One Oregon School Leader’s Reflections on Easing into Back-to-School Season

As the final days of summer fade and the first signs of a new school year appear, Carrie Quinn, Executive Director of Insight School of Oregon at Painted Hills and mom of three school aged students, understands the emotional mix families often feel this time of year: equal parts excitement and exhaustion. For the Quinn household, summer break isn’t about chasing picture-perfect moments or extravagant getaways. Instead, it’s about something more meaningful: breathing room.

It’s the freedom to catch up on sleep, slow the day-to-day pace, manage sibling disagreements, and stumble through messy plans that occasionally turn into cherished memories. In short, summer is its own kind of classroom, where growth happens in everyday moments.

With one child in college, another in high school, and a third preparing to begin middle school, Mrs. Quinn sees summer as a built-in opportunity to pause and reflect. It’s not just a break from academics, it’s a chance to evaluate what’s working well at home, what needs to shift, and how to move forward with intention.

She encourages other Oregon families to resist the urge to sprint into the new school year. Before filling calendars and stuffing backpacks, her advice is to take a moment to reflect as a family. Ask questions like:

What experiences brought us the most joy this summer?

What moments felt draining or stressful?

What daily routines helped us function better?

What is one small change we can make that might set us up for a smoother school year?

Mrs. Quinn stresses that easing into a new routine doesn’t require a complete overhaul. Sometimes, it’s the little adjustments, like organizing meals in advance, staying on top of school communication, or building a consistent daily rhythm, that make all the difference.

In her own family, the current focus is supporting her youngest child through the transition from elementary to middle school. It’s a big transition full of new routines, adapting to new social situations, and preparing for the unknowns. Her approach is to anchor her child in the familiar.

That includes:

Offering consistent emotional support (with plenty of hugs, while they’re still welcomed)

Creating healthy boundaries around technology use

Reinforcing responsibilities, even when the response is a groan or an eye roll

And sometimes, those small efforts lead to surprising outcomes. After one especially stubborn bedtime routine, her son quietly said, “Thanks for helping me get to bed tonight. It actually feels good to have a shower and be in bed.” That simple sentence was a reminder of how much kids benefit from the stability and care that structure provides, even if they don’t always say so out loud.

Mrs. Quinn knows the parenting path isn’t easy, especially in the teenage years. It may seem like everyone else’s kids have unlimited freedom and zero expectations, but the truth is, most families are navigating the same challenging balance between boundaries and independence, fun and responsibility.

Her message to families is this: reflect on what’s working, be open to change, and know that support is always within reach. Whether you need a fresh strategy, extra encouragement, or just a reminder to slow down, even small steps can make the back-to-school season feel more manageable.

With a thoughtful approach, a calm mindset, and a willingness to adapt, families can enter the school year with a greater sense of ease and clarity. Mrs. Quinn’s advice: start small, be intentional, you’re not in this alone.

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