M.D.
Oh yes...my son has major separation anxiety and he is almost 4. (I am also a very anxious and sensitive person by nature). I was his only "playmate" for much of his young life and preschool was his first real intro to groups of children as well as lengthy periods of time away from me. I have had him in gymnastics, soccer, basketball, library classes, etc....but I have always been there watching or actually participating with him. I think the biggest shock for my son was the amount of time I was away from him. These are things that we are working on right now - hopefully some can work for you too? (1) Consistency - he will need the same facility, the same teachers, the same group of children for a good period of time to feel safe. (2) Duration -we initially did 1 Friday a week and I have been advised to bump it up to two or more times a week. I was told that they work through their anxiety faster this way, they get more familiar with the children and teachers more quickly and it is not so hard on them if they miss a day due to illness, etc. (3) Playdates with other children in the class. Playdates allow them to get to know others in the class more quickly and provides a greater level of comfort in the classroom. (4) Bringing comfort items from home for show and tell if it is offered in the classroom. It helps to have something familiar in the class if they need it. (5) Children turning 3 hit a developmental milestone where they become aware of death. They need a lot of reassurance that when you are gone, you are coming back. Make sure you never leave the room without telling your son. Make sure you are on time to pick him up (it sounds like you already have this down). (6) Eliminate any stress at home if there is any and don't let him watch scary movies (especially movies that involve death, such as Bambi, etc.) (7) Let your son "practice" separations in a less stressful environment. For example, we have never used a babysitter for our son. We are working on having a babysitter at our house while we are home for a bit, then transitioning to short periods of time away, then longer outings. Sometimes separation anxiety is a two way street, and I have come to realize that I need to let go in order for him to feel comfortable letting go as well. (8) There are some great articles out there to read. The one that helped me most was from Sesame Street but I can't find it any more. This one is pretty good though:
http://www.parenting-ed.org/handout3/Specific%20Concerns%...
Oh...and I learned this one the hard way. DON'T stay in the class with him! It is ok to check out the curriculum one day and sit with him...so you know how the schedule goes and you are aware of the temperaments of the different kids he plays with. The next time, you both will suffer and cry during the separation. After that it gets easier each time. By staying in the class the whole time I was essentially signaling to my son that I didn't think it was a safe place and that I should stay with him to protect him. Staying there with him does not allow him the opportunity to bond with the teacher and other students. The next time I cried in utter horror as I heard him banging on the door behind me as I left screaming "mommy...COME GET ME!!!" I stayed in the library down the hall from his classroom and listened to this go on for about 30 minutes. I felt physically ill and wanted to go grab him out of the room. The next time I explained that I would come get him after circle time (their last activity of the day, as he doesn't understand how to tell time yet). He cried for 5 minutes, and as I walked down the hall the crying stopped. I have found that he cries during the time I am in the classroom, and it stops when I am gone. You would think that children would be comforted to have you there with them, but it actually causes more anxiety. If you trust the caregivers and are comfortable with the other children there...then the best thing you can do for him is drop him off and go.
It will be hard, mama...but so worth it for your son in the long run.