73. Ayekah? Wisdom for the High Holidays (and Beyond): With Rabbi Simon Jacobson

From the Inside Out: With Rivkah Krinsky and Eda Schottenstein

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Episode Sponsor: Karen Hashana
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Episode Details:
Ready to uncover the profound wisdom of Rabbi Simon Jacobson on spiritual growth and the curious intertwining of guilt and religion? We're bringing you a soul-stirring conversation that fundamentally reframes how we perceive high holidays - as a time for accountability and nurturing a trusting relationship with God, rather than a time for guilt. Let's shatter the comfort zones together as we embrace new experiences and channel the untapped energy of Rosh Hashanah.
In the heart of our discussion, Rabbi Jacobson illuminates the delicate balance between asking Hashem for our desires and humbly surrendering to His divine plan. He shares invaluable insights into two fundamental steps in Judaism: Iskafya and Ishabhah, that teach us how to transform negative impulses into positive ones and resist indulgence. To top it all, we delve into the deeper meanings of Rosh Hashanah and Yom Kippur, revealing how to connect meaningfully with God during these sacred periods.
Wrapping up our enlightening journey, we explore the power of vulnerability, the potential for growth that lies in the disruption of comfort zones, and the true essence of Rosh Hashanah and Yom Kippur. Rabbi Jacobsen shares moving stories and lessons that will inspire you to live up to his teachings and fulfill your unique mission. So, join us in this thought-provoking episode and discover how you can bring Hashem's light into the world, one day at a time.
60 Days Spiritual Guide Link:
https://www.amazon.com/60-Days-Spiritual-Guide-Holidays/dp/1886587248
Website/Podcast Link:
https://www.chassidusapplied.com/

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1. Principles of Charity and Spiritual Growth (00:00:00)

2. Guilt-Free High Holidays (00:04:15)

3. Embracing Newness and Taking Initiative (00:11:07)

4. Balancing Prayers, Surrendering to God's Plan (00:21:50)

5. Preparing for Rosh Hashanah (00:29:34)

6. Rebuilding Relationship and Overcoming Trauma (00:41:36)

7. Meaningful Prayer, Overcoming Insecurity (00:47:34)

8. Power of Comfort Zone and Growth (00:56:56)

9. The Power of Faith and Resilience (01:07:38)

10. Essence of Rosh Hashanah and Yom Kippur (01:11:19)

11. Memorable Moments With the Rebbe (01:19:23)

12. Bringing the Rev's Teachings to Life (01:30:25)

13. Meaningful Conversations and Spiritual Rituals (01:38:06)

14. Exploring Joy and Security in Sukkot (01:44:08)

15. Heroes and Role Models (01:53:43)

16. Finding Inspiration and Learning From Mistakes (02:00:48)

17. Questioning Where You Stand (02:12:49)