I once heard, and I forget who was being quoted, that "the most important thing about you is what you think about God." It seems to me, as I reflect on some of the personalities I've encountered, that there are generally two kinds of people.
There is one kind of person who believes that God is a whole lot like them. They are usually very logical thinkers. They think through their situations and evaluate their situation by putting together all of the information and however it fits together neatly will orchestrate how they act upon it. It seems obvious to them that God thinks the same way. To them god makes sense, He wouldn't want them to do something that doesn't benefit them in the long run. God wouldn't want them to take risks. It is rare that someone like this would become a missionary or sell all of their possessions and give it to the poor. This sort of action is illogical and therefore can't be God's will.
There is another extreme personality. This is the person who believes they are nothing like God. They think one of two ways: either they believe that God is so Holy and they are so evil that they can't relate to God or they believe that God is just too far away for it to matter. They believe either that it's impossible for them to be anything like God or they are just uninterested in finding that out. This person doesn't usually consult God in any serious way before taking action. Yes of course they pray sometimes and ask God what He wants them to do but in the end they continue believing that God is indifferent. They might go and be a missionary but it usually won't be because they truly feel called to do so. They will do it because it seems to be the obvious best thing to do to please God. God wants them to be miserable in serving Him because to be happy wouldn't be what God wants for them, He's too holy to care about our happiness. They will serve God in the big obvious things but when it comes to daily life their connection to God is distant.
Really, both sides of the spectrum have a distant connection to God in all practicality. The first never listens to God because they think they already know what God is thinking. The second doesn't listen because they believe they'll never really know what God is thinking.
I suggest that there may be a third group; one we should aspire to. They listen to God no matter how confusing He may be to them and they understand that no matter how small the situation God is close by. God really cares about what choices you make so He desires to guide you but He's just as mysterious as He always has been. This group is open minded. They are willing to take the risk for God but they also understand that God is concerned about them. They understand that they can be like God and they are like God. By the cross we have been made like Him. He has redeemed us, brought us back to who we really are; the image of God. This third group understands that they are not striving to be like God, they are striving to be themselves, because the real them is already like God. But at the same time we are not God. Only God is truly God and the goal is for Him to dwell with us and be our God, not for us to be God. Since we are not God and never will be, His will is not always clear. He is mysterious enough to keep you guessing. The third group understands this and therefore approaches God humbly realizing that they can't assume God's will just because it sounds logical but at the same time they understand the closeness of God and His accessability. They have humility, unlike the first group, and they understand that they are in relationship with God. God's presence soaks our lives but His will remains mysterious.
Consider Jesus in the Garden of Gethsemene. He is praying in agony and desparation, even sweating blood, seeking God's will. He of all people should assume God's will, He's the incarnation of God. Yet He still seeks, He's still humble. He understands His will and God's will are different somehow praying "everything is possible for you. Please take this cup of suffering away from me. Yet I want your will, not mine" (Mark 14.36). He understands that God doesn't necessarily think like Him. Yet He also recognizes His closeness with God praying "just as you are in me and I am in you" (John 17.21). He knows who He really is; The image of God, yet seeks God's will with unique humility. We should identify with Jesus prayers before His death.
God is not easy to hear or understand. He is difficult and He is confusing. But He is mysteriously accessible, He believes we can be like Him and He is as close to us as your very next breath of air. He is leading us toward His mysterious goal which is ultimately the healing of the world.