“Blessed are those who mourn, for they will be comforted.”
Matthew 5:4 (NET)
If you’ve ever held a leadership position—whether in an organization, church, community, politics, or your own family—you know that leadership can be challenging. Leading is painful, and Jesus was unequivocal that kingdom leadership is cruciform:
But Jesus called them and said, “You know that the rulers of the Gentiles lord it over them, and those in high positions use their authority over them. It must not be this way among you! Instead whoever wants to be great among you must be your servant, and whoever wants to be first among you must be your slave—just as the Son of Man did not come to be served but to serve, and to give his life as a ransom for many.” (Matt. 20:25-28, NET)
I once heard a preacher say that marriage was God’s sneaky way to get us crucified! I think the same is true of leadership. Yes, there is so much joy in leading: shaping and influencing people, directing mission and accomplishing goals, and building a legacy to be proud of. But with each of these, there is a corresponding trial by fire. Leading exposes our insecurities and inadequacies. We experience hurt, betrayal, rejection, and misunderstanding. Relationships once treasured break, with no repair in sight. We get caught between our affections and our duties and must make a painful choice. Sometimes, people simply refuse to ascribe charitable, noble motivations to our actions and decisions. And when we do make mistakes or misjudgments, there is no grace to be found. Leadership is God’s sneaky way to get crucified.
Unfortunately, our modern leadership culture leaves us no room to mourn our pain. We are expected to “be professional,” whatever that means. We expect our leaders to be thick-skinned, to “man up,” grit their teeth, and carry on, unaffected by the challenges we have faced.
But I don’t believe this is realistic or healthy. Human beings are simply not wired this way. I believe that anything that doesn’t comport with the basic ways God made us as his image-bearers is disintegrating and destructive. I desire to embrace a leadership principle that creates space for a truly human experience, one that resists the John Wayne leadership ethics we’ve inherited. I long for those things to be disentangled from our vision of what is good leadership. And I don’t think I’m the only one.
Jesus says those who mourn are blessed! They are in a state of human flourishing. The Greek word translated as blessed (makarioi) does not mean happy or naively optimistic. It carries the weight of divine favor and true well-being in God’s kingdom. Jesus says that those who don’t hide or suppress their discontent or pain, but who honestly express it in lament, will be comforted. The Greek passive verb “to be comforted” (parakaleō) is in the future indicative, which means it conveys the certainty that God will draw near to those who mourn to encourage and comfort. It has the same root as the name Jesus gives to the Holy Spirit, the Paraclete or the “Advocate” (John 14-16).
Jesus describes the Advocate’s ministry:
“But I tell you the truth, it is to your advantage that I am going away. For if I do not go away, the Advocate will not come to you, but if I go, I will send him to you. And when he comes, he will prove the world wrong concerning sin and righteousness and judgment—concerning sin, because they do not believe in me; concerning righteousness, because I am going to the Father and you will see me no longer; and concerning judgment, because the ruler of this world has been condemned.” (John 16:7-11)
Jesus is saying that God will personally draw near to those who mourn and will comfort them as an Advocate, one who defends, vindicates, and makes them whole (reintegrates them, putting back together what has been shattered in them). To mourn honestly is to recognize that our whole being is wholly dependent upon God, who alone can defend us, and to affirm the image-bearing nature of who we are despite the demeaning and berating words, actions, and hostility leveled against us. Mourning and deep trust in God, our Advocate, go hand in hand, so that mourning truly is a state of flourishing in God’s kingdom, even when it doesn’t feel like it.
In leadership, we need a language of discontent. There are proper times and places to express our lament, and we must be wise about how and to whom we express it. But the opposite extreme, not expressing it at all, is equally destructive, if not more so, to our personhood and our vocation as leaders and leadership teams who image God. Jesus does not give us that option. Rather, he calls us to believe that he is present and active in our suffering. He wants to meet us in that pain and confusion and, through it, show us greater, more beautiful vistas of who he is, who we are in him, and what he is working for good through the struggle.
I recognize that learning a language of discontent is like learning a new language. It is unfamiliar at first, and we may feel awkward, foolish, and even a little skeptical as we step into this kingdom ethic of lament. As with any new language, we may occasionally make mistakes as we learn to navigate this unfamiliar world together. This has to be a language we learn together, taking risks, extending grace, and drafting our explicit norms as we grow. As we do, let me offer the following 10 practical steps to develop our team’s language of discontent.
Acknowledge that leadership is painful rather than pretending otherwise.
Leaders must begin by naming reality instead of suppressing it.
Give yourself and others permission to mourn instead of “being professional.”
Reject the cultural expectation to be unaffected.
Practice honest lament before God.
Lament is not weakness; it is the path to divine comfort.
Reflect on your experiences of hurt, betrayal, and misunderstanding.
Name them specifically rather than glossing over them.
Create intentional spaces for processing pain.
This may include journaling, spiritual direction, counseling, or trusted peer conversations.
Reject “John Wayne leadership ethics.”
Actively unlearn cultural scripts that demand stoicism and emotional suppression.
Embrace your humanity as part of imaging God.
Recognize that suppressing emotion is dehumanizing and spiritually destructive.
Trust God as Advocate in your mourning.
Let lament lead you toward dependence on God rather than self-protection.
Normalize lament within your leadership culture.
Model it so others know it is permissible and healthy.
Integrate lament with servant leadership.
Let mourning shape you into a more compassionate, cruciform leader.
