This is how to not fail at failing

Failing is a normal part of life. Here’s how to really learn from failure without fetishizing it.

This is how to not fail at failing
[Photo: IPGGutenbergUKLtd/iStock]

On November 10, 2019, I created a personal Slack channel for my company, LifeLabs Learning, to lose 10 pounds by the end of the year. The message:


“This is the 10 lb challenge! It’s conceited and hardcore. You ready?”

Around 20% of the organization ended up joining the challenge (including one of our CEOs). Every week, members weighed in, starting at 10 pounds (if someone lost two pounds, they would weigh in at eight). The goal was to get to zero.

Throughout our time together, we sent notes and pictures of encouragement and shared tips for success. We even named the group The Lightweights. But in the end, we all failed to reach that goal.


Investigating the failure

Since one of our core values at LifeLabs Learning is to “Always be Learning,” I asked the group why we came up short. The following were some of their hypotheses:

  • Doing it during the holidays was wishful thinking on my part.
  • I didn’t tether the goal to a bigger “why.”
  • I put zero structures in place to make it happen.
  • I let myself off the hook way too easily.
  • I didn’t hold myself accountable (or ask to be held accountable).
  • Doing it while visiting my parents was too much emotional labor.
  • I ended up focusing too much on the shiny extrinsic goal.
  • I didn’t plan my workouts.

These are all classic mistakes, but there is also something extraordinary about them. What most of these insights have in common is that they take ownership of the failure. This practice goes against our all-too-human tendency to blame mistakes on external events or people. The good news is that research shows that people who take ownership of their mistakes are more likely to learn from them.

Why is learning from failure so rare and difficult?

To fail at something is to (potentially) demonstrate incompetence. The cost, at least in our minds, is often catastrophic (loss of a job, relationship, respect, etc.). As human beings, we have a natural aversion toward loss. As a result, we approach the possibility of failure with trepidation (the technical term for this fear is atychiphobia). Studies show our bodies register failure as pain.


Failure also runs against the grain of our self-esteem. To fail at something means entertaining the possibility that perhaps we’re not as great as we’d like to believe. It’s not by accident that most people tend to attribute success to their efforts, while failure to circumstance. This bias, also known as the Fundamental Attribution Error, often obstructs people from gleaning lessons from their mistakes.

Most work environments don’t help much either. Organizations that are hyper-focused on end results have a low tolerance for experimentation and provide little time for reflection end up creating hostile conditions for learning. So what do we need to do to stop failing at failing?

1. Normalize it

In his book, Never Stop Learning: Stay Relevant, Reinvent Yourself, and Thrive, Bradley Staats argues that the key to learning from mistakes is to destigmatize failure. This means recognizing that failure is a normal (and at times, healthy) consequence of working in a complex environment.


At LifeLabs Learning, we normalize failure for our team by explicitly acknowledging the value of failure in our candidate interviews, during onboarding, and in our weekly team meetings. And in manager training we do for our clients, we normalize failure with workshop participants by calling it a critical part of the learning cycle.

2. Air it out

In Italy, there is a saying that a fish on top of the table stinks less than one under it. Put your failures (fish) on top of the proverbial table, and let the air circulate. Research shows that learning about other people’s struggles improves performance.

At Torres Wine Vineyard, for example, employees are required to inscribe their mistakes in a Black Book. As part of the onboarding process, there is a requirement for new recruits to read the book and internalize its message—we make and take ownership of our mistakes.


3. Be a failure role model

Airing your mistakes is effective because people often learn best through social modeling. As author Daniel Coyle has written, “No signal is so powerful as a leader who is open about their own mistakes.” In our research on what makes great managers, we’ve seen the same phenomenon. A great example comes from Nobel Laureate Frances Arnold, who recently tweeted:

“For my first work-related tweet of 2020, I am totally bummed to announce that we have retracted last year’s paper on enzymatic synthesis of beta-lactams. The work has not been reproducible. It is painful to admit, but important to do so. I apologize to all. I was a bit busy when this was submitted, and did not do my job well.”

Arnold’s tweet led to hundreds of comments, including fellow scientists congratulating her for publicly and courageously admitting her mistake.


4. Create a safe environment

Studies show that the best-run hospitals report 10 times more errors than their less effective counterparts. The key differentiator of great hospitals (and workplaces) is a climate of psychological safety— where employees can share perspectives and report mistakes without fearing censure or termination. Some practical ways to generate psychological safety include adopting values centered around learning and transparency. Other suggestions include implementing processes aimed at uncovering errors (e.g., after-action reviews, postmortems, etc.), and teaching leaders to acknowledge their own fallibility.

Saying there’s value in learning from mistakes doesn’t mean that we fetishize failure. It means that we understand that failing is an inevitable part of our fast-paced, ever-changing, and complicated working life. Those who can succeed at failing will triumph in the age of lifelong learning we now find ourselves in.

Next time you do something challenging, don’t ask yourself, “Will I fail? Instead, ask yourself, “How will I learn from my failures?”


Roi Ben-Yehuda is a trainer at LifeLabs Learning where he helps people at innovative companies (like Squarespace, Tumblr, Venmo, WeWork, and Warby Parker) master life’s most useful skills. You can follow him on Twitter.