Windows of Opportunity: Guidelines for Tricky Childhood Transitions

My 1-year-old son, Ben, won't drink from a sippy cup, and I have only myself to blame. With two older kids distracting me, I simply forgot to introduce it between 7 and 9 months, when doctors say babies are most willing to make this transition. Now he pushes his sippy away every time I offer it, no matter how thirsty he is.

Luckily, Ben has learned to drink from a straw. But his extreme stubbornness highlights the importance of finding that "magic window" for every kid transition, from saying bye-bye to the Binky to removing a bike's training wheels. So mark your calendar -- we've gotten the word from experts about the ideal time to do almost everything.

Magic Window: 2 to 4 Weeks Letting your newborn drink from a bottle while she's first getting the hang of nursing could confuse her and might even make her reject your nipple. But most pediatricians agree that you should introduce bottle-feeding before she's 1 month old. "If you wait any longer than that, your baby may not want it," says Tanya Remer Altmann, M.D., a pediatrician and author of Mommy Calls. Anyway, it'll be nice to let your partner handle a feeding.

Smart Strategy If you plan to pump regularly, you should rent or buy an electric one that works both breasts simultaneously to save time. Use it after you nurse your child in the morning, when your supply is probably at its peak. And make sure you leave the room when Dad or Grandma does that first bottle-feeding, since your baby might resist taking a bottle if she sees you're nearby.

Magic Window: 4 to 6 Months By this age, most babies don't need a middle-of-the-night feeding and are capable of putting themselves back to sleep. Your child may do it on his own if you keep to a regular evening routine. Otherwise, this is the time to sleep-train him, whether you have the stomach to let him cry it out or prefer soothing him every five minutes and gradually increasing the interval between visits. "If you wait until around 8 months he'll remember that you used to come in on demand, which will make him more persistent," says Dr. Altmann.

Smart Strategy If you're not having luck getting him to doze off on his own, put him down earlier, before he gets fussy and overtired. You can also buy a white-noise machine and room-darkening shades to block out the sound and light that may be disturbing your child's ability to fall -- and stay -- asleep.

Magic Window: 7 to 9 Months Your baby probably won't be able to drink out of it right away, but you should place a two-handled cup on his high-chair tray during every meal anyway. With practice and encouragement, he'll figure out how to drink from it, and that will make weaning from the bottle a simpler task.

Smart Strategy If your little one is having trouble using a sippy, try removing the spill-proof valve. "It may make a mess, but it's a lot easier for a child to drink the liquid that way and switch to a regular cup later on," says Julie Lumeng, M.D., a developmental-behavioral pediatrician at the University of Michigan, in Ann Arbor. Put formula or breast milk in the sippy, not just water, so your baby will become comfortable drinking them from a cup once he's weaned.

Magic Window: Around 6 Months Though your mom may have given you cereal in your bottle as a newborn, your child could gag on the thicker consistency and might be more susceptible to food allergies from this early exposure. Wait until she's close to 6 months old, and look for these cues that she's ready for solids: She sits upright with help, has good head control, puts things in her mouth, and seems interested in what you're eating. Don't wait longer than 6 months, because your baby needs the iron in baby cereal as well as the extra calories from food.

Smart Strategy Introduce solids later in the day, when your milk supply is lower. "Find that time when your baby has finished breastfeeding but is still looking around for more," suggests Marianne Neifert, M.D., a pediatrician and the author of Great Expectations: The Essential Guide to Breastfeeding.

Magic Window: 12 to 18 Months At this age, many babies naturally gravitate toward a soft blanket, a stuffed animal, or a doll. You can help turn an object into a lovey by snuggling it against her when you read together or when your child is napping. Separation anxiety typically peaks early in the second year, and having a comfort object in hand will help reassure your child when she's not near you. (About 40 percent of children never become attached to a comfort object, so don't worry if your kid doesn't.)

Smart Strategy Losing a lovey can be devastating for a child. So you may want to get some identical backups and switch them out once she chooses one so they both get that soothing "used" feeling.

Magic Window: 12 to 23 Months Your baby's beloved Binky satisfies his urge to suck and reduces his risk of SIDS. But once he's toddling around, it can affect his ability to interact with others and be an obstacle in his speech development. Start limiting pacifier use to nighttime and stressful moments (such as when you're leaving him with a sitter) by age 1, and stop it altogether by age 2. "After that the paci becomes a habit that's very hard to break," says Dr. Altmann.

