Inertia is imparted upon our minds by culture, upbringing, education, friends, and other factors. In order to live freely we must be able to view ourselves critically and be able to reshape our beliefs. Fortunately, there are curricula that exist to accomplish this goal, and they work well. But I was thinking that there are many non-intellectual imprisonments that we suffer from, and there are fewer programs to address them. Two that come to mind are food and fashion. Yes, a motivated person could seek out magazines, books, and forums on these topics and expand themselves that way, but using these things and nothing more still makes it difficult, and that's assuming that a person would be highly motivated in the first place.
There's an additional factor that I think is less often recognized, but just as important. Comfort creates major inertia, and it's more than comfort--it has to do with your concept of self. Even if someone gives you explicit instructions about how to improve your diet or dress, the follow-through is not just dependent on your motivation--it depends also on your ability to venture outside of your comfort sphere. It's why the kids in the Wire wanted to go to McDonalds even after Bunny took them to that expensive restaurant downtown.