Establish bedtime rituals. Whether in school or at home, children benefit from having a routine. Set up a schedule, designating a specific bedtime. For example, after supper, homework and play, you could help your child straighten up his room. While he takes a bath, you can turn down the covers and plug in a night light, creating a comfortable and secure atmosphere.
Allow your child to have input in the process. Your kindergartener will probably be much more amenable to sleeping by himself if he is allowed to have some options. For example, tell your child he can pick a favorite stuffed animal or other toy for company while falling asleep. If your child asks to watch television or listen to the radio, compromise by playing some soft music or lullabies in the room at a low volume. This may help him overcome feelings of loneliness.
Transition into sleeping independence. If your child is frightened to sleep in his own room, allow him to sleep on a pallet on the floor of your bedroom. After your child begins school, talk to her about the importance of getting a lot of sleep so she will make good grades and have energy to participate in all the fun activities. Then make the move to the bedroom, but tell your child you will check in on her in awhile.
Accept and praise gradual progress. There may be frustrating moments, but focus on overall success. After your child spends his first night in the bed by himself, make a big deal out of it the next morning by bragging on them and encouraging them to continue. Get other family members to praise your kindergartener too. Positive reinforcement can work wonders.