Navigating the Middle School Years: Win Big! And Lose Big Too. It’s OK.

Name the movie:

Head Valet: To win big you gotta do what? 
Carparkers: Lose. 
Head Valet: Lose big. What are we doing now? 
Carparkers: We're losing big. 

You have to finish the article for the answer. I’ll tell you this: It the film, the main character’s fear of losing initially prevents him from pursuing what he truly wants, both in terms of love and life choices. Overcoming this fear and being open to new possibilities is an important theme in the film.

Overcoming the fear of losing is no easy task, and as an educator for 27 years in the middle school hallway, I saw it a lot.

For many parents, watching their child transition through the middle school years is a bittersweet experience. It’s a time of remarkable change, where kids start to grow into the young adults parents have always envisioned. This period of transformation is often filled with moments of pride as children develop their personalities, academic habits, and social skills. However, it’s also a time that can bring unexpected challenges.

Middle school is notoriously tricky, both for kids and their parents. It’s a time when students face new pressures, develop emotionally, and start to wrestle with their sense of identity. And because it’s hard for kids, it’s hard for parents too. No one wants to see their child struggle, and those struggles—no matter how small—can feel overwhelming. Whether it’s a dip in grades, a friendship issue, or a loss of confidence, watching your child face challenges is emotionally draining.

The Bigger Picture

When challenges arise, it’s important to take a step back and see the bigger picture. For example, getting a B on a report card when all the other grades are A’s can feel like a loss. A big loss. But in the grand scheme of things, it’s a small bump in the road, and it is a necessary bump in the road. Parenting often involves recalibrating expectations and reminding yourself that progress is more important than perfection. And perfection is, well, impossible.

That’s not to say it’s easy. Every parent has hopes and dreams for their child. When those benchmarks aren’t met—whether academically, socially, or emotionally—it’s hard. But these moments of struggle are when growth happens, for both children and parents.

Embracing Support

One thing that can make this journey smoother is seeking support when needed. As someone who runs a tutoring company, I’ve seen firsthand how an extra layer of academic (and emotional) support can make a significant difference in a child’s middle school experience. I wish every family had the resources and awareness to access this kind of help. Unfortunately, there’s often a stigma attached, but it’s essential to normalize the idea that everyone benefits from support.

A Time of Growth

If you’re a parent sending your child through middle school for the first time, here’s my biggest piece of advice: Expect bumps in the road. Expect to lose big in order to win big. It’s a mandatory part of life, and it’s the best way to learn how to succeed. Supplement with help – maybe from a tutor – but be ready to embrace the bumps. Use them as teaching moments. Let your child know that failure is a critical part of life. It’s how we grow, learn resilience, and ultimately understand the value of success.

In the meantime, celebrate all the wins—big and small. Whether it’s mastering a math problem, making a new friend, or trying something new, every win is worth acknowledging.

Middle school is designed to be a time of growth, and growth rarely happens without a little discomfort. Be prepared for tough moments, but also be ready to reassure your child that they don’t last forever, and the big wins will come.

It’s Some Kind of Wonderful.