Learning to Fail

Over a period of 12 years, I planted two churches in Williamsburg, Brooklyn. One church closed after seven long, hard years. It was one of the most painful and wounding experiences of my life. The other church grew rapidly and lives on, but leaving it has been confusing and lonelier than I could have imagined. Was one church a failure and the other a success? Was my longtime rootedness in a neighborhood a success? Was my tenacity in loving the poor and faithfulness in preaching the gospel a success?

If I’m honest, failure has caused me to question the goodness and even the existence of God, even months and years after the fact. How could God call me to this insanely sacrificial work, then let it fall apart? Did God fail me? And what about the people who love God but fail me by leaving or betraying me when I need them most? Can I really trust anyone? Apostolic, pioneering church planting is brutally challenging work.

For church planters and ministry leaders, success is difficult to nail down with clear measurables. Can it be measured by Sunday attendance, baptisms, group participation, service events, or years of faithfulness? Is success based on the opinion of my denominational leaders or group of elders or network or even my parents?

I’ve been a part of countless conversations with ministry leaders trying to redefine “success.” Many believe faithfulness is key. Success equals ministering according to your calling, not having a moral failure, living incarnationally in a neighborhood for a decade or more, or earnestly praying and preaching the gospel week after week. But what if we never baptize anyone? What if our neighborhoods are no better because of the presence of our church? Other leaders lean on the fruitfulness metric for success. Usually these leaders define success by their personal gifts or vision, which is code for, “whatever sets my ministry apart from other ministries” or “whatever ministry area where we’ve seen the most fruit.” Success equals unusually high Sunday attendance, effective community service events, or the number of responses to a Sunday sermon. After all, fruitfulness means that God is with us, right?

For many church planters, survival and sustainability is the measure of success. If I can just get this church planted and get it financially healthy, then I’ve been successful. This metric makes sense at first glance. I set out to plant a church right? So, if I plant a sustainable church, then I’ve succeeded. But what if my wife is miserable and making plans to leave me? What if my kids hate the church (and God) because it gets all my attention? What if the successful church I planted doesn’t actually portray the kingdom of God or the vision God gave me for a new church? What if I’m an emotional wreck or physically unhealthy or angry or bitter or spiritually dead? What if in the end, Jesus says to me, “Depart from me, I never knew you”?

The secular entrepreneurial world celebrates failure, because failure implies creativity, risk, and adventure. And failure leads to real learning and growth for a leader. We are church planters, creative entrepreneurs to the highest degree, Christ’s apostolic gift through the church to the world. Yet we start churches that are so safe, so alike, so vanilla, because we are so afraid of failure and so consumed by ideas of success. Seeking the kingdom of God is creative, adventurous, and risky work. It requires the kind of love that can’t be measured. Why are we so afraid of failure?

Honestly, “failure” has been the best thing that ever happened to me. It reoriented my identity as a child of God and uprooted my identity as a church planter for God. It taught me about the true upside-down nature of the kingdom of God. It created a deep longing for heaven, where all sadness, loss, and injustice will come untrue. It helped me understand people whose only hope is in the possibility of a better Story.

The cross was a failure. Jesus was a failure in the eyes of every single person in His society. As he hung on the cross, literally no one thought he was a success. Even after he resurrected from the dead, the cross was still considered “foolishness” whether measured by religion (Jews) or philosophy (Greeks). Every single educated person in the first century thought the cross made no sense. Yet the cross is our salvation. And the salvation of the world. And the singular picture of Divine Love.


Jesus tells us to “take up our cross and follow Him.” Could Jesus be saying, “Do something that will probably look like failure?” What if, as in the first century, literally every single one of us was wrong about success and failure? The kingdom of God always seems to be upside down compared to societal values and views, so why would success and failure be any different? God seems to love being subversive. All of His stories end with resurrection, which requires a death. The more wrecked and broken the person or situation, the more beautiful, weighty, and glorious its resurrection story.

Success is overrated. Way overrated. Yet everyone craves it. Loses sleep over it. Makes life altering decisions to pursue it. Manipulates or abuses people to protect it. Bends truth (lies) to try to portray it to others. Abandons a bold, kingdom sized vision to avoid failure or deals with deep depression because of past failures. Lives with overwhelming anxiety and fear at the thought of the mere possibility of failure.

What would it look like if we ministry leaders stopped worrying so much about “planting a successful church” and rather set our sights in pursuit of the kingdom of God, using wisdom to start communities that look for breakthroughs of salvation, discipleship, healing, justice, and reconciliation in our neighborhoods and cities? I believe this would lead to more perceived failure. Lots more failure. And more resurrections. I believe this would lead to a movement of truly creative and contextual church planting. I believe that church planters and their families would be much healthier in the gospel, and their churches would be much more generative.

God might just write “failure” into your story. When He does, He will also draw near to you in a way that will forever change your life. When you question his goodness and process your anger and fears, he will patiently listen. He will teach you that he is still with you, even if everyone else is gone. He will wrap his arms of protection and care around you, even if your church has mostly hurt you. And he will open your eyes to the forgotten, the poor, the helpless, and the “failures” among us by bringing us low to look each other in the eyes, to be fellow humans, and to long for a Savior together.

Church planting can be excruciatingly lonely. I cannot count the number of times I’ve stared at my ceiling in the middle of the night trying to mentally navigate a difficult church situation or trying to pray myself to sleep or trying to withstand the fiery darts of the Evil One. I think there’s real value in those moments, for the formation of character and growing dependence on God. But we also have each other. I wish we could get together to have honest conversations and to dream about possibilities of the kingdom of God. But this blog post will have to do for now. So, if you’d like, take a moment to share with us. Because your story matters.


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