How can we make online Help as natural as breathing?

One of the themes of every Help related conference is that some users are reluctant to use Help. Help, as a word, implies failure and, it is said, Microsoft spent a lot of time trying unsuccessfully to come up with a better word to use.

Recently, I was pointed towards a presentation by Professor Dan Gilbert on happiness (on Ted.com) and a book called "How Children Learn" by John Holt. Dan Gilbert stated we are reluctant to learn from the experience of others. Holt stated chilfren are natural learners, and will learn more if we let them explore their worlds.

Could we incorporate their ideas into the ways that Help (or User Assistance) is delivered and provide a better solution?
Should we could get users to access user assistance information before they get stuck, or will users always try to muddle through?
Can we make content more imaginative, and would that help?