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The Leadership Wilderness: How to Turn Your Darkest Season Into Your Greatest Strength

Season of Preparation: A Letter to Leaders in the Valley

As we close another chapter of leadership, many of us find ourselves caught in that liminal space between what was and what’s coming. And if we’re honest, we’re a little anxious about what’s ahead.

There is a particular quality to these moments—these in-between spaces for leaders feel less like influential guidance and more like a grueling and grim experience. The precariousness of these seasons arrive unannounced. The people I know who lead with any authenticity, sometimes the communities they serve are less than amiable to change and growth. Thus, placing a heavy weight on the leader, to immobilize them to remain in a valley mindset, thus multiplying their darkness.

The Preparation You Did Not Choose

The wilderness has its own logic. When the Israelites left Egypt, they thought they were headed directly to promise. Instead, they found themselves in terrain they never chose, facing delays they never wanted. The logic was brutal in its clarity: separation before elevation. Preparation before the destination.

God knew what battles they were not ready to fight. This is the part that cuts deepest—the recognition that our urgency is not always aligned to readiness. We want to rush toward what’s next, but the wilderness operates on its own timeline, indifferent to our schedules. I think about leaders I have known who tried to shortcut this process and who mistook their impatience for righteous ambition. Their struggles and setbacks were spectacular, not because they lacked talent or vision, but because they hadn’t fully inhabited the space they had been given. This is a lesson for my younger self. My most challenging moments in leadership, were lessons masked as isolation and prejudice.

To be where your feet are is to acknowledge that this moment, however uncomfortable, however uncertain, has been authorized by forces larger than your planning. God specializes in alchemy. He takes the raw material of our suffering, disappointment, doubt and transforms it into something that serves not just us but those who come after us.

Let me be clear: your presence where you are is not accidental. The kingdom needs you here, in this space, with these people, facing these particular challenges. Leaders should be able to want success so bad, that the setbacks are breadcrumbs to greater purpose. To put it simply, the psychological attacks, and coercion you are experiencing, is the roadmap through our season of preparation. 

The Testimony of Presence

To be where your feet are is to practice a radical form of faith. It is to trust that your wilderness has an expiration date, even when you cannot see the exit. The road we travel, both personally and professionally, is not easy. Our ascension from the valley comes not by avoiding the valleys, but through learning that our faith is found there.

As we find ourselves in the valley, it is difficult not to internalize that our every move is punishment. But it’s preparation. When you catch yourself thinking “I’m stuck here,” replace it with “I’m planted here.” When you think “Nothing is working,” ask instead “What is this teaching me that I couldn’t learn anywhere else?” The wilderness is not where good leaders go to die—it’s where great leaders are forged.

Stay. Cook. Serve.

Your people need what you’re preparing.

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