Not an Easy Win
Help students explore resilience, identity, and second chances with Not an Easy Win—a powerful middle grade novel that blends SEL and storytelling in meaningful ways. Build empathy through real-world themes. Teach character development with depth. Use discussion to support emotional growth. Connect literacy with life skills. Perfect for Grades 5–8 teachers, counselors, and book clubs.
Helping Students Understand Resilience, Identity, and Second Chances: A Classroom Experience Inspired by Not an Easy Win
Have you ever noticed how some students carry more than what we see?
They react quickly.
They shut down.
They push back.
And underneath it all…
they’re trying to be heard.
That’s exactly what Not an Easy Win brings to light.
Book Snapshot
Title: Not an Easy Win
Author: Chrystal D. Giles
Publisher: Random House Books for Young Readers
Age Range: 10+
Grade Level: 5–8
Genre: Contemporary Realistic Fiction
Themes:
Resilience & self-discipline
Identity & belonging
Friendship & trust
Incarcerated parents
Second chances
A Story That Feels Real (Because It Is)
Lawrence’s world has been turned upside down.
New town.
New school.
New rules.
And when things go wrong… they really go wrong.
After being expelled, Lawrence finds himself at a rec center—where chess becomes something more than just a game.
It becomes:
A way to think before reacting
A way to understand consequences
A way to rebuild trust
👉 A way forward.
As noted in the guide, Lawrence begins to see that “life is hard… and we’ve had a double dose of hard lately” (p.4), grounding the story in real emotional truth .
Why This Book Matters (Teacher Pain Points)
Perfect for classrooms where:
Students struggle with emotional regulation
Behavior is often misunderstood
SEL conversations feel surface-level
Representation and real-life issues matter deeply
Teachers need meaningful discussion starters
What Students Will Learn
How self-discipline develops over time
The connection between choices and consequences
Empathy for peers with different life experiences
How conflict can evolve into connection
Strategic thinking through the metaphor of chess
What’s Inside This Educator Guide
This guide is rich with discussion and reflection:
Pre-reading analysis of cover and theme
Deep, text-based discussion questions
Vocabulary tied to real-life application (logic, intention, nemesis)
Character analysis and relationship shifts
Writing prompts grounded in personal connection
CCSS-aligned reading, writing, and speaking standards
Standout Activity: Pinwheel Perspectives (Character Analysis)
This is SUCH a strong, visual thinking tool.
From the template on page 3, students:
Analyze Lawrence vs. Deuce
Track their shift from rivals → allies
Explore the powerful line:
👉 “He is you.” (p.135)
Students break down:
Differences
Similarities
Challenges
Growth
👉 It turns abstract character development into something students can see and map.
A Powerful Thread: From Conflict to Connection
One of the most meaningful arcs in the story:
Lawrence and Deuce begin as adversaries…
…but through shared experiences, music, and understanding, they become something more.
As the guide highlights, their journey reflects how people can “pull someone else up” through empathy and connection .
Try This in Your Classroom
SEL-focused novel studies
Small group or book club discussions
Character analysis units
Conflict resolution lessons
Cross-curricular connections (literacy + life skills)
Download the Free Educator Guide
Ready to bring meaningful, student-centered conversations into your classroom?
👉 Download the full educator guide here: Standards-Aligned Educator Guide for Grades 5 – 8
About the Book Link (Transparency Note 💛)
If you’d like to explore or purchase Not an Easy Win, you can use the link below:
This is an affiliate link, which means I may earn a small commission (at no extra cost to you). These earnings help support the creation of free Guides by Deb resources for teachers and classrooms.
This guide is part of my Guides by Deb collection—standards-aligned resources designed to help educators turn great books into meaningful learning experiences.
I’m Debbie Gonzales, author, educator, and founder of Pin Lit Marketing, where I help children’s book creators grow their visibility through Pinterest.
Together, this work connects books, educators, and readers in lasting ways.
