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Preparation and planning, plus plenty of TLC, will help ease your child's transition from preschool (or no school) to the big-kid responsibilities of kindergarten.
Three weeks before school
Visit the school. Starting kindergarten means more than just new faces and new routines — it also means spending the better part of the day in an unfamiliar (and possibly scary) place. Ease the transition by visiting the school together now. Spend some time at the playground so your soon-to-be-kindergartner can start to feel at home. If the school building is open, give him an informal tour, sitting down in the lunchroom (bring a banana or something else to snack on) and looking at the library and gymnasium. Don't forget to point out the bathrooms and maybe even stage a dry run. If you know which classroom your child will be in, stop by and show him the cubbies where he'll keep his things. (If not, just visit a sample kindergarten classroom.) If the walls are still bare and chairs are stacked on tables, be sure to explain that on the first day of school the walls will be decorated with colorful pictures and learning materials and the chairs will be grouped around activity tables.
Read books about school together. A great way to ease new-school jitters is to read a book about going to kindergarten. Books worth checking out include Annabelle Swift, Kindergartner by Amy Schwartz, Back to School for Rotten Ralph by Jack Gantos and Nicole Rubel, and Miss Bindergarten Gets Ready for Kindergarten by Joseph Slate. These books not only show how other kids have overcome school worries, they also give your child an opening to talk about his own fears. At this point, keep your discussions about school pretty general; you don't want to overwhelm your kindergartner with a lot of details that may worry him even more. Let him set the pace and the agenda — answer his questions but don't give him a lot of information that he doesn't want or isn't ready to absorb.
Plan playdates. Get a class list (or at least a few names and numbers) from the school principal, and arrange a couple of playdates so your kindergartner can get to know his new classmates. Some schools sponsor picnics or potlucks for incoming students and their parents; if yours doesn't, consider organizing your own potluck or pizza party on the school playground (with permission) or at a nearby park.
Two weeks before school
Take a clothing inventory. Before the final rush to get everything ready for the new school year, check your child's wardrobe to see what still fits, what works for school, and which new fall clothes he'll need. When you have a detailed list, take him shopping so he can pick out one or two special pieces of clothing, a few new caps or socks, and, of course, some new school shoes or sneakers. Sometimes new things act as talismans — good-luck charms that help a child get through something foreign and scary, like the first day of school.
Write a letter to the teacher. If you know who your child's teacher will be, consider helping him write a letter introducing himself. He can tell the teacher about some of his favorite activities and books, and perhaps include details about what he did this summer. Writing a letter is also a great way to tell the teacher your child's nickname, if he has one; that way, she can put it on your child's cubby to help him feel at home. Ask your child whether he wants to add some personal artwork and have him sign his name at the bottom.
One week before school
Get organized. Clean out and organize your child's closet and dresser drawers so that he has all his school clothing options at his fingertips. Make sure he understands which are his school clothes, so he can choose his own outfits on school days.
Buy back-to-school gear. Now's the time to fill in school-gear gaps — including a backpack, a lunchbox, and miscellaneous school supplies. Check out your child's choices before you plunk down your cash — after all, you're the one who'll be packing his lunchbox and backpack every morning. You need to know that the lunchbox latch is easy for him to open, for instance, and that the backpack zipper won't snag every time he closes it. While you're at it, let your kindergartner pick out some pencils, drawing pads, and art supplies to help him get into the school spirit.
Talk about what to expect. You've probably already talked about all the fun things your child will do in kindergarten, and you may even have visited the school. Now's the time to go over the class routine in as much detail as you can. Give him an idea of the daily schedule, and talk to him about what will be new and what may be familiar from his preschool days (such as rest time, circle time, and story time).
Ease into the school-year schedule. Though it's still light out until fairly late, start following school-year rules now: dinner at 6 p.m., bath at 7, reading time, then lights out at 8 (or whatever bedtime you choose). If your child's been outside riding his bike until dusk every night this summer, change his schedule gradually, making each activity (dinner, bath, bedtime) 20 or 30 minutes earlier each day, until he's used to the new evening routine.
Begin the morning routine. When the first day of school arrives, it'll be a lot easier if everyone knows the morning drill. Together with your child, make a list of what he needs to do in time to catch the school bus or make it to class by the first bell: brush teeth, wash face, get dressed, eat breakfast, put on shoes, and so on. If he isn't reading yet, create a colorful picture-list depicting the morning routine, either by drawing pictures together or by cutting out magazine photos illustrating the various activities, and put it up in his room so he can refer to it each morning.
