Simon Baum is a seasoned lawyer, a Daf Yomi maggid shiur (twice daily!), and a thoughtful voice on what it means to live an integrated Torah life while fully immersed in the workforce. But his real story begins not with success, but with a breakdown.

In this moving and practical conversation, Simon opens up about:

• Hitting rock bottom after closing a billion-dollar deal

• Reframing his relationship with Hashem from stress to serenity

• Giving a Daf Yomi shiur as a path to deeper learning and community

• The relationship between professional success and spiritual growth

Simon shares his high-powered legal career, his weekly flights between London and Israel, and the moment of inner collapse that made him question everything—even at the peak of outward success.

Real growth came not from switching jobs—but from changing his view of what it means to live with Hashem. Guilt-based Yiddishkeit gave way to an honest, intimate relationship with the Ribbono Shel Olam.

Simon moved to a Tel Aviv law firm, enabling a less frantic schedule and new consistency in his learning. His twice-daily Daf Yomi shiur has grown into a tight-knit chevra with shared values and simchas.

Work isn’t just a B’dieved. Simon explains how his law career actually deepened his Torah—offering insights, challenges, and identity shifts he couldn't have experienced elsewhere.

Simon explores how to grow spiritually without falling into toxic introspection, and how healthier self-worth leads to healthier avodah, relationships, and responses to stress.

• Olam HaYedidus by Rav Shlomo Wolbe

• Bikshu M’sham and K’savim by Rav Soloveitchik

• Crossing the Unknown Sea by David Whyte

Money Quote: “Real relationships have closeness and distance. You don’t do Avodas Hashem just to tick boxes—you do it because it’s real, and you want to live it.”

Chapters

00:00 Intro and Early Life

04:17 The Turning Point: Realizing the Need for Change

10:02 Transforming Life: Practical Changes and New Perspectives

17:00 Integrating Faith and Daily Life: A New Approach

21:59 The Pilgrimage of Identity in Work

23:50 Crisis and Self-Discovery

27:19 Managing Stress and Relationships

31:17 Navigating Self-Reflection and Growth

35:39 Seeking Professional Help vs. Self-Help

41:50 Future Aspirations

44:00 Lightning Round