Google Now tries to anticipate the user, I think, but it does a very poor job of it. The occasional airport alerts are usually accurate, but even though it has enough information to accurately predict my commute, and even though it knows I can take multiple routes to work, it never ever tells me proactively "hey, there's an accident farther down on your usual route and things are snarled up; consider an alternate route today". By the time I have the information through conventional means (observation), it's too late to adjust.

I want my applications to behave like excellent executive assistants: they wait for orders and then handle what I told them to for me. I want to be able to express specific things precisely at a higher level of abstraction, and have the app take it from there.

Yes, this. Why the heck is this so hard? (Or, put another way, unprofitable?)