GUIDING FAMILIES, CAREGIVERS, & EDUCATORS
to Prepare Elementary Students for Middle School Success
Let’s Give Every Child the Chance to Succeed.
Far too many students struggle to meet the demands of middle school, but it doesn’t have to be that way. We empower families, caregivers, educators, and educational organizations with executive function skills, lifelong learning tools that help students develop self-discipline, time management, organization, reflection, and study habits.
"I was once a child who felt invisible and lost in school. One caring adult provided a stable environment and the encouragement I needed to learn. You have the power to do the same for your child."
CHERYL WILSON
Speaker Kit
Bring Dr. Cheryl Wilson to Your Stage
With over 25 years as a teacher, principal, and consultant, Dr. Cheryl Wilson inspires families, educators, and caregivers with practical strategies that help children succeed in school and life. Her talks are heartfelt, empowering, and full of actionable tools.
20+
Years of Empowering Students' Lives
100+
Parents, Schools and Organizations Served
4,000+
Success Stories and Lives Changed
Why Early Preparation Matters
Building a Brighter Future: Why Life/Executive Function and Academic Skills Matter
Success isn’t just about what you learn but how you learn and apply life/ executive function skills such as self regulation, time management, and organization to help students stay focused, set goals, and follow through. Academic skills like critical thinking, asking questions, and using memory strategies make learning stick. Mastering life and academic skills helps students navigate challenges, build confidence, and prepare for a successful future in any path they choose
Without life and executive function skills, students entering middle school often struggle with managing their time, staying organized, and completing assignments independently. This leads to frustration, missed deadlines, and declining confidence in their ability to succeed.
Lacking study skills, students may rely on last-minute cramming, struggle to retain information, and find it difficult to analyze or apply what they learn, making school increasingly overwhelming and discouraging.
With the right support and coaching, families and teachers can actively teach, monitor, and reinforce executive function/life and study skills, helping students develop independence, confidence, and the habits they need to thrive in middle school and beyond.
The good news? With the right support, struggling students can thrive. That’s where we come in.
SERVICES
How We Can Help
Personalized Coaching & Building Skills - Our Formula for Results
We help students develop essential life/executive function and study skills by first coaching and supporting families, their child’s first teacher. When families learn, model, and monitor life/executive function and study skills, students are more likely to adopt these habits, leading to long-term academic success and future career readiness.
SERVICES
How We Can Help
Personalized Coaching & Building Skills - Our Formula for Results
We help students develop essential life/executive function and study skills by first coaching and supporting families, their child’s first teacher. When families learn, model, and monitor life/executive function and study skills, students are more likely to adopt these habits, leading to long-term academic success and future career readiness.
Our Proven Method = Powerful Results
At I Can Learn Anything, we take a multifaceted approach to ensure each child’s unique needs are met:
Personalized Learning Programs
We use a strengths-based approach to personalize learning. We help students first discover and identify their natural abilities, interests, and talents. Tailoring learning based on students' strengths as opposed to their weak areas improves their self-confidence, engagement, and focus.
Life/Executive Function Skills Coaching
To increase motivation and success, we model and use the student's strengths to teach executive function skills. Students are more willing to engage in activities that build on their talents and interests. Learning self-control, how to manage their time, organize, stay focused, and set goals now have practical applications.
Study Skill Development
We connect real-life applications to introduce study skills. Students brainstorm the habits of their favorite role models. They discover that repeated practice, learning from mistakes, writing notes, learning from and teaching others, and planning for events and the future are study habits that lead to success.
Support for Families and Educators
Student success and outcomes are dependent upon coaching and teaching families and educators through ongoing communication, professional development, and multiple learning opportunities.
ABOUT Cheryl Wilson
Meet Cheryl Wilson
Ed.D., Educational Consultant, Speaker, & Author
My journey from a struggling, invisible student to an empowered learner, mentor, teacher, and principal inspired my mission to ensure no child feels invisible or unsupported.
For over 25 years, I dedicated my life to equipping students with the skills to succeed academically and socially, fostering environments where they feel seen, valued, and capable of charting their paths to success. In 2020, I retired and substituted at a middle school. For three years, I watched as students, especially those who were low-
performing and ill-prepared, were promoted to high school. Knowing that such students may drop out of high school in 9th or 10th grade influenced my decision to end my retirement. With the help of families and teachers, I want to end the trend of students entering middle school without self-regulation, organization, life/executive function skills, and study skills to actively participate in and fulfill the middle school expectations and standards. These essential skills and habits will allow them to flourish throughout their lives.
As a public speaker, I aim to educate caregivers, educators, and agencies on the profound impact of teaching students how to learn and apply executive function skills and study strategies. Skills that must be taught from kindergarten through twelfth grade so that all students take ownership of their learning and become independent learners.
Watch for my upcoming book on Amazon, When Decisions Disrupt Your Sleep, written to help school leaders lead with courage, clarity, and care.
I Am the Time to Learn Speaker
In addition to being a teacher and principal, I have also volunteered and taught young men in juvenile hall, mentored teenage mothers, and served as a Court Appointed Special Advocate (CASA) for foster youth. However, none of those experiences prepared me to be a caregiver for a 9-year-old boy who has struggled in school for the past three years. I understand firsthand the emotional strain and pressure that families feel when their child lacks the skills, motivation, and focus to meet grade-level standards. As a public speaker, my goal is to empower families, caregivers, and educators with practical strategies, proven methods, and compassionate support to help children develop the executive function, study skills, and confidence needed to thrive in school and beyond.
"The little ones are her reason for being. Alas, the time has come for her to be seeing a new path ahead, new folks to be led. Ruby staff bids a fond farewell to you, Cheryl, with tender feelings."
Thanks for the memories, With love, Your Ruby Bridges Staff
What families say
"Thank you so much for helping to make this a great first year at LeConte for us. You are truly a gem for this school (and I don't even know 10% of what you do). You make all the kids feel special. You're a great inspiration to the kids, parents, and teachers, with each passing month of the school year we've appreciated LeConte more and more."
What Clients Say
What Clients Say
What’s Really Holding Students Back?
The lack of executive functioning skills—such as organization, time management, and self-regulation—sets many children up for failure before they reach high school. Add to this the anxiety of falling behind, and we see a cycle that leads to high dropout rates.
