Poor Gideon. He seems to be considered a bit of a coward, hiding from his oppressors in a winepress, demanding signs from God before taking any action, and then waiting for the cover of darkness to do so. "Look at Gideon," I’ve heard some people say, "he should have trusted the word of God and been bold enough to just go and knock down that Asherah pole then and there."
When the angel of the Lord appeared to Gideon, he said, “The Lord is with you, mighty warrior.” … “Pardon me, my lord,” Gideon replied, “but how can I save Israel? My clan is the weakest in Manasseh, and I am the least in my family.” (Judges 6:12 & 15, NIV)
I can relate a little bit to Poor Gideon. His threshing wheat in the winepress idea looks a lot like my hiding a lamp in a bushel idea. I often find myself asking God "Are you sure?", doubting that I've heard him right when I'm surrounded by people with far greater skills, talents and experience than what I have. I’m conscious of my own inadequacies, I feel I have the least to offer.
There's nothing in the text that tells us Gideon was wrong to ask God for His reassurance. The author of Judges accuse Gideon of cowardice. Instead we are shown how God can use the least of us for His greater glory.
God knows that when He calls the least qualified that extra encouragement and reassurance is needed, and in His grace provides it in the right way and at the right time. An offering supernaturally combusts, fleece is dry instead of wet then wet instead of dry. At the greatest challenge - a numerous enemy faced with only 300 men - an overheard conversation provides the necessary boldness and inspiration. An enemy is dispersed without a sword being lifted.
The less I have to offer, the more room there is for God's Spirit to move instead.
It is not for me to fight the battle, I am just asked to stand and blow a trumpet and shout and hold my torch high so it can be seen.
Courage is not the lack of fear and doubt, it is stepping out in spite of those doubts. And courage grows out of encouragement. It's okay to ask God for reassurance and encouragement when faced with challenges, in His mercy and grace they will be given to me.