When Optimization Is a Trap

Max Hawkins had started to feel trapped by his optimized life. Every weekday, he woke up at exactly 7 a.m. and grabbed a single-­origin pour-­over from the best café in his San Francisco neighborhood, at least according to Yelp. He got on his bike and rode 15 minutes and 37 seconds along the best possible route to Google, where he was a software engineer. He spent eight hours working, then met friends for a beer at a craft brewery or a hang in Mission Dolores Park. But despite his great job and charmed life, something felt off.One afternoon at work, while reading an academic paper, he located the source of his ennui. The study, which tracked the movements of 100,000 anonymized mobile-phone users over six months, had found that human mobility is surprisingly predictable: Our days default to simple, repeatable patterns. The engineer part of Max’s brain thought the research was pretty cool, but he also found it unsettling. “There was something very programmed about the way I was living,” he told me. If his movements were that predictable, where did that leave his free will?That night, as he lay in bed, he started thinking about how the structure of people’s lives determines the outcomes of their lives. His life’s structure had become disconcertingly rigid. He didn’t like the sense that, day to day, he was reading a story he’d already read.The following Friday, Max and a friend were planning to hang out at a bar that had recently opened, one with all the qualities Max usually looked for: good beer, soft lighting, nostalgic indie hits on the playlist. But he couldn’t get the human-mobility study off his mind. The new hip bar is exactly where a computer would expect me to go, he thought. So he decided to design an algorithm to help him break from his routine.[Read: The tension that defines modern life]Max had long been fascinated by how to infuse randomness into his work. (In college, he had learned to make computer-generated art, and often tried to inject a sense of sere