This article uses privileged families who hire Independent Educational Consultants (IECs) as an instance to examine how privileged parents collaborate with individuals whom they consider educational experts to support their children in the college race. We argue that advantaged parents' anxieties about their children have created a market for IECs who provide expert advice in order to mitigate the uncertainties that these parents experience and to manage various goals that they want to achieve at an important turning point in their children's lives. Drawing primarily on interviews with parents who work with IECs, we introduce the concept of “collaborative cultivation” to analyze the processes whereby advantaged parents rely on the expertise and expert status of private counselors to cope with their and their children's vulnerability in the college race while at the same time preparing their children for the unknown future. The parental method of “concerted cultivation” reveals how elite parents rely on individuals they perceive as experts to establish “bridges” between their own social worlds and the academic worlds that appear to beyond their control. This bridging labor points to the myriad cultural beliefs enacted to justify the child‐rearing goals that privileged parents wish to accomplish by working with IECs.