Learning How to Fail Better Is the True Secret of Success

Mess-ups. Mistakes. Blunders. Whiffs. Screw-ups. Failures. We all experience them in various forms. The big. The small. The duh why did I do that? Deep down we know that learning from our failures is fundamental to success — it’s how we become better partners, better parents, better bosses, better people. But learning from failure also means sitting uncomfortably with our mistakes in an attempt to better understand what happened. That’s never easy, because facing failure requires us to confront things that can feel demeaning, embarrassing, and shameful.

“People have difficulty with failure,” says Dr. Laurence Weinzimmer, the Caterpillar Inc. Professor of Strategic Management at Bradley University and co-author of the 2012 book, The Wisdom of Failure: How to Learn the Tough Leadership Lessons Without Paying the Price. “We’re paid to succeed. We’re judged on our successes. We’re promoted on our successes. We’re rewarded for successes, and we’re penalized for failure. It’s a difficult topic.”

However difficult, learning how to better face and understand failure is a vital life skill. Who among us hasn’t reacted to a blunder by hiding from it, refusing to ask ourselves what went wrong — only to make the same mistake again? We’re likely all guilty of letting a small, embarrassing error grow bigger simply because we refused to acknowledge it in a healthy way. This isn’t uncommon, but it also isn’t useful. What actually is, per Weinzimmer: Developing the ability to reframe failure as a challenge — that is, an opportunity — rather than a personal flaw. That, and creating environments at work and at home where failure is seen for what it is — a step on the journey toward success. This isn’t some hidden truth; but it’s important to realize.

Fatherly spoke with Weinzimmer, who recently contributed to the book Work Life After Failure, about how to reframe failure, building resilience, and the importance of cultivating an environment where mistakes are met with curiosity, not shame.

Failure can be a difficult thing to face. It’s often easier to ignore it completely or not see it as a learning opportunity. Why do you think that is?

Well, people view failure as a negative. I’d say in the U.S., we’re probably more accepting of failure than other countries. But still in the US, failure is not viewed as something positive. I view failure as an opportunity. You have two choices when you fail. You can play victim and come up with reasons why you’ve failed, or you can thrive where it’s an opportunity to learn to grow so you don’t do it again.

When I was writing The Wisdom of Failure, I interviewed a lot of sitting CEOs. And I had one interview with the CEO of a Fortune 10 company. It was the best interview I had for the book. I flew home and the next day I got a phone call from him saying, “Larry, I decided I don’t want to be associated with this project.” And I said, “Why not?” And he said, “Well, because it’s too risky to have my name associated with a project on failure.”

So, I promised I would not use his name, but I can always use that story now. Ultimately, the majority of the CEOs I spoke to for the book are former CEOs. Because failure is not as big a stigma to them as it is with current CEOs. People have difficulty with failure. We’re paid to succeed. We’re judged on our successes. We’re promoted on our successes. We’re rewarded for successes, and we’re penalized for failure. It’s a difficult topic.

Sitting with and learning from failure is vital. We must look back and ask, “Okay, I did this wrong. Why did that happen?” But…that’s tough. How does one sit and think about failure effectively?

An important skill is the ability to reframe. I’m doing a lot of research right now on resilience, and it fits well with that. With resilience… when you’re faced with the challenge and you fail, if you view it as an impenetrable barrier, or if you view it as a personal flaw, it’s going to be difficult to grow from it. But if you view the challenge as an obstacle, and you don’t internalize it, you look at it as an opportunity. That type of reframe makes it [possible] to learn from failure, rather than be victim to it.

It’s about finding that space to look at failure and learn from it.

Absolutely. I’m big on doing a postmortem, whether it’s a success or a failure. Leadership has a long tail. You don’t know if you’ve made a good decision sometimes for years. But looking back, it’s important to ask, What did I do well? And keep doing that. As important is to ask, What didn’t I do well, and where can I improve? So, it’s really more of a reframe than anything else.

What should someone keep in mind as they try to reframe failure? What are certain things to think about or best practices to consider?

Well, let me put a caveat on it. There are different types of failures. Are there stupid mistakes? Absolutely. And I think if you make a stupid mistake, you must have a sense of humor about it. Laugh at yourself, figure out what you did, and avoid doing it in the future.

