#19: Elul I - Why Do We Keep Making the Same Mistakes? - With Rabbi Zimmerman

Every Elul, we promise ourselves that this year will be different. We’ll change, improve and leave old habits behind. So why do we so often find ourselves back in exactly the same place? In the first of this special Elul series, Mena Reisner sits down with Rabbi S. F. Zimmerman to explore what Elul and teshuvah are actually asking of us. Is Elul meant to be a time of fear or closeness? What does genuine teshuvah look like? Why is lasting change so difficult? And if we keep repeating the same mistakes year after year, does that mean our previous teshuvah failed? A practical and thought-provoking conversation about growth, failure and what Hashem really expects from us as we approach the Yamim Noraim. Elul opportunity: Join Vayidom’s 5-minutes-a-day Shmiras Halashon cycle and submit a name for Rabbi Zimmerman’s special tefillah at the Chofetz Chaim’s kever on his yahrzeit www.vayidom.com Time stamps: [00:00:00] – Intro & Elul Questions [00:01:55] – Elul: Melech Basadeh or Din? [00:06:40] – Elul as 30-Day Court Summons [00:12:10] – Avodah of Elul: Honest Self-Investigation [00:17:07] – Getting “Busy” in Ruchniyus: Help or Distraction? [00:21:36] – What Teshuva Really Is (Return vs Repentance) [00:26:57] – Teshuva Me’Ahava, Me’Yirah & How It Changes Sins [00:29:19] – Why We Repeat the Same Sins Every Year [00:36:36] – Is Repeated Teshuva Still Accepted? [00:45:00] – Jewish Teshuva & Turning in the Right Direction