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Designing to Fail: Turning Mistakes into Breakthroughs

"Designing to fail" not only releases the pressure of “getting it right” from the start. It also opens up a relaxed, low-stake space of play where the unexpected becomes a source of innovation. By designing to fail, you shift your mindset from fear of failure to curiosity about the unexpected. Failure is no longer an obstacle but a creative springboard. 
Challenge card 012. Design to fail
Photo background by Brett Jordan on Unsplash

Table of Contents

This sounds radical, but the proposition is clear: analyse all the decisions and elements that could make your idea fail, use them as inspiration to generate absurd ideas, and then invert those ideas to find unexpected but effective solutions.

This approach not only releases the pressure of “getting it right” from the start but also opens up a relaxed, low-stake space of play where the unexpected becomes a source of innovation.

This technique is also related to Edward de Bono’s lateral thinking method:

Let’s explore how to apply this technique through the Experimenter lens in the different phases of the creative process to transform your way of creating.

Empathise: Understanding failure as a starting point

The first step is to put yourself in the user’s shoes, but this time from a failure perspective. Ask yourself: What would frustrate my user? What aspects of the design could cause confusion, discomfort or rejection?

For example, imagine you are designing a public library. You could list elements such as: “the books are out of order,” “the signage is confusing,” or “there is not enough lighting.” These initial “failures” will help you identify what should not happen. By reversing them, you could discover unique solutions: what if the signage was interactive and tailored to each user?

Define: Rewrite failure as an opportunity

Organise the failure ideas you identified in empathy and turn them into a key question: How could we avoid the user feeling lost? How could we create a pleasant experience even in the darkest spaces?

These questions redefine the problem and help you focus on what matters. In the library example, you could prioritise questions like: “How can you transform the act of finding a book into a game?”

Create: Absurdity as a creative engine

This is where the magic happens. Use the identified failures as springboards to generate crazy ideas; the more absurd, the better! Remember that your goal is to use the ideas to start thinking differently.

Imagine you identified that “not finding a book would frustrate the user.” What if you designed shelves that move to hide books? Although it seems ridiculous, this idea could lead to mobile shelves that automatically reconfigure to optimise space or even an app that guides you to the book with a video game-like experience.

Designing to fail forces you to pinpoint what doesn’t work, guiding you to solutions that do.

Prototype: Build to Fail, Learn to Succeed

The Prototype phase is where failure becomes tangible. Here, low-fidelity mockups and rapid iterations allow you to test out flawed ideas and learn from them without significant investment.

Prototype the resulting ideas. Don’t be afraid of imperfections; remember that the goal is to learn from the process. For example, you could build a physical prototype of mobile shelving out of cardboard or simulate the app experience with a storyboard.

The more prototypes you test, the more likely you will discover relevant and innovative solutions. This iterative approach will allow you to filter out the absurd and turn it into real functionality.

Test: Iterate Through Feedback

The Test phase is where failures from prototyping meet user feedback, creating an iterative loop of discovery and improvement. Testing your “failures” deepens your empathy and refines your solutions.

Testing flawed prototypes gives users permission to critique and engage, revealing deeper insights than polished designs might allow. As Tim Brown highlights, 

Why Designing to Fail is the Experimenter’s Superpower

By designing to fail, you embrace the core principles of the Experimenter: rapid iteration, low-resolution prototyping, and fearless creativity. You shift your mindset from fear of failure to curiosity about the unexpected. Failure is no longer an obstacle but a creative springboard. 

Designing for Learning, Not Perfection. Challenge Card 012 reminds us that failure isn’t the enemy—it’s a guide. Experimenters know they pave the way for success by seeking out failures early. It’s not about getting it right on the first try; it’s about learning fast, asking the right questions, and iterating forward.

From Absurdity to Breakthrough. The Experimenter’s mindset transforms absurd failures into surprising insights. Failures highlight hidden user needs. When flipped, these insights lead to solutions that delight and inspire.

Dare to Fail, Dare to Innovate

Failure isn’t a barrier—it’s a springboard. By designing to fail, you embrace the Experimenter’s spirit of curiosity, resilience, and play. You create learning opportunities, uncover hidden insights, and iterate toward groundbreaking designs.


  1. Edward de Bono (1991). Pensamiento lateral. Barcelona: Paidós, p. 179. ↩︎
  2. Scott Witthoft (2022). This is a Prototype. California: Ten Speed Press, p. 168. ↩︎
  3. IDEO (2015). The Fieldguide to Human-Centred Design. San Francisco: IDEO, p. 21. ↩︎

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