Finding Wins: Building Confidence Through Small Successes
Introduction: The Power of Small Wins
For so many students, math is a cycle of frustration. They try, struggle, fail—and over time, they begin to believe that they’re just not good at math. Their confidence erodes. They disengage. They stop trying.
But what if success wasn’t about mastering everything all at once?
What if confidence in math wasn’t built through significant milestones but through small, consistent wins that prove to a student, over and over again, that they are capable, that they can make progress, that they are not stuck?
This idea comes from the work of Dan Sullivan and Dr. Benjamin Hardy’s book, The Gap and the Gain. The concept is simple:
🔸 The Gap is when we measure progress against where we wish we were—constantly feeling behind, focusing on what we don’t know.
🔹 The Gain is when we measure progress against where we started—recognizing every step forward, no matter how small.
For students who struggle with math, living in “The Gap” reinforces failure. But when we shift their focus to “The Gain”—what they have accomplished—it breaks the cycle of discouragement and fuels confidence.
In this article, we’ll explore:
✔ How to shift students from “The Gap” to “The Gain” in math learning.
✔ Why “stacking wins” is the key to breaking the cycle of failure.
✔ Practical strategies to help students experience small, consistent successes—ones they can see, feel, and build upon.
Because confidence in math doesn’t come from hearing “You can do it”—it comes from experiencing real, recent success.
And that’s what we’re here to create.
Understanding “The Gap” vs. “The Gain” in Math Learning
For many students, math is a constant reminder of what they can’t do. They compare themselves to their classmates, see a low test score, or struggle with a new concept—and suddenly, math isn’t just hard. It’s proof that they’re “not a math person.”
This way of thinking is what Dan Sullivan and Dr. Benjamin Hardy call “The Gap.”
What Is “The Gap” Mindset?
When students are stuck in The Gap, they:
🔸 Measure themselves against an impossible standard (perfection or where they “should” be).
🔸 Feel like progress isn’t enough—if they’re not “caught up,” they’re still failing.
🔸 Focus on what’s missing instead of how far they’ve come.
📌 Example of The Gap in Math Learning:
A student gets 7 out of 10 correct on a quiz. Instead of seeing the 7 problems they solved successfully, they obsess over the 3 they missed. The focus is on what’s wrong—not what’s working.
A gap-focused mindset often leads to math anxiety, where students feel overwhelmed, avoid math tasks, and doubt their ability to improve. To understand more about how mindset impacts learning, check out Modeling a Growth Mindset and Recognizing Early Warning Signs of Math Anxiety.
Shifting to “The Gain” Mindset
“The Gain” is about measuring progress based on how far you’ve come rather than how far you have left to go.
When students are in The Gain, they:
✔ See their progress as a success, no matter how small.
✔ Focus on what they’ve learned, not just what they haven’t mastered yet.
✔ Feel motivated to keep going because they recognize their growth.
📌 Example of The Gain in Math Learning:
That same student got 7 out of 10, correct? Instead of focusing on the 3 mistakes, they say, “Last time, I only got 5 right—this is progress!” They feel encouraged, which makes them more likely to keep engaging with math.
How Parents & Educators Unintentionally Reinforce “The Gap”
Even with the best intentions, parents and teachers can accidentally push students further into The Gap by:
🚫 Saying, “You just need to try harder” – Reinforces the idea that success is about effort rather than recognizing progress.
🚫 Only celebrating outcomes – Focusing on test scores, grades, or finishing a topic instead of minor improvements.
🚫 Comparing them to “where they should be” – Instead of measuring their progress against where they started.
Instead, we can help students shift into The Gain by:
✔ Noticing and celebrating small wins – “You got more correct than last time!”
✔ Framing mistakes as growth – “That mistake helped us see what we need to work on next.”
✔ Helping them track their progress – Using visual growth charts, reflection journals, or goal-setting.
When students see evidence of their improvement, they start believing they can succeed.
And that belief is what breaks the cycle of failure.
Stacking Wins: Why Small Successes Matter
Math anxiety doesn’t start overnight—it builds over time. Many struggling students experience a repeated cycle of failure: they try, they struggle, they fail, and eventually, they stop believing that success is even possible.
This is why small wins matter.
When a student starts to experience consistent success—even in tiny ways—it rewires their brain’s response to math. Instead of expecting frustration and failure, they associate math with progress and possibility.
📌 For more on how math anxiety affects students’ learning experiences, read Helping Neurodiverse Students Overcome Math Anxiety.
How Small Wins Change the Brain
Our brains are wired to seek out rewards. When we accomplish something—even something small—our brain releases dopamine, a neurotransmitter associated with motivation and learning.
🔹 Failure Cycle: A student tries → struggles → gets discouraged → avoids math → struggles more.
🔹 Success Cycle: A student wins (even a small win) → feels motivated → keeps going → builds confidence.
Each time a student experiences and recognizes a win, they reinforce the belief that they can succeed. Over time, these small successes stack up into real, lasting confidence.
📌 Example: A student who believes “I’m bad at math”
They finally master multiplication facts for the 3s times table.
