[csallen]

I've helped a few friends learn web development while in their 20s, a few of whom were highly intelligent MIT grads. I agree that the discipline and motivation are the biggest roadblocks, followed by discovering an efficient lesson plan (lots of places online will teach you the specifics without giving you the greater picture).

The fact of the matter is that when you have a lot of free time, you will likely end up frittering much of it away. If you absolutely adore programming and working on projects, then sure, you may spend those months productively, but not everyone can count on that. So it very much helps to have some external pressure — in the form of a job or a mentor — to help you push beyond limits that you might not choose to cross on your own.