Smart Strategy Leave his pacifiers for the "Binky fairy," who will take them away and bring a toy in their place. Or have a pacifier going-away party -- put them all in a box he can help decorate, sing some goodbye songs, and then get rid of them for good.

Magic Window: 2 1/2 to 3 Years Just because your 2-year-old can climb out of her crib doesn't mean she's ready for a big-kid bed. Instead use a crib tent, a domed mesh canopy that will prevent your child from getting out -- but that she'll probably think is fun. Once she seems cramped, switch her to a toddler bed or a standard twin with bed rails.

Smart Strategy A few weeks before the move, point out the big-kid bed an older sibling or her friend uses. Get her excited by letting her pick out some fun sheets. If she seems nervous or resistant, have her try napping in her new digs at first, then transition her to a nighttime stay in a week or so.

Magic Window: 2 1/2 to 3 Years Sure, some kids use the toilet earlier. But a study published in Pediatrics found that parents who start the process before their child is 27 months old end up dealing with soggy underwear for longer than those who wait for this window. "If you do it too early, you can end up spending months training her," says Dr. Altmann. "But by waiting, you might be able to do it in a weekend."

Smart Strategy It's fine to give your toddler a potty to get her excited. Keep in mind, though, that just because your child pees in it on occasion doesn't mean she's prepared to train. First, she needs to stay dry for several hours at a time, have words to describe each act (such as "pee" and "poop"), and be able to pull her pants up and down and get on and off the potty by herself. "You should also assess her level of cooperation," says Edward Christophersen, Ph.D., a Kansas City, Missouri, potty-training expert and author of Parenting That Works. "If you ask your child to do something and she starts to run away, you should wait a while to potty train her."

Magic Window: 3 to 5 Years Naps are tricky, so pay close attention to your child's cues. While 92 percent of 3-year-olds take an afternoon snooze, less than half of 4-year-olds do -- and most kids drop it entirely by kindergarten. If your child falls asleep quickly when you put him down in the afternoon, he still needs a nap, says Marc Weissbluth, M.D., a pediatrician and author of Healthy Sleep Habits, Happy Child. But if after napping he can't wind down till 9:30 p.m., it's time to say adios to his siesta.

Smart Strategy When your child first stops napping, move his bedtime up 30 to 60 minutes. Also keep giving him quiet time in the afternoon (or ask his child-care center or preschool to do so). This will give you both a much-needed break -- and grant him the freedom to nod off on days he's particularly tired.

Magic Window: 5 to 7 Years Most kids can ride a two-wheeler by kindergarten, says Rich Conroy, director of bicycle-education programs for Bike New York, a New York City nonprofit. Get your child a bike with training wheels, and let him practice until he peddles around the nabe like a pro.

Smart Strategy Take off the training wheels and the pedals (make sure your child can place his feet flat on the ground while sitting on the seat). Tell him to push the bike forward with his legs and lift his feet off the ground. Once he masters the balance, put the pedals back on and watch him go.

Magic Window: 6 to 7 Years Kids younger than this need supervision, as they could slip and fall, says Dr. Altmann. Before you let your kid bathe or take a shower solo, watch her a few times to make sure she washes her body and shampoos her hair thoroughly, gets all the suds out, and turns the shower on and off -- without flooding the bathroom.

Smart Strategy Get your child comfortable with the idea when she's a preschooler. Use the sprayer to rinse her hair, and then let her try it. Also invite her to shower with you as an occasional treat (boys should do this with Dad). "It can be a little scary for kids to have water rushing at their head," Dr. Altmann says, "but if you start young, they'll be used it."

If you miss your window, are you doomed? No way. With these tactics, you can help your child reach the next level.

Take a break. When you get frustrated your child senses it, which only intensifies the situation. So if he resists learning a new skill, take a deep breath and let it go. You can always try again in a month or so.

Put the decision in her hands. Give your child choices whenever possible ("Do you want to sit on the big potty or the little one?") to encourage cooperation

Be consistent. Once you take the paci away, don't bring it back -- no matter how embarrassed you are about your child's public crying jag. Reneging on your word after you've set a limit undermines your authority.

Use modeling to your advantage. Seeing a friend do something can inspire your child. When her pal switches to a toddler bed, point out what a big girl she is.

Originally published in the February 2011 issue of Parents magazine.