Why “Wintering” in Summer Is Essential
By Ellie Starr, Chief Executive Officer / Founder
What if rest is one of leadership’s greatest responsibilities?
When I returned home from France this summer, I brought back more than gifts, memories of leisurely meals, and perhaps more rosé than I should admit. I also carried home a question that outlasted the jet lag: Why do so many leaders avoid taking time off to rest and truly unplug?
Reflecting on my time away, I returned to one of my favorite books, Katherine May’s Wintering: The Power of Rest and Retreat in Difficult Times. Although it isn’t a leadership book, I find myself reading it through the lens of my work with nonprofit leaders.
May reminds us that winter is not an interruption to life but a necessary part of it. Seasons of slowing down, reflection, and restoration are not evidence that something has gone wrong. They allow new growth to emerge. As she writes, “We have seasons when we flourish and seasons when the leaves fall from us, revealing our bare bones. Given time, they grow again.”
“Wintering” need not be confined to a particular time of year. I think of it more broadly as the practice of stopping, sitting still, and resting—and summer often offers us an opportunity to do just that.
That perspective stayed with me throughout my trip. Extreme heat and fires disrupted our plans, forcing us to be more still. We spent afternoons inside with AC taking siestas and evenings in deep conversation, listening to one another over the sound of cicadas.
I wasn’t simply experiencing a different pace of life. I was being reminded of something we too easily forget; rest is not something we earn after exhausting ourselves. It has its own purpose. It creates space for perspective, creativity, and renewal.
What might nonprofit leadership look like if we approached rest with the same intention we bring to every other investment in our organizations?
Our sector is fueled by purpose and shaped by urgency. There is always another fire burning, meeting to prepare for, donor to call, or challenge demanding our attention. The work is deeply meaningful, but it rarely pauses. Somewhere along the way, many of us have begun to equate constant availability with our commitment—as though leadership is measured by how much of ourselves we are willing to give away.
Yet the leaders who have influenced me most are not memorable because they worked the longest hours. I remember them because they brought clarity to complexity, wisdom to difficult decisions, and steadiness when others felt overwhelmed.
Those qualities do not emerge from exhaustion. They grow through reflection, perspective, and a willingness to step back long enough to see what constant motion obscures.
This has caused me to think differently about organizational capacity. We devote considerable attention to staffing, governance, fundraising, strategic planning, and financial sustainability—and rightly so. Strong organizations need strong systems. But they also need leaders with the capacity to lead and teams with the energy and perspective to follow creatively.
If leadership is among an organization’s greatest assets, shouldn’t protecting the capacity to lead be as important as strengthening every other part of the organization?
A vacation alone is not the answer. Rest is broader than time away. It is the intentional practice of creating space for reflection before exhaustion becomes the norm. Renewal is not a reward we earn once the work is finished; it is a discipline that enables us to continue doing the work well.
Nor is this true only for leaders. Leaders are responsible for creating cultures in which their teams can pause, rest, and rejuvenate. The idea is hardly new—a regular day of rest is as old as religion—but perhaps we need to see it through a new lens.
What if protecting our capacity to lead were not something we did after the work was finished, but part of the work itself?
Perhaps rest is not stepping away from leadership at all. Perhaps it is one of the ways we honor it.