Freedom and accountability
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Every pastor needs to address the issue of freedom and accountability. It's part of the pastor's role in nurturing a church community: neither a laissez-faire atmosphere nor a judicial one helps people grow as disciples.
So much of our cultural angst and chaos has to do with how we view this subject. In our culture, people advocate extremes of both freedom and accountability. Unfortunately, the church's position often isn't much better considered than the broader culture's. If you haven't preached or taught on these themes before, be cautious about trying to load all you want to say onto this parable of the ten maidens. Raise the questions, and develop them with the congregation over time.
One reason accountability and freedom are important issues in a congregation is the range of ages represented: people of different ages consider these questions quite differently. But the Christian faith is dynamic and flexible across generations, cultures and contexts. It's critical for pastors to to help people with these issues as they grow, mature and change.
Cultivating an honest and vigorous community--one that honors the individual without being individualistic, that honors the community without surrendering to group-think--is central to our pastoral calling. It is very difficult to do. Inside and outside the church, it's easy to fall prey to extremes. But the way of Jesus holds on both to freedom and accountability with passion and commitment.