3 min read

How to Fail

Too often, the message being sent is "If I fail enough, I'll eventually succeed." Well, no, that's not how failure works. Failing on repeat doesn't achieve anything. There's nuance to failing.
How to Fail
An inbox search for 'iterate' and a few recent results. 

Iteration is an idea that comes up all the time. It's used with the assumption that iteration is how we learn. We're a team that prides itself of learning, so the frequent usage isn't surprising. The assumption could be stated as:

The faster you iterate, the faster you fail. The faster you fail, the faster you learn. Learning eventually leads to success. Or, (iteration → failure) → learning

Considering how much this assumption informs our thinking and decision-making, I think it deserves closer inspection. We need to stick it under the microscope and identify whether it's really the mechanism for learning that we assume it to be.

What is Iteration?

Imagine you're sitting down to write something. You write the first sentence, and then you write a second sentence, and then you start the third. But you realise that the first two sentences are way too grammatically complicated, and that they can be simplified. You change it, you're editing, you make typos, and go back and forth and back and forth, correcting and simplifying. That's iteration, the process of continually assessing and adjusting.

It's the same with cooking. You might know the ingredients and the method, but you still need to taste and adjust along the way. A little more salt, a little more spice, thickening or reducing as necessary. It's a real iterative process in which you keep edging closer and closer to the taste you want.

What's So Great About Iterating?

Iteration is valuable because it shows that failure isn't fatal. Your typo can be corrected, your sauce can be thickened. Being wrong is just the process of getting to the right answer.

The lesson presenting itself is that it's okay to fail. Not only is it okay to fail, it's necessary and encouraged. It's a valuable lesson, and one that's confirmed by almost anyone that's achieved anything significant.

Failure is the opportunity to see how we can productively move forward. Not to a world with no failure, but to a situation with different weak spots, ones worth patching over and coming out stronger. Failure is a feature. In most cases, the lesson stops there. It's wrapped up in a nice message that tells you that it's okay to fail, because failure is how you improve.

That's only half the story though, it stops at a critical stage. Too often, the message being sent is "If I fail enough, I'll eventually succeed." Well, no, that's not how failure works. Failing on repeat doesn't achieve anything. There's nuance to failing.

The reason failure is valuable is that it provides an opportunity to learn, but if you don't capitalise on that opportunity, your failure did nothing except waste time and money.

How Do We Actually Learn?

Failure facilitates learning, but it isn't where the actual learning takes place. Noticing things is how we really learn. Paying attention to what is happening and noticing patterns. Not just patterns of failure, but patterns of success, of opportunities taken or missed. Failure only teaches if you look back and observe. Failure only works if you reflect and change your model. Failing without reflection is a liability.

Failing is valuable because it allows you to develop hypotheses about how things work, which can then be tested against reality. Test with experimentation and curiosity. Look for anecdotes and data to back up your theories. Talk to people in different teams, companies and professions. Hear what they noticed when they failed and figure out what that means for you.

It sounds like a long process, but it doesn't have to be. You can do this over the course of a sprint (~2 weeks) by making the effort to notice things about your work. A sprint retro is the ultimate place to reflect on the things you've noticed and ask the rest of the team if they noticed the same things. Very quickly you begin to develop a deep understanding for what makes your team work and what makes it fail.


  • Failure without feedback is pretty useless.
  • No one wants systems with more failures, but they'll tolerate them as long as they facilitate learning. That only happens when you reflect.  
  • Silent failures prevent learning and improvement. Fail fast, fail loud.

p.s. As always, this is a theory that I'm trying to put to practice. If you disagree with it, I'd love to hear why.

Enjoying these posts? Subscribe for more