Julie Masino stepped down as Cracker Barrel’s CEO at the end of July, a little over a year after a logo redesign turned into a $100 million lesson in reading your customer wrong. Her words on the way out: “I feel like I’ve been fired by America.” The internet mostly treated it as a punchline. I didn’t laugh. I recognized it.
At 26, I left an ad agency job in New York to run a bourbon brand for a client in Louisville, Kentucky. Bigger title, bigger paycheck, and — I was sure — a chance to finally do the work right. The brand’s drinkers were mostly Southern, mostly loyal to it for reasons that had nothing to do with me. I was positive they were dying for my creative direction. I was going to sharpen the brand, modernize the image, turn it from hick to hip.

