IN AUGUST 2014, I LOST my freelancing job as the Director of Content at Grey, a global, hundred-year-old advertising agency, often referenced in Mad Men. It’s where Duck Phillips landed after being dumped by Sterling Cooper. Because Grey slashed my short-lived position, a frequent mini-tragedy at ad agencies, I was searching for a new full-time gig. I became obsessed with joining one of the bright, shiny digital media start-ups in New York City, partly out of fear that if I didn’t work at a hot tech-based company, I would soon become a dinosaur. I had studied journalism, and traditional media were on life support. As a Gen Xer, I ...

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