Finding Hope

I have wrestled a lot lately with the word hope.
The dictionary says that hope means 
to cherish a desire with anticipation
to desire with expectation of obtainment
to expect with confidence : TRUST

Recently I have claimed that through hardship and "mid-life crisis" points, Hope {and Truth} will prevail...
What does that really mean?
What desire am I cherishing with anticipation?
What am I expecting?
Do I expect with confidence--do I TRUST?

To have hope in an idea or a belief system seems more and more difficult for me.
There seems to be too many variables that obstruct the purity of what I once thought it was.
It's messy and blurry and I want to run away from figuring out what it means to me...

...Then Obama won the election and in his acceptance speech he said this:

I have always believed that hope is that stubborn thing inside us that insists, despite all the evidence to the contrary, that something better awaits us so long as we have the courage to keep reaching, to keep working, to keep fighting.-- Barack Obama

Obama fan or not, these are pretty powerful words.

 They have begun to challenge me to face the skepticism I have surrounding what 
hope really is.

So now my question is becoming: 

Do I have enough courage to keep reaching, working and fighting?

I hope so.