Last time I talked about Jesus’ statement that anyone who wishes to follow him must “deny himself”.
Let’s take a fresh look at what Jesus is saying in these verses, and ask him with open hearts what he really wants us to take from them.
Taking Scripture out of context can have bad results...
Context is always a good place to start.
The context here is that Jesus told his disciples that he was going to be crucified. Famously, Peter thought this was not such a good idea. So he pulled Jesus aside and rebuked him for saying that he would be killed. Jesus’ response: “Get behind me Satan! You are a stumbling block to me; for you are not setting your mind on God’s interests, but man’s.” (Mt. 16:23)
Then Jesus uttered his words about self-denial. I suggest to you that self-denial means setting your mind on God’s interests over your own. The point is not that you should despise or insult yourself. God is not glorified by self-contempt, and nothing in this verse suggests you should hate yourself. The point is that you should be like Paul’s disciple, Timothy:
For I have no one else of kindred spirit who will genuinely be concerned for your welfare. For they all seek after their own interests, not those of Christ Jesus. (Philippians 2:20)
The point isn’t that you are scum and that you’re interests are stupid and worthless. The point is that Jesus is amazing, and his interests and values are worth your life!
That's a little better. Still technically out of context though...
Jesus’ message is that we should let go of our preconceived ideas of what our lives are about. When he says that the only way to find your life is to lose it for his sake, he’s saying that in order to have the life that Jesus wants you to have, you have to let go of what you thought your life was. Maybe you have an idea in your mind of what the story of your life is about. Denying yourself and giving your life to him means giving him permission to hit “delete” on that whole story and rewrite it from scratch.
This also leads into his words about “taking up your cross”. Jesus is saying that, as Christ-followers, we must remember that suffering is a crucial part of the story that we are entering into. The story that the Father wrote for Jesus’ life on earth did not just include, but centered upon, great suffering. The story that he will write for your life does too. Will you let go of your story (in which you are insulated from suffering, pain and difficulty) and take up his?
Apparently Superman likes the story he's already got. How about you?
To “deny yourself” doesn’t mean to hate yourself – except in the sense that Jesus uses it in Luke 14:26-27 (quoted above). If you think Scripture teaches that we should hate ourselves, then this verse also explicitly commands you to hate your mom and dad, your spouse and children, your brothers and sisters as well. But people who know much more about the Ancient Greek language than I do make it very clear that Jesus is using hyperbole to show that He must be first in your life, and that your devotion to him must far outstrip your devotion to anyone else. Scripture clearly commands that you are to love not only your family members, but everyone, – including yourself. (Leviticus 19:18)
Snapshots of Glory 
This morning, just before reading your post, I was reading Perelandra, chapter 10, where the un-man is tempting the woman to think of herself as the lead character and author of her own tragedy. Jesus’ rebuke of Peter, in calling him ‘Satan,’ was that he was thinking as men do, NOT as demons do. Satan does not want us to worship him so much as he wants us to worship our roles here on earth. In addition to suffering, Jesus going to the cross was an act meant for the next world, while Peter was calling Jesus to remain here and cling to His role on earth alone.
To ‘see the things from God’s perspective,’ and not from mans, is to see the full picure, heaven and earth, suffering and victory, God and ourselves, and not to go the route of man: painless, quick, self-important. In Perelandra, the un-man attempts to seduce the woman into a noble suffering to make her own name great. This is a mindset I see in motion today. Rather, I believe God wills us to make His name great, the presence of suffering or ease is trivial.