What If Learning Faster Just Meant Making Mistakes Cheaper?

An art teacher’s observation about pencils vs. pens reveals everything wrong with how we design organizations

“In my classes, I’m very careful to talk about what failure means. It means trying something new and not getting the right result the first time.”

— Stephen Thorpe, a painter who teaches foundations at SCAD, told me that students who use a pencil do better than those who use a pen.

I love this quote from Keith Sawyer’s wonderful book, “Learning to See,” because it gets at something we fundamentally misunderstand about failure in business. We talk about “failing fast” and “learning from mistakes,” but then we design systems that make every error feel permanent, every misstep visible to the entire organization, and every experiment a potential career-limiting move. We’re writing in pen when we should be sketching in pencil.

Stephen Thorpe’s observation about his art students is so much more than a simple teaching tip; it’s a design principle. Students who use pencils produce better work not because they make fewer mistakes, but because they make more mistakes and correct them faster. The eraser changes the psychology of the work. With a pencil, you’re not committed to every line. You can try something, see if it works, and adjust. With a pen, every mark is a decision you have to live with. The pen student spends more time planning, hesitating, and second-guessing. The pencil student spends more time doing, learning, and iterating.

Now the question becomes: what does your organization use? Because most companies are handing their teams permanent markers and then wondering why nobody wants to draw.

The pencil equivalent in business isn’t a tool; it’s a system. It’s the difference between launching a product to your entire customer base versus rolling it out to one percent and watching what happens. It’s the difference between a six-month planning cycle and a three-day prototype built from index cards and Sharpies. It’s the difference between quarterly performance reviews where mistakes are documented and daily standups where problems are surfaced while they’re still cheap to fix. The pencil equivalent is any mechanism that makes the cost of being wrong so low that people actually try things.

That’s the real lesson from Thorpe’s pencil students. It’s not about the tool; it’s about the cost of correction. When correction is cheap, you experiment more. When you experiment more, you learn faster. When you learn faster, you find what works while your competitors are still planning their one perfect attempt. The speed of learning is inversely proportional to the cost of failure. Make failure cheap, and learning becomes fast. Make failure expensive, and learning grinds to a halt.

What’s your pencil?

@Pascal

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