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How to Fail Successfully

How to Fail Successfully

At the same time hopeful souls make their New Year’s resolutions, celebrating a bright future ahead, I failed dramatically. My dream faded away like the stage lights I knew I’d never see again. Oh, my youth, my song, my moments in the spotlight, my loud shouts and chords in small rooms, my nights of driving into the rising sun, my stumbling into providence, my comrades riding on the back of our ideals, my worn-in friendships, my creative sparks—these were now moments for my memories.  No one else saw her, but the fat lady against the back wall of the venue was now singing louder than the guitars could ring out. The party was indeed over.  

All of a sudden I was a broke and unemployed musician looking at the same board on which I had drawn my dreams six years earlier. In looking back at the story of my dead dream, I wondered if there was a right and wrong way to handle failure, and if how I handled failure could lead to my future success. It took a motorcycle trip across America to show me that this failure was a tool to use instead of an ugly truth to hide.

I have analyzed my failure and the failures of two mentors of mine to come up with a few things to remember when failure closes doors. A musician, a pastor and an entrepreneur use the same keys to rebuild different dreams. We have each proceeded to find a new dream that requires faith, results in adventure and reminds us of the power that God has to provide.


The first key to failing successfully is retreating. Take an extreme and extended retreat. I took a motorcycle trip across America for 38 days with a friend. The purpose of this road trip was to learn to be small. I had grown so concerned with my situation that I had forgotten how many other people there were in the world that didn’t care. I had forgotten about the farmers of the plains and the bakers making big city bread. I needed to watch people all over the country press on down their own paths, to learn that I am only one person in a world of others.

Know Your Goals

As I traveled, I wondered: What if my dream was broken on purpose? What if this was never supposed to work and was only meant to teach me one thing? I knew I could benefit if I could find out what it is. You can too. How are you going to use this time well? You and I don’t want efficiency and paid bills. We want to enjoy the deep things that life has to offer.  We want to dream again. We’d like to see some waterfalls.  

So, write down your goals and dreams and start checking them off. It will not happen if you don’t do it now. The relief is that now is all you have. It gives you a smaller frame to look through. Sometimes you have to find out what your path isn’t to find out what it is. So, instead of getting paralyzed, keep moving forward. A wise man told me while looking at a map on his wall, “You don’t have to decide what you are going to do for the next twenty years, you just have to decide what you are going to do next.”  

Maintain Perspective

The most important key to failing successfully is to be on watch. Open your eyes. Pray, and even fast, as you ask God to give your clarity on what He wants you to do as you take your next step. Fasting will teach you to live like you are desperate. Desperation has its greatest grip on those who are failures so we must use that to our advantage. In a state of healthy desperation, we are alert, on watch, and can live with heightened awareness on the path before us.

Also, when you hit bottom, lean on those who love you and let them know how much you appreciate them. Say it to their face. And when they go through their own moments of failure, be sure to return the favor.

During the months following my failure I swam to the depths of a phrase I had heard but didn’t truly understand, “I must decrease and Jesus must increase” (John 3:30.) Instead of letting your failures eat you alive, turn it around, and let this failure kill your fleshly desires. Grow joyful in your lack of control. Because in a life of faith, we can relinquish our control and feel peace. Because when Christ is our life, true success is not defined by our achievement, but by our reliance on Him. So, perhaps even in our failures, when we meet Him at the bottom, He can surprise us with success.

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