Gideon's track record in fearfulness tells a powerful tale of just how irrational fear is and the crazy sorts of backwards things it can make us do.
When we first meet Gideon, he's threshing grain in a winepress. These are not familiar terms for most of us, who buy our grain already threshed and our wines aged, but what's important to know is the blueprint of these places. A threshing floor was a large, flat, open area of land that was good for beating the wheat to separate it. It was usually specifically built and might be ringed by rocks to set it apart from the rest of the farm property, but there wasn't a lot of shelter for a threshing floor; it was simply wide open (and had to be). A winepress, on the other hand, consisted of two large vats for pressing grapes. So there was at least some equipment lurking around there. When we talk about Gideon hiding in the winepress, we're likely talking about Gideon hiding in one of these vats.
Go back for a second to this story (Judges 6) - Gideon was hiding in the winepress, threshing his wheat there because he was afraid of the Midianites, who had already stormed through Israel and destroyed most of the crops. This enemy army was wreaking havoc on Israel, and Gideon was trying to preserve both his meager measure of grain and his very life. He feared what would happen if the Midianites came upon him on the open field of his threshing floor...so he crawls into an enclosed vat.
At least in an open field, he has a fighting chance of making a getaway! If they find him in the winepress, he's trapped.
Then God tells him to tear down the altars of his father, the offensive altars to the Baal gods. And here again, Gideon is scared. He's so scared that he won't do it in the light of day, lest he get caught in the act. So he waits until the dark of night and sneaks out to tear down the altars.
...Most persons would be afraid of the dark! Not only that, but without much light to see by, he's more exposed to anyone who might catch him because even though he thinks they cannot see him, he cannot see them. Once again, in an effort to escape his fear, he's trapped.
And then comes the most ridiculous scene of all. He's standing on the edge of the Midianite camp with his God-selected 300-man army, poised and ready to defeat the enemy and claim a victory for Israel. But he's still scared. He's still not sure about all of this. So God tells him that if he's scared, he can sneak into the Midianite camp and just listen to what they're saying about him. Then, he will know that this whole adventure is legit.
So Gideon - fearful, afraid, scared-out-of-his-shorts Gideon, leaves his 300-man army behind and sneaks into the enemy camp with just one soldier to see what they're saying about him. It doesn't make any sense! He's afraid to fight them, but he walks right into the midst of their camp without backup? This seems like a good plan to him? This seems like the right response to fear?
At every turn, Gideon is afraid. And at every turn, his fear leads him to do something more dumb than whatever just facing his fear would have led him to do. He's afraid to be found in the open field, so he hides in an enclosed vat. He's afraid to be found out in the day, so he destroys idols in the night, when he cannot see anyone who might sneak up on him. He's afraid to fight the enemy, so he strolls leisurely into their camp to catch a bit of their conversation. And at every turn, he's probably completely unaware how foolish his fear is making him. He probably doesn't know how ridiculous his response to fear is.
It's irrational. But then again, fear almost always makes us do irrational things.
That's why it's best we just own our fears, then face them. That's why it's best we don't let fear change what we do. Because most of the time, what seems like a good idea in response to fear is actually incredibly silly and puts us in greater danger than what we were afraid of in the first place.