Embracing the Bittersweet

This summer, I was incredibly privileged to spend two weeks at the Jewish Theological Seminary’s Davidson Graduate School of Jewish Education as a second-year fellow in the Day School Leadership Training Institute. This fellowship, made up of Heads of School and aspiring Heads from across the U.S. and Canada, has been a truly valuable experience to me, not just as a way to continue developing myself as a leader, but also because it is an ongoing opportunity to share the successes (and challenges!) with colleagues, mentors, and other leaders and stakeholders in the greater field of Jewish Education. Through my participation, Ezra and its school leadership, as well as the Board of Directors, will also benefit from coaching and consultation. I’m excited to share some of my own learning and experiences with you here as well. 

One of the experiences that I am most excited to bring to Ezra is book groups for our faculty and staff as well as book groups for parents and community members.  

I participated in a book group over the summer for the book Bittersweet by Susan Cain. Cain focuses on urging readers to identify with a bittersweet state of mind as a way of reflecting on experiences and sharing space and moments with others. She shows that embracing this way of dealing with sadness and some of the more challenging aspects of life can lead to true creativity and even transcendence. I have been thinking a lot about the experience of reading this book with other school heads, especially when dealing with the loss of a close friend this past spring and I believe that there is an important lesson here about reflection and goal setting for a new year. 

Our age-group advisors work with our students to hone these skills. Through understanding our own strengths and challenges as well as high and low points, our students gain vocabulary and skill sets for not only being able to share with each other, but also for listening and giving support in an active way. 

We often tend to construct goals for ourselves as a way to improve or to overcome a challenge, but we also sometimes miss an opportunity to use challenges as space for change, both individually and as a community. 

In his book 60 Days: A Spiritual Guide for the High Holidays, Simon Jacobson writes about the importance of compassion and being sensitive to the souls of others leading up to Rosh Hashanah. Part of this is not being too hard on ourselves for the areas where we can improve. As we embark on a new year and a new school year, I want to bless us all with opportunities for growth and also to find ourselves in community with people who are also willing to listen to the more bittersweet pieces of our stories. I’m grateful to be in such a special community where we truly look out for each other and where listening is a value.


Wishing you and your loved ones a Shabbat Shalom and a Shanah Tovah, wishes for a sweet and healthy New Year!

Tani