Few children have had the chance to travel alone anywhere, certainly not to the store or the playground. Few have the opportunity to get even a dash of street smarts: to practice getting themselves out of even a minor jam, to develop wayfinding skills, to navigate their neighborhood and choreograph their day--all valuable components of school readiness. Experienced kindergarten teachers see the fallout from this increasingly supervised life--with many incoming kindergartners more sophisticated than past cohorts, but also clingier and less sure of themselves. Some have visited Paris or Hawaii, but have not developed the skill to fall asleep on their own. Despite independent schools' cozy class sizes, devoted and well prepared teachers, and attunement to the best practices for separation, this distance from home and range of age and maturity (and immaturity) of fellow students can add to a student's sense of uncertainty. In this article, the author discusses some strategies schools can use to help parents help their children through the process of separation.