I've unsuccessfully tried to understand to the concept of 'expectations'; whether or not to live by plans because plans all too commonly fail. But it isn't so much the idea of a plan that is problematic, but rather putting too much of your hope into them. Kind of like an insurance policy, so that when plans don't pan out as expected, your hopes don't go crashing down with them.
But life is not worth living without hope. Where's the motivation to go on if there isn't at least the illusion of a better place? And most times, hope guides us to places we never expected to be, places that we can look back and say made us better people. So the goal of getting to the initial destination is irrelevant, but rather the steps taken to get, well, wherever.
So where do we place 'hope'? I'd like to think we can place it in the overall assurance that things will work out, regardless if we recognize it or not. Or maybe finding an intricate balance between 'hope' and 'expectations' so that they can exist harmoniously for our own individual peace of mind. But things like hope shouldn't be over analyzed anyways. It's complexity wasn't meant for such petty things like 'logic' in the first place.