Would you ever run a marathon without training for it? Would you ever head into a job interview without learning at least a little about the company? Would you ever go on a vacation and not pack anything? 

I pose these questions as answers to another question that I am often asked: What is the purpose of the High Holy Days, particularly Yom Kippur, which is called a “Shabbat Shabbaton, a Sabbath of Sabbaths” in the Torah? Why take off work and ignore other responsibilities to spend 25 hours taking stock of our lives and focusing on our wrongdoings and mistakes – and fast while we’re at it? Life is hard enough; why not deal with our slip-ups as they come up, resolve them, and move on?  

Out of an earnest desire to be diligent, we make frequent commitments to ourselves. How many of us decide that we will exercise each day? Or promise ourselves that we’ll work on that report over the course of a few months, only to find ourselves writing furiously over the course of a sleepless week? It’s the same problem with committing to a practice of self-reflection; it can be hard to follow through. 

One way to be sure to stick to a good habit is to have a buddy – someone who forces us to set aside time to take that jog or to meet in the library. Someone who relies on you to support them in the endeavor, just like you rely on them for the same thing. That’s what we do during this season of the High Holy Days: We are all part of the buddy system. While it’s hard to maintain an intense self-reflective practice all year round, we make sure that we set aside a time to do it together. 

When Jews gather on Yom Kippur, we ask ourselves questions that people often ask at the end of their lives. “What have I accomplished? What do I wish I had done differently? Do I have regrets about how I spent my time and my energy and my money? Have I fostered good relationships? Do I have love in my life?” Of course, what is different about Yom Kippur is that instead of holding those questions up as a final reflection on our lives and our actions, we get to move forward. The morning and afternoon of Yom Kippur are difficult – we are forced to retreat from the world for a whole day, forced to deny our bodies so that we can focus on the state of our souls, and come face to face with our deeds and our questions. But in the evening, and right after Yom Kippur, we break our fast, we emerge from our questioning and our doubt, and we are ready to re-enter the world with renewed spiritual strength.

The problem is, we don’t always have control over when we have to ask ourselves these difficult questions about the fragility of life, about what makes us feel safe in the world, about how we cope with disappointment and regret. Sadly, we often face these questions at moments where we least expect them, during times of tragedy. We are often in a state of shock when we need to face the realities that are most challenging, whether it is the upheaval that plagues our nation and our world, or whether it is the sadness and the pain that we experience in our personal lives. When we face crisis, we and the people we care about find ourselves facing these most heavy questions. But if you’ve never dealt with the questions that make up a spiritual life — questions about regret, relationships, and purpose — it’s hard to commence that process in a time of tragedy. 

This is the beauty and the logic of creating a season for our questions and for our reflections. Yom Kippur is a way for us to practice. We take time out of our days, a set time each year, in order to put our lives underneath the microscope, to think about our actions, our successes, our failures, our regrets, and to answer some of these questions. When we emerge from this process, we are better equipped to handle the challenges, and even the tragedies, that life throws our way. When we do face difficulties, we are not strangers to the questions that accompany them. We’ve practiced and trained and together we have discovered some of our answers, during the predictable, contained, and safe moments of Yom Kippur. It gives us the spiritual strength and training that we need to progress in the year to come, and the chance to train with the help of friends. 

But before we head into the holiday of Yom Kippur, we celebrate the Jewish New Year on Rosh Hashanah, where we kick off our season of reflection, introspection, and renewal. Whether you’re Jewish or not, I’d love for you to join The Downtown Jews for an inspiring Rosh Hashanah experience on September 29, 2019. You can find more information and registration details by clicking here.  


  • DEENA GOTTLIEB serves as the rabbinic fellow at the Jewish Community Project of Lower Manhattan, a vibrant, pluralistic community in Tribeca. In 2018 she founded The Downtown Jews, a group to help young professionals explore Jewish identity and create community. Deena graduated from Yale University in 2015 and is in her final year at Hebrew Union College in NYC.