In the previous post, we looked at the nature of “wilderness” in the life of a leader. Wilderness is an empty or pathless area, wild and uncultivated—something bewildering—that can lead to a loss of bearings. We looked to the Bible for more understanding about wilderness as a motif. We learned that the wilderness could be both a geographical space and a state of being. It can be a solitary or lonely space where we feel deserted by others. A wilderness season is inevitable in the life of a leader.

A leader’s natural tendency will be either fight or flight. Either we disappear, or we attempt to double down on control. Unfortunately, neither alternative will serve our followers well.

We must gain a clearer picture of when we know we are in a wilderness season. Looking at the various narrative accounts in the Bible of leaders in the wilderness, every instance is depicted as an extended season of trial. Whether you read about Moses, King David, or even Jesus, as well as various other leaders, you see them go through a unique, intense experience, designed to test or prove each of them. It always includes one or more encounters with God.

In the previous post, I stated that wilderness was never meant to be a place of habitation—but it is designed to deepen dependence, learning, and preparation for what is next.

The Wilderness Requires a Shepherd

The wilderness motif in the Bible is often applied to sheep, both literally and metaphorically. The very nature of being a sheep requires the presence of a shepherd. Sheep are vulnerable creatures by nature and must be led to good pasture and water. They must be constantly protected from predators. A good shepherd provides clear direction, provision, and protection. The Bible often makes an analogy between sheep and people.

Psalm 23 provides a strong picture of how God longs to be our shepherd and the benefits of such a relationship. Therefore, as leaders, we should not give our full attention to the wilderness but instead, focus firmly on the shepherd of our souls.

Psalm 23

The Lord is my shepherd; I shall not want.
He makes me lie down in green pastures.
He leads me beside waters of rest.
He restores my soul.
He leads me in right paths
    for his name's sake.

Even though I walk through the valley of deep darkness,
    I will fear no evil,
for you are with me;
    your rod and your staff,
    they comfort me.

You prepare a table before me
    in the presence of my enemies;
you anoint my head with oil;
    my cup overflows.
Only steadfast love shall follow me
    all the days of my life,
and I shall return to dwell in the house of the Lord
    forever.

Notice the actions of the shepherd:

• He makes me lie down

• He leads me to waters of rest

• He restores my soul

Notice what the shepherd provides:

• His presence

• His protection

• His direction and rescue

Notice the blessings for the sheep:

• The shepherd’s security

• A community of others provided by the shepherd (the metaphor of the table)

• The shepherd’s promises of continuous love and belonging

This is all to our benefit as we travel through seasons of wilderness, leaning on the God of the universe as our shepherd. King David, the boy shepherd and who became the King of Israel, wrote this psalm. He understood the comparison of leadership to shepherding. But first, the leader must see their need for shepherding before leading as a shepherd. Ultimately a wilderness experience is more about who you are becoming then what you are able to accomplish. Below are some diagnostic questions you might find helpful in thinking through how your wilderness season affects you as a leader.

6 Questions for Your Leadership Wilderness Season

• How has your current wilderness season affected you as a leader? 

• How have you been changed by your experience in the wilderness as a leader—for better or worse?

• Choose one word that would best describe you as a leader right now?

• What one word would you choose to describe the leader you aspire to be?

• What do you think God is preparing you for as a leader?

• What do you think God is inviting you into during this season of your leadership life?