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Your Back to School Guide

Jessi Cruickshank on Back to School Balancing Family, Fun & Fresh Starts


An exclusive Q&A with Jessi Cruickshank as she shares her insights on navigating the back-to-school season with her family. Discover her tips for maintaining balance, fostering a love for learning, and making the transition from summer to school smooth and enjoyable for everyone.

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How do you encourage your children to be excited about learning and school activities?

Thankfully, my kids ARE excited about going back to school! I think for my generation, growing up in the 90s/2000s – we were all raised with this Bart Simpson mentality that “School Sucks”.  There was this pervasive cultural mindset that we were supposed to hate school and everything that went along with it. I don’t think that exists as much anymore, at least my twin boys don’t think that way yet. They can’t wait for Grade 1!

Plus, we have been reading Harry Potter together for the first time and I’ve been encouraging my boys to write journal entries and comic books all summer long, so they have started to understand the power of reading and writing. I think that is the key- our kids will get excited about learning, when they start to understand how it can unlock the world for them.

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How do you foster open communication with your children about their school experiences, both the good and the bad?

I am still figuring this out! I have learned that “how was your day?” or any general inquiry like that, won’t elicit any kind of meaningful response. I try to ask specific questions to each child “Rio, I wonder if you played with Carter at recess?” “Dray, did you paint or use pastels in art class?” the more pointed the question, the more likely they will answer it. Then, once we have a conversation going, I can try to dive deeper into their experiences at school.

Also, my kids are far more likely to engage with me about the meaningful stuff- friendships, teachers, worries… when we are alone together. Trying to carve out a little one-on-one time with each child, even if it’s just at bedtime or in the bath, is so important for my kids to feel heard and seen.

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How do you involve your family in the process for preparing for the new school year, from shopping for supplies to setting goals?

It’s funny- when I was a kid, we’d all go to the store to shop for school supplies or to the mall to pick out a new outfit. Now, we can order everything we need with the click of a button so we don’t need those rituals to prepare for the year ahead. 

Well, last year I decided to re-introduce the concept of “Back To School” shopping to my kids- I took each boy to the mall individually to pick out an outfit and a few supplies, just like my mom did with me. I realized they had never been into a clothing store, they had never tried on anything in a fitting room- it was all so foreign and exciting for them. They felt a sense of control over the start of the school year, which I think is important and a really special way to help prepare them for what’s to come.

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What advice would you give to parents who are feeling overwhelmed with the demands of back-to-school preparations?

Ignore the Internet. Your kid doesn’t need a new backpack, an apple watch or fancy markers. You don’t need to make a sandwich that looks like a cat or take a perfect back-to-school portrait complete with festive chalkboard and adorable outfit. Your child will not remember that. What they will remember is if they felt loved and supported going into the school year,  that is the most important thing you can provide.

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Lastly, can you share any fun or unique back-to-school traditions you have with your family?

All three of my kids collect keychains to hang on their school backpacks – the day before a new school year, we surprise them with a new keychain to hang on their bags. It’s a little reminder that mom and dad have their backs!


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