Undercover Mother

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As little ones enter the preschool or kindergarten stage, August no longer just means end of summer in terms of weather – it also means the start of the school year for most Chicago-area kids. Sending your little one off to school for the first time brews a strong blend of emotions. And while there may be little tinges of sadness infused in walking him or her through the door the first day, moms and dads can do a few things to help make the transition smooth:


About a month before school begins, start having small discussions about what the fall will bring school wise. When waking up the morning, for example, help your little one know that during the next few weeks, you’ll be practicing a little bit of a before-school routine after getting out of bed. Use this time to help your child adjust to getting ready for a day at school; consider it a good time, too, to monitor how much time little one needs to get ready and get out the door for a day of learning and fun. Take note of whether your little one seems grumpy or if he’s feeling rushed, as these feelings will carry over to the classroom. Make bedtime adjustments as necessary a few weeks before he or she actually has to leave the house for school.

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Once the school list comes out, fight the urge to run to Target alone to pick up school supplies. If it’s possible, arrange a special school shopping date with your child. During the date, pick out the school supplies on the list and talk about what each supply might be used for during the school year. This will help mentally prepare your little one for what’s to come while involving him in the process of getting ready for the school year. My oldest son loved picking out paper cups he and his classmates would use during snack time. He felt like he was contributing to the preparation, and as we picked out the items, he gained an idea of what he could expect from a morning at school.


If your child’s school offers an open house or meet and great before the first day, by all means, attend it together! Your little one will appreciate exploring his new classroom with his favorite trusted adults. Talk to the teacher together, and formally introduce your child to the teacher so he or she can see mom or dad interacting with the person who will be teaching, directing and guiding him or her every day. The interaction will also show your little one that the teacher is a new player in his life. Be sure to check out the bathroom, cubby hole or locker and circle time areas together, as these destinations will be frequented and should be familiar before your little one has to make a go at it alone.

Listen and Ask Questions

When talking about school or after attending an open house in the classroom, listen to your little one’s body language as well as comments. Often, as a parent, I find myself doing more than enough talking and explaining without taking the time needed to listen to what my little ones are thinking about situations. If your child hasn’t voiced many thoughts about school, try asking him or her some questions, like “What seems most exciting?” or “What are you most looking forward to doing at school?”

Street Sign

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Test Run

Before the first day of school begins, try walking to the bus stop together one morning and talking about what will probably happen during the morning commute. If you’ll be walking with or driving your child to school, consider taking a test run before the first day and actually arriving at your destination. Preschoolers and kindergartners appreciate knowing what lies ahead, and it may be comforting to do a mock morning routine and walk or ride to school before the first day actually arrives.


Ask your child if he or she would like to help label his or her school supplies, like a backpack, extra pair of clothes and classroom accessories. Again, it will help your little one share in the preparation for school and help your child familiarize with items that belong to him while at school. It will also save the teacher from pulling his or her hair out trying to discern whose Toy Story book bag belongs to who when said book bags get mixed up.

Collect and Share Information

Be sure to record or log into your phone the school’s phone number, address and the teacher’s email address. Also, decide on and bring your child’s emergency contacts before arriving the first day. Don’t forget to share with your little one who the school will call in the event you are unreachable during an emergency.

Hyacynth Worth writes about parenting, faith, marriage and living in a house filled with boys and high-levels of testosterone nearly daily at Undercover Mother. She attributes her oldest son’s back-to-school count down a direct result of the school supply shopping date. Bring on round two of the paper cup draft!