A Successful Failure?

In today’s entry in His Utmost for His Highest, Oswald Chambers makes a few excellent points. Namely, he reminds us that we are completely unable to learn to follow Christ as our True Savior until we realize that we are incapable of succeeding on our own. Chambers specifically quotes Matthew 5:11, a portion of Jesus’ Sermon on the Mount in which Jesus suggests that those who are “poor in spirit” (whatever exactly that means) will inherit the Kingdom of God.

That sounds fine and dandy at first read, and I’d even say that I agree with Chambers in his articulation and interpretation of this scripture. Yes, I understand I must seek Christ, and that He must intervene for me, and that I am completely unable to attain any sort of righteousness at all. I even understand that I must learn that I am, in Jesus’ words, “poor”, and I must learn this through, in Chambers’ words, stumbling over some obstacle that lies in my way.

So far so good. I need to be a poor spirit, which will lead to my sanctification through Christ’s saving me.

So, here’s where I’m confused.

How, exactly, does one live “poorly” in life when they are in a position of needing to be strong, decisive, confident, and willing to walk where there are yet no footsteps?

What I mean is this:  I have a life of leadership and trailblazing. I tread where there is no one yet to follow, but in a way which others will hopefully benefit by following my lead. Whether it be in business, or ministry, or even my role within my family, in order to succeed I must make decisions, on a daily and sometimes hourly basis, which require 100% faith in myself and in my ability to pull through. I often look beside or behind me to find friends and relatives who doubt the possibility of achieving the goal I am pursuing, or who think I’m crazy for trying. I find my peers telling me to move on, and find an “easier” way to go. But I simply cannot live life that way, distracted anything short of success.

If I could speak to Jesus face-to-face, I would ask Him how I am supposed t0 go about being a confident and strong leader, while relying on Him and understanding my “poor”ness. How do I have confidence enough in my own human faculties to continue to lead successfully, while understanding that I am incapable, fallen, broken, unworthy, and have (and will perpetually) fallen quite short of God’s intentions for my life.

How do I practically live life knowing that I am an utter failure but still have the confidence to present myself as a success?