I partially agree. I think don't think God has no vested interest in our decisions... in other words, in many cases there is definitely a right and a wrong decision, or definitely something he specifically wants us to do. I think when we don't do it, or choose the other option, we suffer consequences in the form of setbacks or obstacles that we wouldn't encounter had we made the other choice. However, I agree that God looks on the heart and no setback will stop him from doing what he always intended to do, in fact, he knew the choice we would make before we made it.
I think Steve Jobs was right in a lot of ways. When I moved to Reno, I was a young christian who just received the baptism of the Holy Ghost earlier that year. I didn't hear God say this was the right choice, but I feared my parents being vehemently opposed. When they accepted the idea of it as though the decision was already made, and were supportive and encouraging, everything after that just fell into place. Looking back, I know that it was God's plan all along for me to go, but I wasn't very sure how to be sure of it at the time.
I believe if we acknowledge him, and in our heart honestly seek to please him and not our own desires, in some way he will lead us, and like you said, when we step out on faith, the assurance will come.