Does it matter where you come from?

I've been wrestling with some theological stuff lately, and I would like to get some feedback on it. The stuff I've been wrestling with isn't the content of my theological thought, but is instead how to teach said theological thought, if it should be taught at all.

At some point in recent memory, my friend Amy - you can see her blog here - commented on the ways her fellow BSU-ers theology has changed over the years. I said something about how it would have been better if we would have known then what we know now. She replied by saying that that spiritual stage was good for us.

I'm torn on this. Was it really good for us to be borderline legalistic? Was it really good for us to be so foundationalist that we thought we grasped all the truth? Was it really good for us to be ignorant of the very complicated issues surrounding Biblical inerrancy?

Now, there were good things, too, about our faith back then. It was incorrigible in the sense that we would not abandon it despite the ambiguity life threw at us. It kept us safe and sane. It made us respectable. And it delivered us to the place we are today. It wasn't all bad.

But as I teach people in my church, especially the youth, I wonder how far to go. When they ask questions about the origin and interpretation of scripture, I wonder how far to go into textual criticism and hermeneutics. When they ask about the character of God, I wonder how far to go into theological concepts like Futurity, robust infinity, and God's relationship to evil. When they ask about Satan, I wonder if I should tell them that the Bible doesn't ever tell us that Satan is a fallen angel and that we really don't know what the heck he is or where he came from.

In short, I wonder if I tell them all the things I've learned through hard research and soul-searching if it would make them better Christians. In the Christian life, does it make a difference how you get to where you are? Does it matter where you come from?

In the now defunct Bonhoeffer book study, I came across an idea that stuck with me. Bonhoeffer says that a professor can assert after many years of work that knowledge is meaningless, but a freshman in college cannot make the same assertion. Is the same true for Christian spiritual maturity? If it is, why can't discipleship just be a workbook?

I don't know. I just don't know. On the one hand, part of me wants to teach all of the things that make me excited about Christianity. The scary part is that what makes me excited is seeing a new way of thinking about God that was different from what I was taught as a youth. On the other hand, another part of me wants to teach the same things I was taught - even though those things are borderline wrong and unscriptural - because that's where I came from.

So here's the question I wrestle with: Does it matter that I went from fundamentalist to post-conservative, or (with the proper teacher) could I have gone directly to post-conservative and saved myself 15 years?

What do you think?