Failing Well: The Hidden Engine of Deep Learning

How mistakes, struggle, and reflection build stronger, more resilient students.

I was talking to a student when I first used the phrase failing well. We were going over feedback I’d given him on an essay, and as I scanned my comments, I remembered a concept I’d encountered during a recent International Baccalaureate MYP curriculum workshop. The term had stuck with me.

I told him his essay was a living thing—something that could grow and improve over time, especially as he learned to harness his vast potential. But to get there, he needed to accept the feedback, reflect on it, and use it to move forward. I could tell this wasn’t yet second nature for him. If I’m honest, it wasn’t fully second nature for me either. But the phrase felt right—more right, at least, than assigning an arbitrary score that wouldn’t help him push the work forward.

Failing well isn’t new. It’s known by many names and embraced in many disciplines. At its core, it’s the idea that setbacks, mistakes, and challenges are not obstacles to learning—but essential to it. It’s not about merely tolerating failure, but about using it. Analyzing it. Removing the shame and fear from the equation. Failing well helps students develop metacognition, resilience, and a growth mindset (more on that in a future post!).

This kind of learning doesn’t come from a grade. It comes from a process—trial and error, reflection, feedback, iteration. Success isn’t the opposite of failure. It’s often built on top of it.

At Pathways, this idea runs deep. Design thinking—one of the cornerstones of our curriculum and ethos—is grounded in failing well. So is our entrepreneurial focus. Whether a student is prototyping a product, drafting an essay, or developing a new idea from scratch, they’re encouraged to test, revise, and grow. The goal isn’t to get it perfect the first time. It’s to keep improving.

Here are two studies that underscore why failing well matters:

Study: Kapur (2014) – Productive Failure in Math Learning
Design: Middle school students were asked to solve math problems before receiving instruction on the concepts. After struggling with the problems, they were taught the formal content.
Findings: Although students in the "productive failure" group performed worse at first, they later outperformed those who received direct instruction from the beginning—especially on tests of conceptual understanding and knowledge transfer.
Implications: Struggling with unfamiliar material helped students engage more deeply and made the instruction that followed more meaningful and long-lasting.

Study: Hattie, J. (2009) – Visible Learning
Summary: In a meta-analysis of over 800 studies, Hattie found that “errors and mistakes” paired with quality feedback had a high effect size (0.72).
Implication: Students benefit most when failure is framed as part of the learning journey—something to learn from, not something to fear. When feedback is timely, specific, and actionable, achievement rises significantly.

At Pathways, we’re building a place where students aren’t punished for not getting it right the first time. Instead, they’re supported to try again—and again—with new tools, new strategies, and growing confidence.

Because in the real world, failing well is often the first step toward doing something great.

Warmly,
Rob
Founder & Director, Pathways

About Rob & The Pathways School
Rob Wilson is an educator, writer, and father of two with over 20 years of experience in international, progressive, and experiential education. From rural Maine to Hong Kong, and now Spain, his journey has always revolved around one question: how can we help young people learn in ways that are meaningful, joyful, and truly prepare them for the future?

Born out of this question, The Pathways School is Rob’s answer. Launching in Southern Spain in 2027, Pathways is a high school that blends personalized, project-based learning with real-world readiness and ecological living. At Pathways, students design their own educational journeys—with the guidance of mentors, experts, and peers—rooted in curiosity, purpose, and deep connection to the world around them.

To follow the journey or get involved, subscribe to the blog or reach out. Let’s build something better—together.