But if you make a big mistake, something substantive, rather than coming up with excuses for it, figure out ways to avoid it from ever happening again. The biggest failure is to make the same mistake over and over again. At that point, that’s a choice.

Fool me twice, as they say…

Yeah. People who don’t want to deal with failure just keep making the same mistake again and again. And that’s unfortunate.

It’s not uncommon for some to have a stubborn refusal to admit defeat. They think, Let me just try that again, because I don’t fail — something else has to have gone wrong.

Well, there’s this concept called hubris. It’s a personality flaw where you think you’re untouchable. You don’t make mistakes. In the last chapter of the book, I talk about self-absorbed leaders. And it’s a mix of hubris, arrogance, and narcissism. When you combine the three, those are the people who can’t admit to themselves that they make mistakes. And so, they do make those mistakes over and over. It really comes from a sense of low self-esteem, where they cannot admit failure to themselves.

You’re a parent, so I’m assuming you know that parenthood comes with plenty of mistakes. What’s important to remember about failure when you’re thrust into a situation where trial and error and getting a little bit better are a big part of the experience?

That perfection does not exist. People are messy. We all make mistakes. The most important thing to me is to be a good dad. And when I make mistakes and I have, I really think about what I could have done differently, I talk to my kids about it. We have frank conversations, where we say, “Hey, we went down this path and it probably wasn’t the most constructive thing. What do you need? What do you need to hear? What would’ve been better dialogue? Or what could I have done differently to be more supportive? Or to be better?”

As kids get older, you’re a thought partner with them. I think being vulnerable to your kids and letting them know Hey, I made a mistake, and what do you think about this? And how can we work together to make sure that doesn’t happen again? is very important.

That vulnerability can be tough. It’s easy to want to fix things.

That’s why I’ve made mistakes. Sometimes my kids have come to talk to me about something, and I immediately try to fix it. I’m in Dad mode. I need to fix it. And all they need is to have me just sit with them and listen. And so then, I think, Yeah, being a parent is tough.

Resisting the impulse to fix things is important.

Yes, and so is self-awareness. Let me go back to the question you asked earlier: Are there people that make the same mistakes over and over again? I talked about arrogance and hubris, but people that aren’t self-aware will make the same mistakes over and over again, too. And so to be self-aware, and be purposeful and trying to be a better dad is so critical to being a better dad.

Do you think that society-wise right now, Americans are, especially from a business standpoint, a little bit more open about their failures? It seems like every time I pop on LinkedIn, there’s someone professing about a mistake they made, and what they learned from it. This is obviously part of a certain performative work culture. But I was just curious if there’s anything that you had seen or learned about.

I don’t have any specific data on that, but anecdotally I have noticed people are much more open in talking about failure now than they have ever been. Usually, people are more open about failure when things are going well.

From a business standpoint, when I wrote this book, when I started doing the research on it, it was 2007, early 2008. This was before the bubble burst in the real estate market. And everybody was talking about failure. But once things got difficult, people stopped talking about it. They stopped admitting it. During good times, people are much more open at talking about failure. During difficult times, people tend not to highlight it as much. Because the consequences are bigger.

Resilience is a major part of learning about and adapting to failures. What are some things you’ve pinpointed that may be useful for the average person?

Well, I just published a chapter in a book called Work Life After Failure, which is all about how to bounce back after failing. There are two attributes to resilience. One is “trait resilience,” where we’re all hardwired in a certain way. Research shows people that are more adaptable, more optimistic and have a higher level of self-efficacy or belief they can succeed, tend to be more resilient.

The other attribute is called “state resilience,” which is “environmental resilience.” And if you’re in a situation where you can create a culture to allow people to thrive when they make mistakes, even somebody with low trait resilience can still be resilient if they’re in an environment of high-state resilience.

That’s very interesting.

In organizations, a big cultural attribute is something called “mistake tolerance.” We all make mistakes. And if you tolerate mistakes and allow employees to learn from mistakes, they can be more resilient. And same thing goes with parenting. You can create a family culture — knowing your kids are going to make mistakes, knowing they’re going to fail — where they’re not afraid to talk about it, and where they can objectively and constructively talk about it with you. So that they can grow from failures as well.

This article has been lightly edited and condensed.