Lesson 2 - Behind the Curtain

Obstacles Shape Us

Part of what makes leadership so difficult is that it can be isolating. As Lindsay illustrates with a story about Nannerl Keohane, sometimes leaders are put in impossible situations, such as when Keohane was caught between her passionate student-demonstrators at Wellesley College and the school’s board of trustees. To make matters worse, leaders often can’t divulge the full story of their dilemmas, even when it would vindicate them or help others understand their decisions.

In fact, “a leader’s best work rarely sees the light of day,” as Lindsay puts it. That’s because leaders spend a lot of time and energy keeping bad situations from getting worse, or preventing bad situations from developing in the first place. Not only that, every leader suffers disappointment: a deal that fell apart at the last moment, a partnership that failed to materialize, a program that never got off the ground. 

And yet there is no good leadership without challenges. As Lindsay says, across the hundreds of interviews he conducted, every single leader remarked on a challenge that played a pivotal role in forging their character.


  • Take a moment to consider the course of your professional life. What have your greatest challenges been? What did God teach you about leadership through these difficulties? How did these experiences make you a better leader?

  • Think of a time when you did some of your best work behind the scenes. Why is this element of leadership so difficult?


Way back in the days of ancient Israel—long before “leadership” became its own booming industry with seminars, books, and philosophies—Moses collapsed under the weight of his responsibilities. His prayer of exhaustion will sound familiar to anyone in a leadership position: “I am not able to carry all these people alone; the burden is too heavy for me” (Numbers 11:14). If this is leadership, Moses goes on to complain to God, you might as well kill me.

Mercifully, God does not kill Moses; He gives him a team of confidants to help share the burden of leading God’s people (Numbers 11:16–18). And that’s why, as Lindsay explains here, “leadership craves companionship.”

Over the course of his research, Lindsay found that 96% of his subjects were married at the time of the interview. While it need not be a spouse in every case, effective leaders need trustworthy people in whom they can confide, especially as many leaders suffer from loneliness. 


  • Where in your professional or personal life as a leader does the burden feel too heavy for you? What leadership burdens are you trying to carry by yourself?

  • Where is there an opportunity for you to share your load with a confidant? Identify some people in your life with whom you can confide. What are some practical steps you can take to start sharing your burden?

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