Kierkegaard is pretty great. Just throwin' that out there.
I've been all into Fear and Trembling these days and it's surprisingly consistent with my own experience. One thing that's particularly striking is how Kierkegaard writes that faith is not something we can easily communicate. We cannot express it in mere words. I've definitely faced this in the last few months. Words fail. Expression is impossible. Any noise I might let loose falls short of conveying the truth and conviction of what I know in my head and my heart. I've been driven into spells of silence. Not going mute, but succumbing to the feeling? passion? thoughts? (even now words are insufficient for me to say what I mean) that are overwhelming. I can hardly describe them to myself, much less another human being.
Kierkegaard also describes faith as something beyond mere resignation of what we cannot sustain on our own. Abraham did not merely sacrifice Isaac with no expectation that God would do something great through it all. He didn't just "let go" or "give up." The difference is that he expected--he had faith--that God would follow through with His promises even though the obvious means were gone. Perhaps true faith was even the very specific expectation that, though God was taking Isaac away, He would surely give him back somehow.
The question comes, though, regarding specificity and subjectivity. When we seek God in faith, can we come to Him with great expectations that very specific desires of our heart will be fulfilled (though, perhaps in His time)? Or do we give Him a ton of slack, acknowledging that He will in some way fulfill our happiness, whether in this life or the next.
The former option requires a lot of wisdom. In fact, it seems irrational to others (perhaps why we fail to communicate it well.) These are things we desire that couldn't easily be explained away. What we ask for--expect, even--are almost miracles. And yet, we can't go wishing things completely subjectively, arbitrarily even, and say that God will bring it about because we "have faith." Perhaps we go on with this "faith" through the rest of our lives, living in perfect "confidence" that God will give us our hopes and desires. But then we die and discover that, though good things have come and more good awaits, in this specific instance we have been deluding ourselves. We lived in illusion and to God's disgrace, we dubbed it "faith."
The latter option seems to be entirely irrelevant in its vagueness. If we hope in generalities, thinking "whatever comes, God will work it out," it will no doubt become true. But there is no test in that, no determination, nothing to try a person and test their trust and dependence on the Father. As the Cheshire Cat said to Alice, it doesn't matter what road you take if you don't know where you want to go. We almost make our God too little by giving Him little expectations. Ask for big things and see what He gives you.
So I suppose it comes down to discernment. We can't be arbitrary, but neither can we be limited. Pure reason falls short, but mere feeling or intuition is absurd. Faith is the grey area where we seek Him, give all for Him, and acknowledge that when it all works out, it's because He acted on our behalf. "Likewise the Spirit helps us in our weakness. We do not know what to pray for as we ought, but the Spirit Himself intercedes for us with groans that words cannot express... He who did not spare His own Son but gave him up for us all, how will He not also with him graciously give us all things?"