Meet the teacher. Since teachers are now preparing their classrooms and getting ready for the school year, it's a great time to stop by to say hello. Many kindergarten teachers appreciate the opportunity to sit down one-on-one with new students and spend a few minutes getting to know them. (If your child's teacher is too busy to stop and talk, ask if you might come back another time.) As a bonus, the classroom will be shaping up and it won't look as empty and impersonal as it might have when you visited before. While your child is exploring, you can quietly discuss with the teacher any special concerns you have — if he's shy, for instance, or has any special needs. Also let the teacher know about friends your child may already have in class, so she's sure to pair them up during those first awkward days.
Rehearse the route. Practice the route your child will take to school, either by walking it together or driving; if he'll be riding the school bus, drive the bus route. Show your child how he'll enter the school and exactly how to find his classroom, reminding him that people will be there to help him every step of the way.
The night before school
Practice your goodbyes. Talk to your child about what the two of you will say and do when it's time to bid farewell. Use any special code words or actions that you have, agree on the number of kisses and hugs that will be required, and even decide whether you should say "See you later" or "I have to go now." Giving your child the job of pushing you out of the room (or down the street, if he's getting on the bus) literally puts control of the parting in his hands. Then, when the time comes, make your goodbye short, sweet, and casual. If you want the option of sticking around during the first few days of school, check with the teacher before you make any promises. Most kindergarten teachers prefer that parents leave as soon as possible. If your child's teacher says it's okay to stay, then you have the tougher decision of whether to exercise this option. For some kindergartners, having a parent nearby provides the security they need to get into the swing of things. But for others, Mommy or Daddy's extended presence only postpones the inevitable pain of saying goodbye, and it can send a message you don't want to send: Being at school without us is scary, and we're not sure you can handle it. Having a plan for this momentous parting will by no means guarantee a breezy goodbye, but it may help make it easier for both of you.
Choose first-day clothes. Lay out the outfit he chooses (try to stay out of the choosing process), with maybe a cool- and a warm-weather option, since September weather can be iffy. In fact, getting your child into the laying-out-clothes habit helps eliminate a decision and a fair amount of angst during the morning rush hour. This way, if his favorite jeans aren't clean, you'll know at 7 p.m. instead of 7 a.m.
Pre-pack the backpack. Together with your child, pre-pack as much as possible to ease the morning frenzy. If he'll bring a lunch, prepare it now and store it in the fridge. As a surprise, sneak in a special object, a family photo, or a love note that will tell your child you're thinking about him. Also consider a special treat. It may not be at the top of the healthy list — but if there's any day to relax the rules, this is it (be sure to check the school's food policy first, since many discourage sugary and fatty snacks).
Give a gift. Consider giving your child a token that symbolizes the specialness of starting kindergarten. It could be a new book, inscribed with the date and the name of the school and class he's entering, a child's wallet with family pictures inside, or even something as utilitarian as an alarm clock to help him adjust to his new schedule.
The big day
Take the day off. If you can swing it, take the day off work (or arrange to go in late and leave early). This way, you can spend a little extra time at drop-off or give your child a grand bus-stop sendoff, be there when he gets out (even if he'll normally stay in after-school care or go home with a babysitter), and perhaps even treat him to a celebratory milkshake to mark the day. Eliminating your own morning and after-work crunch will make it easier to help your child through his, and he'll get the message that this is, indeed, a special day.
Hold the cornflakes. There will be plenty of rushed cold-cereal and instant-oatmeal breakfasts during the course of the school year. Today, get up early and make a special morning meal, like pancakes in the shape of a school bus or your child's all-time favorite breakfast food. Take the time to eat together as a family, too, so you can discuss the exciting day ahead.
Take a first-day photo. Don't forget to snap a shot of your child with his first-day-of-school outfit (or school uniform) and backpack on, to document this important milestone. Some families have their child hold a sign with the date or grade each year. Others shoot the picture in the same spot year after year (in front of a tree, for example) to emphasize how much their child has grown.
Allow for crying time. After your child is safely deposited in his classroom or on the bus, then, and only then, can you let those bittersweet tears flow. You are now the parent of a kindergartner, and it's natural to have mixed feelings about that. Just don't cry in front of your child — after all, it's hard enough being a kid without having to worry about your parents, too.
Before you shop for school supplies, see our guide to gearing up for kindergarten.