Middle School Success Coaching
Helping Middle Schoolers Build Confidence, Independence & Executive Functioning
Middle school is a time of enormous growth—academically, socially, and emotionally. At this stage, students begin to think more abstractly, plan for the future, and take ownership of their learning. But they also face new challenges: managing responsibilities, regulating emotions, and developing independence. Without support, they can feel overwhelmed, frustrated, or disorganized.
For parents, this transition can feel just as daunting. The strategies that worked in early childhood may no longer be effective, and as your child grows and changes, your relationship is shifting too. It’s common to feel uncertain about how to provide the right support. That’s where I come in.
With years of experience working with middle schoolers in both traditional and alternative education settings, I help students develop the skills they need to become more independent and confident.
Through personalized coaching, I support:
Executive Functioning Skills – Time management, organization, task initiation, and self-monitoring.
Emotional Regulation – Understanding and managing emotions effectively.
Self-Advocacy – Learning to ask for help and communicate needs.
Independent Learning – Taking initiative, problem-solving, and setting goals.
Resilience and Adaptability – Handling setbacks with confidence and adjusting to new situations.
Scroll to the bottom of the page to read the Lee Family’s story and how my one-time coaching session helped give their daughter Jane the tools to support her independent learning.
Want to explore how I can support your middle schooler? Contact me and let’s start the conversation!
I often get asked “Why Middle Schoolers?”
Middle school is a magical in-between—where childhood and adolescence meet. At this age, kids still crave play, imagination, and adventure, yet they also long for responsibility, independence, and respect. They are capable, passionate, and full of energy. They care deeply—fierce advocates for justice, endlessly curious, and eager to explore their own identities.
They are discovering what excites them and what feels frustrating or dull. One moment, they’re lost in deep conversation, thinking critically about the world, and the next, they’re chasing each other around the room in a burst of laughter. They want to be trusted, to be taken seriously, to learn real-life skills like cooking and money management. At the same time they want to still snuggle up for a bedtime story, or have pretend adventures in the backyard.
Too often, middle school is seen as a waiting period—a bridge between the innocence of childhood and the responsibilities of high school. But I see it differently. Middle schoolers aren’t just full of potential—they are already living it.
What they need most is a space where they can be both—growing into independence while still embracing play. A space where they are met with honesty, respect, and genuine connection. That’s what I strive to create for every middle schooler I work with.
The Lee Family’s Story
The Challenge:
Helping a middle school student develop executive functioning skills to improve task initiation, work completion, and overall independence.
The Lee* family reached out for support as they navigated homeschooling with their middle schooler, Jane*. While homeschooling provided a more conducive learning environment overall, they found it challenging to balance their full-time work schedules with Jane’s need for guidance in staying organized, starting tasks, and following through on assignments.
"While we’ve enjoyed the academic freedom and rigor of homeschooling, our day-to-day reality means I don’t have the time to walk my child through each task every day. We had tried various to-do lists and tracking methods, but ultimately, we reached out to Jessie for her expertise in supporting middle schoolers with executive functioning strategies."
The Solution
I began with a one-on-one consultation with Jane’s parents to openly discuss their homeschooling experience so far—what was working, what wasn’t, and Jane’s personal goals. Together, we set clear objectives and planned for an in-person coaching session in their home.
During our session, Jane was in the middle of an art project when I arrived, so we eased into a natural, curiosity-driven conversation while she painted. I guided Jane in identifying challenges and brainstorming solutions and allowed her to take the lead in the conversation. We explored different strategies, discussing how her needs varied across subjects, and Jane was able to voice which approaches she thought would be most effective for her learning style. By the time she completed her art piece, we had built a strong foundation of strategies tailored to her goals. After the meeting, I organized the notes into a clear, practical guide for the Lee family, along with tips for implementation.
The Results
"Jessie’s ability to connect with Jane on her level, meeting her where she was and skillfully guiding the conversation, created an engaging and insightful discussion around strengths, challenges, and strategies. She took thorough notes and shared them with us afterward. At Jessie’s suggestion, Jane used those notes to create a visual strategy board on Canva that she can reference anytime.
At all times, the conversation was respectful, affirming, and yes—joyful! Beyond helping Jane, Jessie’s insights also gave us, as parents, a clearer understanding of how to support her independence. It was exactly what we had hoped for!”
*names changed for privacy
My meeting with Jane
The Lee family’s experience reflects my approach to middle school coaching—helping students take ownership of their learning while giving parents the tools to provide the right level of support. If your middle schooler is struggling, I’d love to help.
Let’s Get Started
The first step is a free 30-minute consultation where we’ll talk about your middle schooler and their goals and challenges. From there, we can choose the service or package that’s the best fit for your family. For coaching, I can meet in person in the Joyful Horizons space in Richmond, in person in your home in Chittenden County, or online from anywhere! Coaching can vary from a one-time meeting to regular weekly or monthly sessions.
Ready to take the next step? Sign up for a time slot on my calendar or send me a message to start the conversation. I can’t wait to help your middle schooler thrive!