Set aside some time to talk to your child about his day. Your kindergartner may be fighting sleep simply because he needs time to check in with you after a long day at school. Especially if you work long hours yourself, allot some time before bed to chat with him about goings-on at kindergarten and to get the scoop on the latest dramas in his social life. You may find that he's more amenable to sleep if he's had a chance to unburden himself.
Stick to a bedtime routine. Make a pictorial chart for your kindergartner to follow — including his bath, toothbrushing, bedtime story, and goodnight kiss. Also include his usual (and reasonable) requests — like that second sip of water or a peek at the moon. Give him some notice before it's time to start the routine each night ("Austin, five minutes before bath time!"). Try not to let him dawdle or drag things out with activities that aren't part of the routine — no third glass of water or round of "Dinosaur Rock," for instance.
Motivate him. When your kindergartner goes to bed on time, the rewards for you are obvious. Make it clear what's in it for him too. The morning after he sticks with the routine, praise him and give him a sticker to put on a special chart. Offer him a reward — like a new book or a bike ride — when he stays in bed four or five nights in a row. (Start small — for a kindergartner, a few days is a long time to hang in there!) Try to tune in to your child's particular motivators: "When you're big enough to stay in bed all night, you can spend the night at Grandma's." You might even set up a bartering system — tokens earned for getting to bed on time and staying there, and tokens lost for getting to bed late or sneaking out. A certain number of tokens "buys" him game time on the computer, a trip to the park with you, or a sleepover with his buddies. (Just what you need: Three wakeful kindergartners!)
Offer choices. Refusing to go to bed is a powerful way for your child to assert himself. So it might help to find an acceptable means for allowing him to be assertive. Let him decide if he wants to hear Shel Silverstein poems or a chapter of Stuart Little before lights-out, for instance, or ask if he'd like a sip of water before or after he climbs into bed. Be careful to offer only choices you can live with; if you ask "Want to go to bed now?" you probably won't like the answer you get.
Be calm but firm. Even if your 5-year-old cries or pleads for an exception to the going-to-bed rule, stand your ground. If you're frustrated, don't engage in a power struggle. Speak calmly and quietly but insist that when time's up, time's up. If you give in to his request for "five more minutes, please," you'll only hear it again tomorrow night.
Take a stepladder to success. You can't expect your child to learn, in one fell swoop, how to go to bed and sleep all night according to your perfect scenario. Take it one step at a time: If your kindergartner's used to falling asleep in your bed, maybe his first step is to fall asleep in his own. His second step could be learning to limit his nocturnal "escapes" to one per night, or calling for you only once without actually getting up. Build your way to the ultimate goal (sleeping through the night without a peep) in successive, successful steps.
Problem solve. Figure out why your 5-year-old finds it tough to keep his head on the pillow at night. Ask about his specific objections to bedtime — is it because he's not tired? Scared? It's too quiet? Offer him a flashlight if he's afraid of the dark. Eliminate nighttime TV if the shows make him jumpy. Let him play a soothing CD at low volume if the quiet is too much for him. And be sure to listen to his ideas about what might be helpful. After all, a plan that he helps devise has a better chance of succeeding. Make sure your kindergartner's getting lots of fresh air and exercise during the day. Or consider moving bedtime back an hour (just make sure to allow for 9 1/2 to 11 1/2 hours of sleep a night, which is what kids this age need). Some physical activity and a slight schedule change may be all it takes to ensure that your child is good and tired when bedtime rolls around.