Yes, It’s Great to Fail Fast!
- Mary
- Apr 11
- 5 min read
Updated: Apr 21
Guest Post by Jenni Jepsen
I remember back in 2nd grade, my teacher told my parents that I was a perfect student and a natural-born leader. (I got good grades and played well with others.)
Of course, I wanted to keep getting that kind of recognition and thus began my journey as a perfectionist.
I ruminated after making mistakes: “How could I have been so stupid to do that?” “Why didn’t I study more?” “Why didn’t I see that ahead of time, I could’ve done something!” Or so I thought. I didn’t know it, but I was hardwiring the reward of perfection in my brain. Failure was definitely not an option.
Do what? You want me and my team to fail fast?

The heart of failing fast: learning fast
Now, I don’t know about you, but I don’t want to fail, and I certainly don’t want to do it fast.
I needed to change how I thought about failing. When we try something and fail, we learn what works and what doesn’t as quickly as possible. I needed to reframe how I thought about failure. “Fail fast” is not failing, it is all about “learning fast.”
Still, as a recovering perfectionist, it’s hard to let go of old habits. I didn’t like showing people something that was not very good, or worse yet, might be a failure. It felt bad.
It’s true, we don’t like to look incompetent in front of others. Evaluation apprehension is a studied effect, showing that we feel anxiety when others evaluate what we do. We risk “losing face” in front of the people who matter most in the work that we do – our customers and stakeholders (not to mention any bosses that might also be in the room). The apprehension increases the likelihood that we will hold back or try to gloss over things that don’t work as well or look as good.
And when things do go wrong with what we’re showing to others – and things do – often “fail fast” thinking goes right out the window. Now, we have a problem. Good intentions for learning from what is not working the way we expected disappear when faced with the actual failure. Suddenly, we want to know how this could happen? Why isn’t it further along? Who’s fault is this? And how can we put procedures in place to assure this never happens again?
Placing blame gives us a feeling that we can somehow control or change what’s gone wrong. The interesting paradox is that taking responsibility for our mistakes, and more importantly, learning from them, is an indication of higher personal self-esteem. It increases our sense of personal control over the situation. Yet, we tend to point the finger in another direction, removing our own accountability.
The real issue is the meaning we attach to failure
The experiences we have had previously in our lives, where we worked before, or at home or at school informs how we react to the possibility of failing, making it difficult for our brains to distinguish between a good failure (learn fast) from a bad failure (one that we could have prevented – also a learning opportunity).
Leading psychological safety expert, Amy Edmondson has written extensively about failure. It’s the subject of her latest book Right Kind of Wrong. While Edmondson goes into more detail, I want to focus on two kinds of failure: preventable and intelligent.
Preventable failures – or mistakes – are things like forgetting to lock the door when you leave the house, not completing the final regulatory documentation before you release a product to your customers, surgeons who do a knee replacement on the wrong knee. These failures are preventable if we had just followed a checklist, or had someone remind us. Mistakes we can prevent up front.
Intelligent failures, on the other hand, are failures that we cannot know up front. In the work we do, we may have a hypothesis about a new product, feature, service, or solution of some kind, but there is no way of knowing if it will succeed until we get an early version out to people to test. That’s when we find out if we’re on the right track or not. If people hate it, or it doesn’t work, it fails. This essentially works the same way as scientific experiments. Scientists and researchers test things out, first in low-risk settings, to see what happens. Based on what they learn, they either move forward with another slightly higher risk test or drop the test and move onto something else.
Our brains are not helping us
It’s difficult for our brains to distinguish between the types of failures, unless we have been working with intelligent failures long enough for those to be recognized and categorized as “intelligent” in our memory. And while, we don’t want preventable failures, the failure happened. Blaming and punishing people for those failures activates our limbic systems – where our defense mechanisms are – and we go into flight, fight or freeze mode. We need to acknowledge those failures and learn from them, too. What can we fix to prevent it from happening again?
Intelligent failures have the biggest gap. Our initial reaction is negative (anger, frustration, disappointment, even disgust). To succeed, we need to view these failures as positive. Celebrate the early discovery that we need to pivot and do something else. We save our organizations time and money by learning fast. In fact, our competitive advantage today lies in how quickly we learn.

You can change your brain
By reframing how we think about failure and actively working to learn as fast as possible, over time we rewire our brains – building the positive connections related to intelligent failures. The learning becomes a reward in our brains. That means even recovering perfectionists like me feel good about failing and learning fast.
Tips to learn fast:
For people to embrace failing fast, we must cultivate a safe environment where we feel encouraged to speak up, share ideas, and take risks.
Embrace experimentation as a learning tool: Foster a culture where experimentation is valued not for the sake of failing but for the insights it provides. Small, low-risk trials allow people to gather data quickly and pivot based on real-world responses.
Implement rapid feedback mechanisms: Emphasize the importance of short feedback cycles. Regular check-ins and reviews – not just about outcomes, but about learnings – enable people to adapt promptly and refine their approaches based on collective insights.
Reflect on experiences: Create structured opportunities for reflection that allow people to focus on learning outcomes rather than failures. This could include after-action reviews or learning sessions that dissect different paths taken and their results, emphasizing growth rather than shortcomings.
Celebrate learning journeys: Shift your recognition systems to celebrate both successes and the learning derived from attempts. Highlighting how lessons learned contribute to future innovations fosters a culture eager to explore new ideas without the burdensome fear of failure.
Failing fast is not just a strategy, it’s a mindset that encourages innovation, engagement, and collaboration. As leaders, it is our responsibility to cultivate environments where ideas can flourish, and where learning is embedded in the culture. By fostering a landscape of safety, support, and shared ownership, we position ourselves to not only navigate failures but to transform them into our future successes.
Did you enjoy this article? Comment below and share your thoughts!
Thank you for sharing this insightful blog post on the concept of "failing fast." As a recovering perfectionist myself, I found the reflections both relatable and encouraging.
The journey from striving for perfection to embracing the idea of failing fast resonates deeply with me. Like you, I have often been caught in the cycle of self-criticism and fear of failure, constantly seeking to avoid mistakes at all costs. The notion of "failing fast" initially seemed counterintuitive and daunting, but the explanation of reframing failure as an opportunity for rapid learning has been enlightening.
The distinction between preventable and intelligent failures is particularly helpful. Understanding that some failures are inevitable and can lead to valuable insights has allowed me to approach…