Honestly, do I really expect to clarify this topic for us all in one posting? I think not. But I will offer some things I've been learning.
I think we overthink God's plan for our lives sometimes, as if God will only bless one thing in the whole world. Louie Giglio once mocked our attempts to find the center of God's will, then the micro-center of God's will, then the micro-micro-center of God's will.....
I think there are a few considerations though to guide our thoughts. First, we should certainly consider our giftings. This element is strongly emphasized in the modern church, with tests, etc. But I think we stop there too much. The next thing we should do is consider the need. Moreover, we need to consider what we would like to do. Yes, what would we like to do? We minimize that too much. In contemporary American Christianity, we too often think about where we would be miserable and then assume that's God's will. We think about what we'd like to do and assume that there's no way God would want that for us. He wants us to enjoy life (Ecc. 9:9a).
Finally, there's one element that I find never talked about. How does this or that option affect our character..drawing out Christlikeness in us or brutally exciting sin. Let's face it...we all have weaknesses wherein we would easily stumble in some capacities. Other situations draw the best from us. We should consider this last factor more. God is vitally concerned with our sanctification, our character formation. For as much as we talk about evangelism, we forget and ignore the maturing that God ultimately aims for. God wants ULTIMATELY to conform us to Christ. Let's consider that when seek to discern the Lord's will.