A few years ago, I came away defeated and overwhelmed from an event I organized. I had spent months with the idea in my head. I had invested time and resources in making it happen. When it finally happened, it was a real disaster. I kept telling myself that the whole thing had been a complete failure and that word generated in me a sense of frustration, worry and enormous embarrassment. In my head there were a lot of fatalistic ideas and apocalyptic futures that never happened.

Leaving the location, I took a cab and opened Instagram looking for a distraction from my thoughts. The first thing that appeared on my timeline - as if the algorithm was reading my mind... well, isn't it - was a post by Renata Roa with a single phrase, the one with which John C. Maxwell's famous book is titled: "Sometimes you win, sometimes you learn".

And sometimes, I would add after that digital epiphany, all it takes is for the algorithm to work its magic for you to drop a few twenties.

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The power to fail

Some things have been said about failure, but I don't think I know anyone who has talked more about it than Pepe Villatoro, who I once heard him say on a mutual friend's podcast, Manuel del Vallethat "failure is information waiting to be attended. Information that you didn't have before".

I confess that I have that phrase written in my notebook of things and messages that I carry for life. So when I started to write these lines I did not hesitate to contact Pepe, an ardent entrepreneur and co-founder of FuckUp Nights, a project with which he has been talking for more than 12 years about the transformative power of failure as a learning tool.

Pepe, very generously, took my call and answered my questions.

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Why do you think failures hurt us?

At some point we bought into the idea that we can "be a failure". Failures hurt us because they touch deep fibers of our identity.

We live in a world that glorifies success and triumph, defined as being recognized by others and having more than others. In this society, failure becomes an antithesis to what we consider valuable. And we end up relating living a failure with being a person of little worth.

Every day we see people with simplified and made-up success stories in movies, social media and magazines. This creates a distortion in our expectation of what our life story should look like.  

It hurts because when we fail we feel that we are failing not only in our goals, but in who we are as people. That perception can be devastating, as failure challenges our beliefs about our capabilities and personal worth.

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What do you think is the impact on the mental health of people who undertake, the ideas we have about failure and success? And what are the burdens they generate?

The ideas we have about failure and success create overwhelming pressure.

On the one hand, companies are by definition a competitive environment and there will always be a company better or bigger than yours. On the other hand, it is said that a company that is not growing is dying (e.g., against inflation and competition). Those two forces added together generate a hamster wheel in which nothing is ever enough.

Many entrepreneurs get caught in a spiral of anxiety and self-criticism, where every goal not achieved becomes a confirmation of their worst fears.

We are specialists in suffering for what we imagine might happen, but hasn't and probably never will. We suffer for free.

The burdens are heavy: the need to add value 24/7, everyone's expectations and criticism, and the feeling of loneliness because you are the only person with that level of responsibility. Over time, this can lead to depression, burnout and an internal sense of scarcity.

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What do you think is the most damaging belief for entrepreneurship generated by ideas of failure?

The most damaging belief is undoubtedly the idea that failure is a reflection of a lack of ability or talent.

Success really depends mostly on our privilege: place of birth, family, health level, skin color, gender, whether we study or not and where, etc. Just because you don't have the same success as Leonardo DiCaprio, Elon Musk or Taylor Swift doesn't mean that you don't have the ability, or that you are a failure.

This belief can paralyze anyone, preventing us from experiencing, learning and growing.

Instead of seeing failure as an opportunity to learn and grow, it becomes a stigma that blocks creativity and motivation. This "all or nothing" mentality in which success is measured only by money, power, control over others or fame can lead many to abandon their dreams before giving them a real chance to flourish.

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What gift have your failures given you?

Two main gifts: character and self-confidence.

When I was younger I had doubts about myself because I had never experienced a very difficult situation. I doubted if I would be capable when something very ugly came into my life.

Then, over the course of a few years I lost everything financially, a corrupt boss forced me to lose my job and I lost my relationship with my biggest mentor and friend: my dad. Getting ahead helped me better understand who I am and what I am capable of.

My failures have taught me that I can live through difficult situations and come out ahead, being true to myself. Always living in line with my values and principles.

They have also taught me to live more in the present, to focus on what I can control and to take myself less seriously.

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What did I learn from all this?

At the beginning of November 2024, I had the opportunity to be part of a Wow Effect event with Liz Gilbertwho in her recent books and lectures has focused on talking about creativity and fear.

The idea that we have been taught about failure only generates fear, and fear is the main inhibitor of innovation and curiosity to experiment. With Liz we did an exercise where we saw that fears are not exclusive. If we identify our fears around failure and share them with someone else, we will realize that there is a lot in common and that those fears are less important than we think. Under this perspective, the opportunity opens up for a change of mindset, to create from another place, enjoying the process of seeing our ideas materialize and making them more robust thanks to the experiences we have had. This applies not only to entrepreneurship, but also to life itself.

In the talks I give on self-knowledge and my personal search for wellbeing, I talk about four stages to know ourselves and reconnect with ourselves. The relationship is very obvious: self-knowledge, from my point of view, is the basis of well-being and it is in this state that we open ourselves to creation. Now, if we transfer these four statements to those things that did not go as we had planned and through these we ask ourselves some questions, possibly the learning can be more visible.

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Let's try it.

- Question: What happened and why did it happen that way?
- Listen. Would the outcome have been different if I had done this or that?
- Reconnect. What decisions, beliefs and actions contributed to that outcome?
- Believe. Is there something concrete I can do at this moment and with this new information that will allow me to avoid repeating a similar situation?
This exercise can be done in a group or one-on-one. The more information obtained and the deeper the questions and answers, the more clarity there is likely to be.

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The event that was a complete disaster was not my first "failure" and not my last either. In my collection of "ideas that didn't work out as planned", there is a children's clothing brand, a bookstore, a shoe brand, a gastronomic project, a party/party in my adolescence and a couple of broken partnerships. In all of them I lost something: time, resources or people. But in all of them I learned a lot, about the markets I was creating, about new ways of running a project, about management, but mainly I learned about myself.

My failures have been a path to self-knowledge and this has triggered my curiosity to continue learning, experimenting and undertaking.

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Article published and extracted from Fast Company.

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