A new class of online services allows internet media sites to direct users from articles they are currently reading to other content they may be interested in. This process creates a “browsing path” along which there is potential for repeated interaction between the user and the provider, giving rise to a dynamic optimization problem. A key metric that often underlies this recommendation process is the click-through rate (CTR) of candidate articles. While CTR is a measure of instantaneous click likelihood, we analyze the performance improvement that one may achieve by some lookahead that accounts for the potential future path of users. To that end, using a large data set of user path history at major media sites, we introduce and derive a representation of content along two key dimensions: clickability, the likelihood to click to an article when it is recommended; and engageability, the likelihood to click from an article when it hosts a recommendation. We then propose a class of heuristics that leverage both clickability and engageability, and provide theoretical support for favoring such path-focused heuristics over myopic heuristics that focus only on clickability (no lookahead). We conduct a live pilot experiment that measures the performance of a practical proxy of our proposed class, when integrated into the operating system of a worldwide leading provider of content recommendations. We estimate the aggregate improvement in clicks-per-visit relative to the CTR-driven current practice. The documented improvement highlights the importance and the practicality of efficiently incorporating for the future path of users in real time.