What do we mean when we say it today?
This phrase is really just used to say, "Hey, I was in a better place before. Right now pretty much stinks in comparison." but with more grace and poise. We use it in the same way as Duke Senior does here. He's really kind to Orlando (even though he's being totally rude) because he gets it—he knows that sometimes life sucks. But he's willing to be positive anyway.
We've all met those people. Most of us strive to be those people. It takes tact, grace, and a whole lotta optimism to state it this way without whining.