How to Fail Intelligently

This post is excerpted from Issue #9 of The Shed, where we discuss the tools we use to tell stories. Subscribe to our weekly newsletter and read our archives on TinyLetter and Medium.

Failing Successfully: A Guide


What do we mean when we use the word “failure”? That’s part of the problem — failure isn’t one-size-fits-all, yet we often talk about it as if it were.

“Nobody would be in favor of an entrepreneurial failure that anybody with any insight or experience could’ve told you at the outset wasn’t going to work because it didn’t make sense,” Amy C. Edmondson, the Novartis Professor of Leadership and Management at the Harvard Business School, told us in a phone interview. “Starting a new company in a new setting with a promising idea — that’s smart, and it should be applauded […] But that’s different than a failure that anybody could’ve seen a mile away.”

The key, according to Edmondson, is to know the distinctions between three categories of failures:

1) preventable failures in predictable operations,

2) unavoidable failures in complex systems, and

3) intelligent failures at the frontier.

The first kind is not great 👎; the second is inevitable, but needs to be managed to avoid snowballing consequences; and the third is considered good 👍🏽 because intelligent failures “provide valuable new knowledge that can help an organization leap ahead of the competition and ensure its future growth,” Edmondson wrote in Harvard Business Review. That’s what leads to fresh discoveries, innovative products, radical businesses, and brand-new markets.

But even outside of the hierarchy of the organized workplace, we should all strive to create intelligent failures in our individual lives, whether that’s in the pursuit of a new career, a new fitness goal, a new state of mental health. Intelligent failures are how we make ourselves harder, better, stronger, faster.


Putting yourself out there can be terrifying (Lord knows, this Shed writer has a comfort zone about two inches wide), but sometimes you gotta risk it for the biscuit.

Individuals have to train themselves not to be so risk-averse that they don’t learn, stretch, grow, and possibly put themselves in a position to have the enormous upside of making a difference by succeeding in something that they think is slightly out of their reach,” Edmondson said. “It’s hard to implement it, but if you remind yourself that it’s where great successes come from, then you’re more willing to take that risk.”

That’s not to say that all the great success stories — for example, Thomas Edison, Michael Jordan, and others — recklessly set out to fail, Edmondson clarified. “It’s the combination of willingness to try and willingness to pursue something worthy. You don’t just wake up in the morning and think, ‘Hey, I think I’ll just go fail today.’ No, you say, ‘Hey, I think I’ll go after something important and worthy that may or may not work, but if it works, it’ll be awesome. But if it doesn’t work, I’ll learn a great deal from it that’ll help me go the next step.’”


You know the risks. You have one eye trained on success and one on intelligent failure. You’re ready to try your damndest. So what’s next?

According to Edmondson, you have to ask yourself a few things:

  1. What do I know?
  2. What do I not know that others know?

“You prepare yourself, get as much information as you can about what’s known, about the territory, and then you design your next move,” Edmondson explained. “Design is an important word because you’re thinking strategically, thoughtfully, systematically about what could really work well and what could pay off.

Luck is also a factor, true, but because we have no control over luck, it’s not a useful variable to fixate on. Instead, focus on what you can learn and do so you’ll have a fighting chance when venturing into new territory.


In organizations, according to HBR, pilot projects are usually designed to succeed rather than to fail intelligently in typical conditions. To know if you’ve put together a genuinely useful pilot that will produce valuable information even upon failure, the answers to the following questions should be affirmative:

“Is the pilot being tested under typical circumstances (rather than optimal conditions)?
Do the employees, customers, and resources represent the firm’s real operating environment?
Is the goal of the pilot to learn as much as possible (rather than to demonstrate the value of the proposed offering)?
Is the goal of learning well understood by all employees and managers?
Is it clear that compensation and performance reviews are not based on a successful outcome for the pilot?
Were explicit changes made as a result of the pilot test?”

Let’s apply this organization-oriented framework to a scenario from an individual’s everyday life: trying to get into the habit of writing and publishing online more often to build a bigger following on Medium.

Slay either way 🐝


Once you’ve failed with style 😎, it’s time for some self-reflection. Questions to ask yourself, according to Edmondson: “What happened? Why? What do I think were the contributing factors?” That might involve examining your own actions, getting insight from others, being critical and realistic.

“And then,” Edmondson explained, “having thought through what went wrong and why, you have a great deal more information for designing the next move — the next experiment.”

There are many ways to describe this kind of incremental assessment, attempts, and shifts to reach a larger goal: trial and error, proving a hypothesis, generating and testing, retrospectives, kaizen (h/t @bensheldon for suggestions). At the end of the day, it’s all part of a failure learning process that yields value when designed intelligently.

Now go get ’em, champ!

One More Thing

To further illustrate this framework, we made a game just for you:

Choose Your Own Adventure: Failure Edition ←

(We promise there’s only one ending with death in our version.)

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