Here's an idea for enterprising web-devs with a lot more free time than me: an online service that manages a person's ongoing education with contemporary project management tools.

Once signed up to this service, I would like to be able to define educational projects with tasks, milestones, deliverables, etc. against which I can record and monitor my progress. If I specify dependencies and priorities, it can carry out wazzy critical path analysis and tell me what I should be working on and in what order. It can send me encouraging/harassing emails if I don't update it regularly.

Some use cases:

• I have enrolled in a formal course of study such as an undergrad degree. I can specify my subjects, texts, deadlines, tests and the like. It will tell me what I should be studying in what order, what areas I'm neglecting, and what I really need to get done before the coming weekend.

• I have recently started a new job, and have a package of technologies and skills to learn. Some are more important than others, or have much longer time horizons. If I have x hours a week to develop these skills, it will tell me what I should be doing with those x hours.

• Conversely, I am an employer or educator (or world-saving organisation) who wishes oversight of another person's study. I can assign them a prefabricated syllabus and observe their progress.

Some things that might fall out of a system like this once the infrastructure is in place:

• A community whose members can offer each other high-context support and advice
• A lot of useful and interesting data on effective learning routes through various subjects, perhaps powering a recommendation service

I imagine there are enough autodidacts and students on LessWrong to establish a preliminary user base. I for one would happily pay for a service like this.