If you have done the pre-work in helping your child imagine what a day in the life at the new preschool will be, the first day should be much easier. The key on this day is to be as relaxed and as positive as you can be. Your child will be keying his emotions off of yours.
Leave yourself lots of time to get ready and to get to school. Be sure to build in an extra “toddler” cushion that allows for relaxed breakfast eating and dressing. Also, leave enough time to get to preschool without rushing. This is not the day to get into a power struggle over the Dora versus Mickey Mouse cup. Let your child have her way this morning and try to avoid typical toddler confrontations.
Pack a little “lovie” and a picture of your family. Put something in his/her backpack that is a comfort item from home (stuffed animal, favorite car, etc.) and let the preschool teacher know that it is in there should tears appear. Same with the photo.
Smile. Again, your wee one is really keying off of your emotions and all of it needs to be remarkably positive, even as you are peeling him/her off of you. If you need to wear sunglasses (I did), do! And hold your tears as best you can for when you get out to your car. It is also extremely important for your child to see you being warm and welcoming to her new teacher(s). Again, if you seem to trust the teacher your child is more likely to as well.
– Our Friends at SavvySource.com
Starting School: Preparing for the Big Day
Starting School: The First Few Weeks