A Spiritual Map for the High Holy Days
- Aug 27, 2025
- 3 min read
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Rabbi Alan Lew begins his book This Is Real and You Are Completely Unprepared with a powerful statement:
Every soul needs to express itself. Every heart needs to crack itself open. Every one of us needs to move from anger to healing, from denial to consciousness, from boredom to renewal. These needs did not arise yesterday. They are among the most ancient of human yearnings, and they are fully expressed in the pageantry and ritual of the Days of Awe, in the great journey we make between Rosh Hashanah and Yom Kippur.
The High Holy Days are not just dates on a calendar. Rather, they are a pilgrimage of the soul, a journey of the neshamah. From the first shofar blast of Elul to the celebration of the world’s creation on Rosh Hashanah, and across the solemnity of Yom Kippur, we travel a path of awakening and change.
And like any real journey, it begins at a threshold, a place between what has been and what is not yet. The poet David Whyte describes this space beautifully in a 2016 interview with Krista Tippett:
The only place where things were actually real was at this frontier between what you think is you and what you think is not you… It’s astonishing how much time human beings spend away from that frontier, abstracting themselves out of their bodies, out of their direct experience, and out of a deeper, broader, and wider possible future that’s waiting for them…Half of what’s about to occur is unknown, both inside you and outside you.
This season invites us to stand at that frontier, to inhabit the threshold between the life we know and the deeper, wider future waiting for us. Alan Lew tells us that every heart needs to crack open. David Whyte reminds us that half of what is about to unfold remains unknown. The question is: how will we cross this threshold with intention?
Here are three markers for your journey which you may wish to consider:
Step One: Find Your Ground
Where am I standing in my life right now—what feels steady and what feels like a threshold?
What do I need to release to cross into the coming year more freely?
Step Two: Tend to Relationships
Who do I need to return to before the gates close?
Where do I need to offer forgiveness, and from whom do I need to seek it?
What relationship thresholds am I being asked to cross?
Step Three: Imagine the Future
Who am I becoming as I step into what is unknown, both inside and beyond me?
What unknown possibilities are waiting for us as a community this year?
What gift, small or large, can I bring to help us flourish together?
Every heart needs to crack open. Realness lives at the frontier between the known and the unknown. May this season give us courage to stand together – with openness, hope, and a willingness to be changed and expanded.
I look forward to seeing you at the DJC throughout the High Holy Day season.L’shanah tovah u’metukah – with blessings for a good and sweet new year,
Rabbi Ilyse Glickman
Please let me know what you think about today’s offering: rabbiglickman@djctoronto.com. I look forward to the conversation.
