Ben Polak has made four rolls of the die, circumnavigated the board once, and he’s already lost 75 dollars. This game theorist has convinced me that it’s going to take more than game prowess to win at life. And we’re just playing Monopoly. It’s four o’clock on a Thursday and the advent of the weekend has us taking a break around the familiar Milton Bradley board, though Uncle Pennybags has succumbed to the Big Apple’s call: this isn’t just Monopoly, this is Times Square Monopoly.

Polak’s first roll takes him a short five spaces to Income Tax and within seconds he’s lost 10% of his assets. A professor of game theory, the study of strategic interactions between parties, Polak is quick to deny having any real skills in board games. He cites afternoons playing Snap (“really, the easiest game in the world”) with his four-year-old as his only game outlet. I’m beginning to believe his self-deprecation, but perhaps feigning ignorance is just a game theorist’s way of beguiling me into going easy. We’ll see. It’s on.

Hailing from Portsmouth, England, Polak majored in economics at Cambridge. “Game theory wasn’t around at all when I was an undergraduate,” he recalls, “there was one professor who told me this was an interesting new field.” His undergraduate exposure to the subject thus came mainly through one-on-one mentorship, but when Polak came to the United States to earn his Ph.D at Harvard, he suddenly found an abundance of game theory courses. His next step brought him to Yale, where “they were kind enough to hire me.”

Game theory is a varied field, and as I want to know my opponent, I ask about his work. He deflects by saying, “I tend to be interested in everything. That’s the problem.” Excited by both its practical and theoretical aspects, Polak admits, “I’m a typical academic nerd, so it doesn’t take a lot to get me interested.”

Another roll, an eight-space journey, and Polak’s luck is no better. A purchase from just seconds before has him shelling out a pastel $32. Despite his poor showing thus far, Polak maintains that it is possible to use game theory in board games. With economist friends in Australia, where apparently the people are “much more competitive,” Polak did just that. The game they dissected wasn’t Monopoly, however, but another Milton Bradley favorite: The Game of Life. “It’s actually a pretty complicated game,” muses Polak. Yale students beware: one of the most compelling aspects of the game is the decision to go to college. “College raises the value of your future life, but at what cost of foregone salary?” considers Polak. He seems ready to make a conclusion, but is distracted when he lands on Free Parking. I cross my fingers on the superiority of the first option.

Game theorist or not, everyone automatically considers strategic interactions between parties. Take the above choice about attending college: we all had to consider how a degree would raise our relative worth against the cost we’d incur. And every time we consider how the actions of other people may affect us, we are acting as game theorists. We do it when we choose to buy presents in order to receive them, or decide the optimal time to vote off the strongest player on The Weakest Link, or use real-world economic theory to describe competition between firms, a fluctuating stock-market, and a mortgage crisis.

Treating life like a game can help us make huge decisions, eliminate competition, and earn us thousands of dollars: why can’t we call games our blueprint for life? Wouldn’t it be great to reduce all our anxieties and issues to a few simple rolls? But here’s how life and games differ according to Polak: in games, “it doesn’t matter if you’re second or third or fourth, you only win it if you’re first.” Luckily, in life, it’s okay to come in second once in a while.

When I ask how I can use game theory to see my world differently, though, (“How do economists approach life differently?”), Polak simply shrugs and says that they’re “likely to spend less time choosing between alternatives that are practically identical.” Which means he can admit that he never knows if his wife would like flowers, a necklace, or a book for her birthday, so stressing about it really doesn’t make a difference. Besides, as a self-proclaimed “anxious” and “manic” person, Polak has enough to consider at the moment: he’s two properties and $150 down, and time’s running out.

The game is Monopoly, though, which means we could play all night and still not finish. In the end, Ben Polak cuts his losses, shrugs on his jacket, and departs, leaving me to wonder whether I can use Monopoly as a gauge of future success.