל. This was not only one of our very first episodes, it was also Rabbi Sacks' final recorded interview before his passing.

[Watch the extended video podcast here: https://youtu.be/QO9LPKJvnYU] 

What began as a conversation about Jewish identity, morality, and mentorship, became a masterclass in faith, leadership, and the quiet power of humility. From the Rebbe’s influence to his love story with Elaine, from confronting self-doubt to transforming the “I” generation into a “we” — this episode is packed with spiritual insight and deeply personal reflections.

Whether you're hearing it for the first time or returning for another listen, may Rabbi Sacks’ timeless wisdom inspire you in this season of renewal.

Topics include:

• How the Rebbe changed Rabbi Sacks’ life
• The hidden strengths of self-doubt
• The surprising power of WhatsApp over the pulpit
• Elaine Sacks’ role in shaping Rabbi Sacks’ leadership
• The shift from an “I” to “we” society
• Why the question “Why do bad things happen to good people?” has no answer
• Elul as a time of clearing space, not piling on resolutions
• How spiritual gifts increase when shared

🕊 May his memory continue to be a blessing.

GUEST BIO

Rabbi Lord Jonathan Sacks (1948–2020) was a global religious leader, philosopher, theologian, and moral voice of our time. He served as Chief Rabbi of the United Hebrew Congregations of the Commonwealth for 22 years and was a member of the UK House of Lords. A prolific author of nearly 40 books, he received the prestigious Templeton and Jerusalem Prizes for his contributions to faith and ethics.

He was a beloved teacher and lecturer at institutions around the world, including Yeshiva University, NYU, and King’s College London. Rabbi Sacks’ legacy continues through his writings, teachings, and the work of the Rabbi Sacks Legacy Trust.

He is remembered for his unwavering faith, humility, intellect, and his ability to uplift others through both reason and soul. His memory continues to inspire generations.

CHAPTERS

00:00 – Introduction  

05:10 – The Rebbe Changed His Life  

12:40 – The Gift of Self-Doubt  

19:25 – The Question That Went Viral  

25:00 – Behind Every Great Man…  

30:55 – From “I” to “We”  

37:15 – Why Giving Makes You Richer  

43:00 – Stories That Build Bridges  

48:15 – When Self-Help Isn’t Enough  

54:10 – The Truth About Creativity  

59:20 – “No Son of Mine Will Be Ashamed”  

1:04:45 – A Rosh Hashanah Wake-Up Call  

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