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The Art of Failure

Updated: Jul 26

I like to think of failure as an art. Because I believe that if done correctly, failure can be our greatest teacher. I also believe that people need to be given the space to fail. Space to embrace failure, and to learn from it. We spend way too much time trying to avoid failure. We treat failure like an ugly, shameful act. We see it as the opposite of success. When, doing nothing is the opposite of success. Failure is just another outcome of trying. And it can teach us so much on our journey in life.

Think back to when you were a child. Young and curious, excited to try things. What would happen if you didn’t get it right the first time? Did you have a parent, grandparent, sibling, or other loved one there as you tried new things? Did they encourage you to keep trying? Did they create a safe space for you to fail? Did this safety net allow you to learn from your failures?

There was an art to failure as a child. We were safe to try things, get them wrong, and try again. Nobody pressured us to have the answers and do it right the first time.

After all, we were just kids, and kids got to play, experiment, and given the grace to fail and learn. As we got older, things began to change. Our safety net shrunk, and we became fearful of taking risks without the guarantee of success. School got harder, college was more serious, jobs became demanding with even more pressure. As we grew, so did the stakes of getting it wrong the first time. Suddenly, a cost was associated with failure. And so, we raised expectations of ourselves to avoid that cost.

We also started paying attention to what society defined as success. That rarely included the try, fail, try again method from our childhood. It usually included tangible things like money, cars, impressive jobs, or milestones such as a marriage and/or children. Success focused more on the destination – and reaching it as fast as possible, rather than celebrating a bumpy learning journey. Society’s depiction of success has a lot of different standards – many of them are unattainable and unrealistic. There is no room for error if you want to be successful by society’s standards.

So, failure becomes a barrier to success. It slows the process. It becomes the enemy. But failure is not an enemy. Failure is still that beautiful learning lesson from our childhood. Failure is an art. And a necessity for success. I want to tell you how the fear of failure brought me to a perceived success, and how I left it all behind to pursue failure as an art.

Today I have been a founder of a total of four companies. I am the current CEO of one (technically two). You will not see them on the NYSE. You will not see me doing podcasts on how to replicate my success. They are small and each represents something I am passionate about. I grow them at a pace I am comfortable with. And I stretch myself, try something new, and learn from that every time. Sometimes I want to go faster than I am. But I force myself to slow down and sit in the ways I may be doing things wrong. It is exactly where I need to be.

That wasn’t my story a few years ago. Back then I was an executive leader. I was in one of three master’s programs. I was raising my kids on my own. I was patting myself on the back for all my accomplishments. In my mind, I was doing more than the average person and yielding higher than average results. But I was clueless.

In my job, I had no room for failure. I was a leader at a company that had been through a lot of change. My boss tasked me with to oversee even more change. I was brought in because I got things done and I rarely failed at it. But that environment didn’t work for me.

Previously, I had been given a space to experiment, design, and test large scale work. Like the safe space we remember as children – but with grown up ideas- I liked it and was good at it.

But this new space expected results all the time. I had a team that supported me.

And they had teams. How do you think it would look if I didn’t have space to fail? I tried as hard as I could to give them the space that I believed was important. To try, and learn, and try again. But when I had unrealistic timelines and stresses, I passed it down to them too. When I hadn’t checked my own high expectations at the door, I imposed them on my team. And that behavior carried itself down the line.

If I had my name on something and it failed, I was often asked for explanations. I was asked who on my team was responsible, and what I would do about it. Failure became a barrier to my success. I tried everything I could to avoid failure. I gave it no space in my life. Not in my work, not in my school, I even avoided relationships because I was convinced, they would fail due to my busy life. I was miserable, and so were plenty of others around me. But on the outside- I looked like a success to many. And by society’s standards, I was a success.

Three years ago, I decided to make a change. I could no longer sustain the life I had created. I had my own business 10 years prior and really enjoyed it. I had always dreamed of getting back to it one day. I also knew how I wanted to run a business and how I wanted to treat others. I wasn’t living out my own values and knew I had to leave. So, I took a big leap and allowed myself the space to fail. I started one of my companies while I was still working. I shared my mission with everyone who would listen.

When I realized I was living a double life by still working in a situation that was a contradiction to my values, I left. I knew I could fail big. I knew that failure had huge consequences. But I also knew my entire being relied on me living out my values.

I put 100% of my time into my first business six months after I started it. I had no guarantees. But I felt peace. And a safe space to try, fail, and try again. And I surprisingly had a large network of people willing to help.

Today looks very different than where I was just a few years ago. I will say, I have made many failures. But I have surrounded myself with others who offer a great deal of support. My quest for perfection is long gone. I wish I had figured that out before I went to three different master’s programs. Luckily, I only graduated from one. I am also happily married, and I practice the art of failure in that dynamic as well. I welcome failure daily. To me, that means I am living! I am trying things. I am growing and I am thriving.

There are four key components to my own art of failing that continue to serve me well.

1. Prepare, don’t control

I go into every situation knowing there is a chance for failure. It is my acceptance. I don’t try to anticipate the failure or control the outcome. I just remind myself that I may not be 100% successful. If my failure will impact others (a client, a partner), we discuss what a potential failure will look like, and we plan for that. Sometimes it is a contingency plan for a timeline being extended. Sometimes it is me not being able to make dinner as planned.

When I have honest discussion about what could happen, I don’t see myself as failing. I see it as life happening.

2. Mindfulness/Perspective

When I do miss a deadline or dinner or something else that I perceived as “failed”, I address it in the moment. I acknowledge the emotion in the moment, whether it is frustration or disappointment and validate it. Sometimes that is all I have time for in the moment.

Other times, I ask myself what is truly driving that emotion. Is it my expectations getting too high again? Is it a self-imposed depiction of success that I have not achieved? I gather what the perspective was that caused the emotion.

3. Reframe

I remind myself that success is individual. It’s personal. I revisit my own definitions. I revisit my values and goals. I reframe what I considered a failure into a learning opportunity.

4. Learn

I figure out what things did not go according to plan. I ask myself why. I separate what is in my control to do differently, and what is simply out of control. For example- if a timeline was delayed because a natural disaster shut everything down – not much in anyone’s control. I acknowledge it and move on. Things I can control- I brainstorm and get creative! I have fun with trying out different ways of doing things. I have a deeply analytical mind, so I see this practice like the scientific method, or PDSA for those improvement folk out there.

That is it. I follow a simple process for turning my perceived failure into art. I have no shame associated with failure these days. I welcome it. I still find that I take on more than I think is sustainable. I am still adjusting to this space and balancing it. But I have a completely safe space to learn.

Work and home are no longer separate. I don’t feel like an imposter, pretending that I have all the answers. I feel closer to the childhood days of experimenting. But with a lot more wisdom as I try things. So, remember these two things; 1. Failure is not an enemy, it is an art. It is a critical part of our journey towards success, not the opposite of it. It is how we learn best. 2. Failure needs a safe space to be the most effective in our lives. Don’t be afraid to ask for that space or create one yourself. You can’t appreciate failure properly if you don’t give it space. And if you lead others, please recognize the importance of creating a safe space to let people fail.

Now, please go fail beautifully.

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