One of the unexpected gifts of returning to rabbinical school at this stage of my career has been discovering how often ancient Jewish texts refuse to stay politely confined to the beit midrash.
As I begin wrapping up my studies at the Academy for Jewish Religion, I have found myself increasingly fascinated by the unexpected ways Jewish texts continue to shape how I think about the professional work that occupies much of my life. Lately, that has meant discovering that one of Judaism’s most famous mystical stories may hold surprising lessons for something far less mystical: strategic planning.
Or at least strategic planning in Jewish schools.
For the last several months, I have been studying the famous story of Arba’ah Nichnesu LaPardes – “Four Entered Pardes” – found in The Babylonian Talmud (Chagigah 14b). The story itself is well known.
Four sages entered Pardes, often understood as a mystical encounter with divine or transcendent knowledge.
Ben Azzai died.
Ben Zoma lost his mind.
Elisha ben Abuyah emerged transformed so dramatically that tradition remembers him thereafter simply as Acher, “the Other.”
Only Rabbi Akiva entered in peace and departed in peace.
For centuries, readers of this text have understandably focused on the obvious question: what exactly happened in Pardes?
But in my recent studies of Jewish mysticism, I have found myself increasingly drawn to what I think may be the more interesting question.
Why did only one emerge whole?
What was it about Rabbi Akiva, his disposition, his preparation, or his capacity for discernment that allowed him to survive an encounter that left the others irreversibly changed?
And perhaps more importantly: what happens when we begin asking similar questions about institutions?
In my consulting work with Jewish schools, I often watch organizations approach strategic planning as though the plan itself is the work.
We gather stakeholders. We identify priorities. We build ambitious visions for the future. We talk about innovation, transformation, growth, and change.
But perhaps the real question is not what future the institution hopes to build.
Perhaps the more important question is whether the institution is actually prepared for the encounter with change itself.
Because transformation is disruptive.
Like Pardes, change rarely leaves institutions untouched.
We often imagine strategic planning as the mechanism that creates transformation. But increasingly I wonder whether strategic planning simply reveals what already exists within an institution.
Healthy schools entering ambitious change processes often emerge stronger, more coherent, and more aligned.
Fragile institutions entering the same process may become overwhelmed by competing priorities, internal conflict, weak governance, leadership misalignment, or uncertainty about identity.
The strategic plan itself does not determine the outcome.
Like Pardes, the encounter often amplifies what was already there.
The parallels become difficult to ignore.
Some institutions, like Ben Azzai, attempt too much too quickly. The ambition itself becomes unsustainable.
Others resemble Ben Zoma. Faced with too many competing priorities and insufficient internal coherence, the complexity overwhelms the system itself.
Some experience a version of Acher. In the process of transformation, they drift so far from their mission and identity that they emerge fundamentally disconnected from the very purpose they were originally created to serve.
And then there are the Rabbi Akiva institutions.
Organizations grounded in trust. Institutions with strong governance. Leadership teams aligned around shared purpose. Cultures resilient enough to tolerate uncertainty. Communities capable of holding difficult conversations without fragmentation.
These institutions can enter transformational processes and emerge stronger not because the strategy itself was superior, but because they possessed the internal discipline necessary to survive the encounter.
Perhaps strategic planning asks the wrong first question.
We tend to begin by asking:
Where do we want to go?
But the story of Pardes suggests another possibility.
Before asking where we are going, perhaps we should ask whether we possess the internal discipline, trust, leadership capacity, and institutional coherence necessary to survive the journey itself.
In Jewish mysticism, the danger was never Pardes itself.
The danger was entering unprepared.
Schools, I suspect, are not so different.
This has quietly become one of the unexpected joys of my rabbinical studies. The more time I spend immersed in Jewish texts, the more I discover that ancient wisdom has an uncanny habit of following me back into boardrooms, strategic planning retreats, and leadership coaching conversations.
And perhaps that is itself a reminder.
Jewish texts do not only teach us how to pray, how to believe, or how to live meaningful spiritual lives.
Sometimes they remind us how to lead.
And occasionally, they force us to confront the uncomfortable truth that success depends less on where we hope to go than on whether we are prepared for what the journey itself will demand of us.
Not everyone who enters Pardes emerges whole.
The same, I have increasingly come to believe, may be true of strategic planning.
