Christian Leaders: 3 Ways to Fail Well

fail forward fail well failure fear of failure success Feb 09, 2025

If there was a class called Failing Well 101, would you take that class? I would!

If I were to teach that class, here’s what I would teach.

(Some of these concepts are from John Maxwell’s book, Sometimes You Win, Sometimes You Learn for Teens--a book I am taking my leadership classes through this school year.)

Expect Failure

Do you wake up and expect to fail? Do you expect to make at least a couple of mistakes every day? I think maybe we do, but we don’t actually prepare our hearts and minds for those failures. Instead, we act shocked and surprised when we misjudge a situation, make mistakes, or fall short in some way.

As Christian leaders, we believe what Scripture teaches in Genesis--that the world is a fallen place and we are fallen people. That’s why it's unreasonable to go through our days expecting everything to go perfectly as though we live in a perfect world—we simply don’t. This is your mindset shift: expect things to go wrong. Not in a pessimistic or fatalistic way, but in a realistic way.

If you remind yourself at the beginning of the day and throughout the day that things are not going to go perfectly and that you will not be a perfect person, no matter how hard you try, it would take so much pressure off of you, wouldn’t it?

But it’s not just about expecting imperfection from yourself. Give other people permission to fail too—teachers, coaches, parents, friends, classmates, neighbors, cousins—anyone you interact with. Give them room to fail and give them grace. This is how Christian leaders should conduct themselves daily.

We are called to love as God has loved us. We forgive as we have been forgiven by God in Christ. Christian leaders expect to fail but also expect to receive grace. Give grace to the people around you who fail.

When Failure is Sin

I need to say this: if the failure you experience during the day is a sin—because all sin is failure, but not all failure is sin—what do you do? I want to remind you of what the Bible says to do.

1 John 1:9 says: “If we confess our sins, he is faithful and just and will forgive us our sins and purify us from all unrighteousness.” There’s your answer. Confess quickly. That verse should comfort you. You do not have to be afraid of failure. You do not even have to be afraid of sin because, yes, you will sin every single day. But the good news is that Jesus gives us grace and forgiveness every single day. That is the comfort you have as a Christian.

Root Your Failure in Your Faith in Christ

Another way to fail well is to root your failure in your faith in Christ. This is a privilege for those who are Christians, and for those who may not be, I hope this will give you insight into the difference Christian faith makes when you fail.

As Christians, we can detach our identity, self-worth, and personal value from our successes and failures. Our performance in life—whether in academics, sports, music, relationships, or any other area—does not determine our worth. Our self-worth is secure because it is in Christ.

Jesus lived a perfect life for us and paid for all our failures on the cross. Because of that, we are actually free to fail. We can afford to fail. This is something I talk about with my leadership class every year. It comes up over and over again because every day, we have to remember that our identity is not dependent on whether we succeed or fail. That’s why we don’t have to be afraid of failure.

Take healthy risks and fail. Your self-worth has nothing to do with whether you are doing well or poorly. Your self-worth is already complete. God sees you as completely righteous when He sees you through Christ. So put your trust in Jesus—that’s what it means to be a Christian. Christians can fail freely. You don’t have to attach your identity to your performance. That is a truly free place to live from and to lead from!

(I have a few videos about Christian identity on my YouTube channel - Check them out!)

Try To Fail (Take Healthy Risks)

So far, you have learned that failing well means expecting yourself and others to fail, but giving grace in response. The second way to fail well is to root your identity in Christ, not in your performance. Your failures do not define you, and neither do your successes.

The last way to fail well is to take healthy risks and actually try to fail. Only leaders would say this, right? But trying to fail means that you value failure. You understand that there is much to be learned and gained from it. Leaders not only accept the fact that failure will happen, but they take it to the next level and actively take risks, knowing they may fail.

One thing I tell my students regularly is to go and take a healthy risk this week. Come back next week and tell me how you failed. Tell me about the mistakes you made. Tell me about all the ways you were rejected and all the ways life didn’t work out for you this week. But also, tell me what you learned.

I literally reward my students—think Amazon gift cards—if they come back with a story of a risk they took, how it went, if they failed, what they learned from it, and how they grew from it. This is something I think we should do more often in schools, leadership classes, student councils, youth groups, and churches. We need to normalize failure!

Conclusion

From January through April, my students and I are going through "Sometimes You Win, Sometimes You Learn (for Teens)" by John Maxwell because conversation after conversation, class after class, these students are learning to talk about how they have failed—things they’ve done wrong, mistakes they’ve made, losses they’ve endured, and things they regret. More importantly, they are learning how to actually handle failure, not just minimize or ignore it.

As leaders, we need to learn how to handle, value, talk about, process, and appreciate failure. We need to recognize how God can use failure in this fallen world for the good of His people—that’s you and that’s me.

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Wazzup! I love helping middle & high school students to find & fulfill their God-given mission by developing Christian leadership values & skills. I work with students in 2 ways to strengthen their ability to lead their lives: 1) a bi-monthly leadership Mastermind group on Zoom (16 sessions over 8 months), and 2) a monthly 1:1 mentorship program via Zoom (10 sessions from August-May). Both are for students who are actively expanding their capacity for godly influence. Email me to learn more about how I can serve & support you! I'd love to connect: [email protected] --Brenda Jung, Founder of the Well-Led Life Leadership Program

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