Instead of saying, “But I still don’t know my 7s,” we help them focus on how much they improved.
The student feels capable. They keep going instead of shutting down.
This is why we must actively create opportunities for students to win—frequently, visibly, and consistently.
The Psychological Impact of Winning
🔹 Wins build momentum.
A student who successfully solves one type of problem is more likely to try another.
🔹 Wins reduce fear.
If a student only experiences math as failure, they will continue to fear it. Wins create safety.
🔹 Wins help reframe self-belief.
When students see their own success, their internal dialogue shifts from “I can’t do this” to “I’m getting better.”
The key? These wins must be intentional.
It’s not enough to hope students recognize their progress—we need to design learning experiences that create and highlight these wins.
📌 To learn more about how scaffolding can support struggling students in building small, achievable wins, check out Overcoming Math Anxiety Through Scaffolding.
Practical Strategies to Create and Celebrate Wins in Math
Small wins don’t happen by accident—they must be intentionally designed into the learning experience. When students see their own progress, it fuels confidence and keeps them engaged.
Here’s how parents and educators can structure learning to create, reinforce, and celebrate small wins consistently.
1️⃣ Find the Last Success: Start Where They Can Win
Many struggling students feel like they fail at every step in math. Instead of starting at frustration, start at success and build from there.
✅ How to apply this:
Begin with a problem they can already solve before introducing something new.
Use “warm-up wins”—quick review problems that remind them, “I can do this.”
If a student is struggling, back up until you find a skill they feel confident in, then build forward.
📌 Reference: If a student has deep-rooted math anxiety, reinforcing past wins can help shift their mindset. Read more in this article on modeling a growth mindset.
2️⃣ Break It Down: Make Every Step Winnable
Big math challenges can feel overwhelming. Breaking problems into tiny, achievable steps helps students see progress before they reach the final answer.
✅ How to apply this:
Use scaffolding to support understanding (e.g., solve part of a problem together, then let them finish).
Turn multi-step problems into mini-goals—“First, we’ll set up the equation. That’s a win!”
Let them celebrate process wins, not just correct answers.
📌 Reference: Scaffolding makes math more approachable and helps prevent students from shutting down. Learn more in this blog on scaffolding.
3️⃣ The Power of Visible Progress: Track Wins Over Time
Many students struggle to recognize their own progress. Tracking wins in a visible way helps them “see” their growth.
✅ How to apply this:
Use a progress chart to track skills they’ve mastered.
Have students reflect on past struggles—“Remember when this was hard for you?”
Try a “Win Journal,” where they write down something math-related that went well each week.
When students see proof that they’re improving, it shifts their mindset from “I’m bad at math” to “I’m getting better.”
4️⃣ Reframing Struggles: Teach Students to Recognize Growth
Many students only measure success by perfection. Instead, teach them to see their growth—even in mistakes.
✅ How to apply this:
Shift their focus from correct vs. incorrect to “What did I learn from this?”
Encourage re-attempts without pressure—“What could we try differently?”
Help them track how many mistakes they’ve corrected, not just how many they made.
📌 Reference: If your child feels like mistakes mean failure, check out this article on supporting neurodiverse learners in math.
5️⃣ Play to Strengths: Use What They Enjoy to Create More Wins
Every student has strengths—even if they struggle with math. When we connect math to what they’re naturally good at, we create built-in confidence boosts.
✅ How to apply this:
Use interests as a hook—sports stats, coding, puzzles, or hands-on activities.
Let them show understanding differently—drawing, verbally explaining, and using manipulatives.
Highlight skills they already have—“You’re great at patterns! That will help with multiplication.”
By framing math in a way that plays to their strengths, students feel capable instead of defeated.
Conclusion: Shifting the Cycle from Failure to Confidence
For students who struggle with math, confidence isn’t built through reassurance alone. It’s built through real, tangible successes—they can see, feel, and believe in it.
When we shift from “The Gap” to “The Gain,” when we stack small wins consistently, we transform math from a source of stress into a place where success feels possible, repeatable, and inevitable.
Making Wins a Daily Practice
✅ Start where they can win – Build on past successes to create momentum.
✅ Break challenges into winnable steps – Turn overwhelming problems into bite-sized victories.
✅ Track progress visually – Help students see how far they’ve come.
✅ Reframe mistakes as growth – Shift the focus from perfection to improvement.
✅ Use strengths-based learning – Connect math to what they already do well.
Confidence isn’t about being perfect—it’s about believing you can improve.
Your Next Steps: Supporting Your Child’s Confidence in Math
📌 Want to help your child shift from focusing on failures to recognizing progress?
👉 Read Modeling a Growth Mindset and Recognizing Early Warning Signs of Math Anxiety
📌 Looking for more strategies to help struggling learners break the failure cycle?
👉 Read Helping Neurodiverse Students Overcome Math Anxiety
📌 Need help making math more approachable and breaking down big challenges into winnable steps?
👉 Read Overcoming Math Anxiety Through Scaffolding
By creating consistent wins, we don’t just teach students math—we teach them that they are capable, resilient, and stronger than they think.
And that belief? It changes everything.
