A long time ago I did some work for a bakery that had been on the market for a few years.
They wanted to change the appearance of the labels they stuck on the packaged goods - cookies, crackers, pound cakes and the like. New laws required that a lot more information about the product be featured on the label. Unfortunately, the size of the stickers themselves remained the same but the bakery still wanted to keep the images that didn't convey any information. That was understandable, but it posed a real challenge because I had to fit in a lot of new text in such a way that the whole thing didn't look cramped or tacky.
I did a bunch of brainstorming and ended up with four very different looks to make sure the management would like at least one of them. I was proud of how efficiently I was able to display the information while keeping it looking good.
I took the proofs to the client, and he went from being impressed to angry and panicked.
Client: WHERE are my barcodes?
Note one: There was never a mention about any barcodes while we had been discussing the job.
Note two: Having barcodes on labels at that time was still only optional.
Note three: they didn't already have barcodes, and seemed to expect us to design them... in Photoshop.
Note four: The customer was my dad.