Journey Into the Unknown | Chapter 6: Leading with Groundedness and Imagination
As we step into 2026, I'm thinking about what it means to lead with both groundedness and imagination—to hold the tension between roots and wings, between reverence for what has been and courage for what must come next.
The Discipline of Retreat: Leadership Begins in the Quiet
Before we can lead others forward, we must first learn to retreat inward. This isn't about escapism or self-indulgence. It's about discernment. The best nonprofit leaders I know—those building movements, reimagining congregations, creating justice organizations—understand that clarity doesn't emerge from hustle. It emerges from stillness. Retreating into the start of 2026 means asking ourselves the questions that shape everything else:
What work is truly ours to do?
Where have we been operating from obligation rather than calling?
What do we need to release so we can hold what matters most?
In a sector that glorifies busyness and measures impact in metrics, retreat is resistance. It's how we reclaim our purpose from the tyranny of urgency.
The Hard Truth About Leadership: Disappointing People at the Right Pace
A mentor once told me something that changed my thinking on leadership, and disappointment:
"Leadership is about disappointing people at the right pace."
This hit me like, What? Because as nonprofit and spiritual leaders, we're often the people who became leaders because we care deeply about others. We're helpers, healers, bridge-builders. The idea of intentionally disappointing people feels like betrayal. I have struggled with this personally. But here's what I've learned: Every meaningful decision creates disappointment somewhere.
When you shift your organization's focus to align with your mission, some donors will walk away. When you set boundaries to protect your team's sustainability, some stakeholders will push back. When you tell the truth about what's not working, some people will prefer the comfortable lie. Great leadership isn't about avoiding this disappointment—it's about pacing it with honesty, transparency, and care. It's about trusting people enough to tell them hard truths. It's about moving at the speed of trust, not the speed of transaction. The question isn't "How do I keep everyone happy?" The question is "How do I hold integrity while holding people's hearts?"
Tzimtsum: The Spiritual Practice of Making Space
In Kabbalistic thought, tzimtsum describes God's act of contraction—withdrawing to make space for creation. This has become a core principle in my coaching and collaboration: Sometimes the most powerful thing we can do is contract ourselves–our ego–to make room for others. In nonprofit leadership, this looks like:
Stepping back so emerging leaders can step forward
Asking questions instead of providing answers
Building systems that outlast our tenure
Centering community voice over founder genius
Tzimtsum invites us to go deeper, not wider—to invest in the quality of presence rather than the quantity of programs. To build relationships that can hold complexity, conflict, and transformation. This is how real change happens. Not through heroic individuals, but through spacious containers where collective wisdom can emerge.
An Invitation for 2026
As we move into this year, I'm holding these commitments: Clear vision over constant motion. Deep connection over shallow networks. Bold compassion over safe comfort. For nonprofit and spiritual leaders navigating unprecedented complexity, may 2026 be a year where we:
Lead from wholeness, not perfection
Build movements, not monuments
Trust the slow work of transformation
Remember that we are not martyrs—we are stewards
The world needs your leadership. But it needs you whole, not depleted. Grounded, not scattered. Aligned, not just achieving. Here's to retreats that clarify our calling. Here's to leadership that tells the truth. Here's to joy that sustains the journey.
With deep respect for the work you carry,
— Gather
