Urban gaming simulation (UGS) appeared in American universities in the early 1960s, following the successful applications of gaming simulations in military and financial fields, when urban structures were in crisis. This guest column, by a philosopher who has speculated about philosophy and other cultural endeavors as forms of play, points out conceptual traps that specialists in UGS should avoid and decisions they ought to consider making. In particular, the author warns against making too much of the distinction between “games” and “play” and advises UGS practitioners to conceive of their own activity as playful and exploratory. He argues that practitioners should approach clients not as “professionals” but rather as people with experience acquired from much play, on many different terrains. The essay concludes by suggesting that professionals in all fields—scientific and otherwise—ought to see themselves in much the same way.