Humility: a puzzling subject

I found myself laying awake two nights ago praying, and I quite suddenly came up with the notion that I hadn't been praying very humbly lately. This thought surprised me a little, leading me to contemplate its origin. I concluded this: When I think of humility, I think of laying down my pride, sacrificing for others, resisting thinking critically of others, admitting my downfalls...none of which are easy tasks or processes. Therefore, I set humility on a pedestal as something unattainable that requires me to act entirely contrary to my natural character. To pray humbly, then, I assume I need to be constantly contrite, confessing the countless occasions on which I completely failed. When I was praying that night, I wasn't doing that. I was happy. I felt guilty for having an amiable conversation with God.

What's wrong with this picture? It's totally screwed up, but then how should one humbly approach God? With what level of respect should we address him? We epically fail on a daily basis; what degree of repentance is required? How can that be incorporated with everything else we need to pray about--requests on behalf of others, requests of our own, praise, and our thoughts that we want to share with our friend and creator? On top of that, how does true (not idealized) humility work in everyday life? Christians are called to deny ourselves, but I don't believe that means to give up who we're made to be in pursuit of a "humble" stereotype--to be humble I need to morph into someone who never exerts opinions or feelings, tiptoes around so as to avoid stepping on people's toes, always working in the background, quiet, never noticed, never outspoken, rarely enthusiastic. After all, Jesus' teachings are anything but stereotypes. In fact, these qualities aren't necessarily what Jesus advocates. How then do we deny ourselves but retain our individual qualities which are so integral to the body of Christ?

There's something in me that thinks I can't be humble and enjoy myself at the same time...humility looks different for everyone, but how does it fit into my personality and character? I think it's like a puzzle. No one is a whole, complete, put-together puzzle until they get to heaven. While on earth, following Christ is the act of putting together the puzzle--we're given access to the pieces once we accept Christ, then we connect the pieces of prayer, Bible reading, serving, all the fruits of the Spirit, humility, etc. to reveal the image of God. Everyone's picture is a little different, though, and their pieces are shaped differently. I guess then that I'm trying to figure out what shape and colors my piece of humility possesses. It's a fascinating thought. I'd love to hear feedback if anyone thinks they can add something of value--on your experiences, what you've found true in your life, how you might disagree, or whatever else you'd like to share.