It's a very nice quote but Shakespeare never actually said this, it's a common misquotation. There are many sayings that are wrongly attributed to Shakespeare, this is one of them...
The actual quote is
"Oft expectation fails, and most oft there
Where most it promises; and oft it hits
Where hope is coldest, and despair most fits."
It's from 'All's Well That Ends Well'
It means that often when you have high expectations, they fail. And often when things seem the bleakest is when something good happens.
Source: Google
I actually posted this quote couple of pages ago, so I know
Otherwise I am neither a Shakespeare aficionado nor an expert
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