So how do you explain people like me who can differentiate "OMG the design is so 1995" vs "This pastel-colored theme looks rad!" but sucks when tasked to design it himself (end up with 1995 design).
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This is actually a very common stumbling block. See the Ira Glass video.. http://www.youtube.com/watch?v=PbC4gqZGPSY
You learn how to differentiate between good and bad much faster than you learn how to create good. Which can be super discouraging because it means that at first all it feels like is that you just keep realizing how bad you are and how much further you have to go.
Just keep practicing.