Community resources for "Where do I go next?"

[DWSimmons]

Following up on the conversation in #meta:
I am unable to find a set of resources that answers the question of Where am I as a programmer? Where should I spend my time to pursue my goals? While a learn-it-when-I-need-it approach is common and successful, I don't believe it is effective or proactive.

Sites that provide challenges, koans, and practice often have some degree of pedagogy behind them. The "student" should have some context about where they are and some guidance about which projects will guide the leveling up.

I don't believe this pertains to the comp sci graduates or those that have learned another language.

Would a mind map or "arc" of concepts help?
Would code samples of increasing complexity help?
Would a self-assessment of Python skills help?
Would a fundamentals to specialization map help?
Would tagging challenges/projects/tasks help?

Is this a real need? If so, are the above or other suggestions going to address the need.