Waiting vs. Taking the Risk

There are two schools of thought when it comes to knowing God's will. The first is to take the risk and see what God does. The second is to wait to "hear God's voice" before you do anything. I've taken risks, thinking that I heard God's voice and things turned out horrendous. I know people who pray to hear from God about every little thing....what shoes to wear, boxers or briefs etc. and that just seems to border on kooky to me.

So what are the practicalities of "hearing God's voice"? I know when I pray about just about anything I hear "No". This could just be a personality issue of someone who doesn't like to take risks (obviously, I do anyway). So how long do you wait? I read the Bible. Take quiet times. Meditate. Study... I get the feeling I could fast until I was a stick and still not hear God's voice..... The cost is just to great for my family and me for me to get it wrong again...