Even though your son might be the one in tears, saying goodbye is often harder on you than your child! One way to make goodbyes easier is to make sure your son is busy with an activity that he enjoys before you have to leave. When it is time for you to go, keep your goodbye short and sweet with a few reassuring words and a cheerful wave good-bye (prolonging the goodbye will only make it more upsetting for both of you). At first, your son will likely still be upset when you leave, but over time goodbyes will become easier. It might be helpful to try leaving your son for small periods of time at first, and then slowly increasing the time you are away. There is a great episode of Daniel Tiger’s Neighborhood called “Daniel’s Babysitter/ Daniel Goes to School” that your son might enjoy. The episode is about dealing with separation and teaches children that “grown-ups always come back” (you can watch it free online at pbs.org).