Why can failure be such a powerful place to learn?
Some of the most powerful lessons in a career come from the work that did not go the way we wanted it to.
I would even go so far as to say that reflecting on failure can be one of the things that accelerates someone’s career. The important part is the actual reflection: taking time to understand what happened and then allowing it to change how you approach your work in the future.
That is part of what I mean by treating your career as a craft. You develop an understanding of why you do things a certain way, and you keep refining that understanding through experience.
And while I think failure can give you something significant to work with, I know it can also be a very painful place to reflect from.
Especially when a failed project feels like evidence that you, as a person, are a failure.
It’s one of the reasons we often avoid reflecting on our failures.
Does a failed project mean I failed as a person?
The failure of a project is the failure of a project. It does not reduce your worth or value as a human being.
When our identity and career become tightly fused, that distinction can be difficult to hold onto. We start interpreting what happens at work as a judgment on who we are. A project goes wrong and suddenly we are questioning our value instead of examining the work.
If that feels familiar, my Identity course inside Innervates explores how to begin separating who you are from the work you do. That separation gives you a little more space around you so you can actually reflect on what’s happening.
You can recognize a mistake you made without turning it into a verdict on yourself. Imagine what that would feel like!
Because even if you did actually make a mistake, my first question is always: what were the conditions around this project that set up the failure to happen?
Was it set up to succeed? Did you have the tools, training, support, and authority you needed? Did the organization accept the work, or did the systems around it prevent the work from taking hold?
It doesn’t mean we can always remove responsibility on ourselves, especially if it’s a repeat failure.
What if someone made a mistake that harmed the business?
I want to share an example without getting into identifying details, because it involves a sensitive incident.
At a technology company where I worked, we experienced a significant loss of customer data from production. There were backups available for recovery, but it was a serious situation.
An engineer had been carrying out work they were supposed to be doing. In the process, they ran a script that somehow had way too much access without enough checks. And the worst case scenario happened. (this is also pre-AI doing weird stuff)
It would have been very easy to stop the explanation there: the engineer ran the script, the data was lost, therefore the engineer should be fired.
My pushback was about the conditions that made that possible. Why could one person’s action have that much reach without an appropriate check or protection? How had we allowed a mistake to become an incident of that scale? More importantly, which affected what I was specifically working on, why were we not able to recover faster?
The engineer had made a mistake. But the missing protections were a failure in the system around them.
Leadership acknowledged that. The person was not punished, and the company put checks in place to prevent the same kind of incident from happening again. That’s how it should be.
That is the perspective I bring to failure. When an individual mistake can cause substantial harm, I want to understand why the organization allowed that mistake to have such a significant impact.
I am talking here primarily about people doing the work within a system. Leadership decisions about strategy, resources, and the design of that system involve a different level of responsibility.
My instinct is that very few workplace failures can be understood adequately by pointing at one individual and ending the investigation. A mistake still deserves attention, but so do the conditions that allowed it to happen or made its consequences worse.
How do I reflect on my own decisions?
Once you have some space from the personal judgment, look at the choices that were within your control or that you had meaningful influence over.
Write down the important decisions you made. Then ask why you made each one.
What did you understand at the time? What did you assume? What had worked for you before? What information did you have and what information did you not realize you needed?
The goal is to understand the thinking that produced the decision. Simply writing “I made the wrong call” does not tell you much about how to approach the next situation.
This is where reflection becomes part of developing your craft.
The important parts in the reflections are the UNDERLYING reasons. You’ll almost never find yourself in the same conditions again that caused the mistake to happen, but a similar mistake is still very very possible if we don’t learn why it happened this time.
Perhaps an approach you have relied on works well in one context but does not work in another. Perhaps you assumed a resource would be available, or that somebody’s agreement meant they were ready to act. Perhaps you did not have the support needed to carry out the work safely or successfully.
You want to understand which of those things was happening before deciding what needs to change.
What should I update in my approach?
I often talk about a mental model, framework, or craft playbook. In plain language, that is your understanding of how the work works: what you look for, what you expect, and how you decide what to do.
After a failure, ask whether that understanding needs an update.
Sometimes you need to change a step in your process. Sometimes you need to test an assumption earlier. Sometimes the approach itself is useful, but you need to recognize the conditions in which it will not work.
A difficult experience does not always mean you should abandon an approach entirely. It may teach you to notice a signal that you previously overlooked.
Try capturing the reflection in four short notes:
- The decision: What did I do, and what was within my control?
- The reasoning: Why did that make sense to me at the time?
- The lesson: What did the outcome reveal about my approach or the conditions it depends on?
- The update: What will I check, change, or raise with someone earlier next time?
Be specific enough that your future self could use what you have written. “Be more careful” gives you very little direction, but naming the assumption you need to verify or the condition you need to look for gives you something you can act on.
Some changes will be yours to make. Others will require support or changes from the organization. Recognizing that difference is part of the same learning.
How does this help me grow my craft?
The experience becomes useful when it changes your judgment.
Imagine two people with otherwise similar professional experience. One has encountered a difficult failure, examined their thinking, and learned to recognize a risk the other has not yet encountered. That experience may allow them to ask a better question or identify a problem earlier in future work.
That is one reason I see hard-earned lessons as part of the value of experience. When I think about what someone can bring to a team, I care about what they have learned and how that learning influences their decisions.
This reflection can also help you prepare for an interview. You will have a clearer explanation of what happened, what you learned, and how your approach has developed. We will explore that application more in the career change articles.
For now, the useful question is what you are taking forward into your work.
A failed project can leave you with a more developed understanding of your craft: where your approach works, where it needs to change, and what you need to notice sooner. Taking time to build that understanding is how a painful experience can become something that helps you do better work.
