Demystifying the fear of failure

Garrett Prince
Apr 23 · 7 min read
Zine by Garrett Prince & Andrew Richdale

Have you ever not done something at work because you were afraid to fail? I have. But, what is it about failure that induces this fear? Is it the thought of losing support from my lead, getting pulled from a project or even losing my job? Or, on a meta level am I afraid that my failures will define me?

After conversations with peers about failure, it turns out I am not the only one thinking about this. In fact, it seems like failure is actually quite mysterious, personal, and misunderstood given everyone’s unique relationship to it. While everyone had a different perspective, it was clear that someone’s fear of failure, or a lack of fear, could be the catalyst to their decision making. With this aversion to risk-taking we limit the projects we choose to tackle, our need for experimentation and we’ll likely have a harder time reaching any real breakthroughs due to fear.

Working at a company focused on innovation, our black ops design team became inspired to raise awareness to a topic as polarizing as failure in order to help shift our mindsets. But, in order to approach this problem we needed a simpler goal: get people to start understanding how fearing failure, instead of recognizing failure for what it is, can negatively affect our productivity and success.

With jobs in the tech industry, it’s often hard to step away and avoid time in front of a screen. Between being glued to our phones, using computers, and watching TV we absorb a majority of our content now behind glass. This is a rare and more recent phenomenon that will likely only get worse with time, and with such a saturation of digital content, what is the content that actually gets through to us?

In order to change people’s perception of failure, we knew a post or email would feel too familiar and get lost among the clutter. Instead, we leaned into a more tangible, yet risky, medium for our content — paper. We decided to print a short-form illustrated zine that examines failure through the emotions it evokes, aiming to spark more open dialogs about failure at Dropbox.

Failure Minded

These zines were made available to grab at people’s leisure, because we really wanted this experience to feel less prescriptive and more like a natural discovery. We didn’t want to tell anyone how they should react or force any modifications of behavior, but instead bring light to a concerning topic and arm people with a variety of relatable strategies to approach failure the next time it presented itself.

In the early stages of research for our zine, Failure Minded, it became clear that there’s a dichotomy around failure. On the one hand, people praise failure as a stepping stone on the road to success. On the other hand, some view failure as a crippling obstacle that must be averted at all costs. We wanted to try to understand the duality of this topic by exploring how this has affected successful people throughout history. If the people who we deem as successful also struggled with the same emotions we tie to failure, this could help provide comfort in knowing we’re all human and we’re not alone in our experience. This was also to prove a point that failure exists—it’s not something that needs to limit us or be an obstacle when setting our sights on big goals.

Archetypes of failure

To start our research process, I began reading articles about people throughout history who were considered failures. There was a lot of sifting through these articles to find quotes about failure, most of which felt cliché or were one-off examples that didn’t provide any real substance for this project. This was until I stumbled upon a quote from Michelangelo that really resonated with me:

The greater danger for most of us lies not in setting our aim too high and falling short, but in setting our aim too low and achieving our mark.

As a creative, Michelangelo fascinates me. I remember learning that when he was commissioned to paint the Sistine Chapel in Vatican City, he had little-to-no experience as an actual painter, which reminded me a lot of the concept of imposter syndrome.

Often in a creative field, when we take on larger and highly impactful projects, especially when navigating problems we may be unfamiliar with, we can feel we’re unequipped to do the job. I think some of us can also feel siloed and that we’re the only ones who might feel this way. I know I have.

After learning about Michelangelo, it was refreshing to know that someone who people idolize as one of the greats also had similar feelings as obstacles to his own success. In fact, he also often gave context to those he worked with that he lacked experience in certain artistic areas, just to avoid being labeled as a failure.

This example felt relatable, and helped me use this model as a launchpad to explore what other human symptoms might arise for people when presented with failure. As I continued, it became clear that some people’s emotional tendencies produce a negative effect, limiting their productivity, while other people actually lean into risk and failure for a more positive result!

In total, we were able to assign four concrete archetypes that felt most present and relatable when dealing with failure: The Imposter, The Saboteur, The Expressionist, and The Enthusiast.

  • The Imposter: Self-doubting, suspicious, driven
  • The Saboteur: Pessimistic, avoidant, cautious
  • The Expressionist: Unconventional, curious, determined
  • The Enthusiast: Supportive, empathetic, optimistic

Form and failure

Knowing this project referenced a lot of people preceding our time, I wanted it to feel classic and historical in presentation, which was why I chose to work with a vendor to produce a more traditional newspaper-print quality.

Type was also extremely important to me. A newer and more unique serif typeface for the title and main headlines promoted an elegant yet modern experience for the reader. This typeface also happened to be botanically influenced, with its lines relating to the growth of plants, which was an unexpected complement when thinking about how we’re trying to encourage growth and varied perspectives within the zine.

For the illustration work, I was inspired a lot by early surrealism and psychedelic design, specifically for the conceptual absurdity that a lot of this type of work possesses. This style of work feels experimental to me and represents altered states of mind, which felt perfect when thinking through the various emotions we can conjure out of fear. To me, failure, as well as topics like self-defining your own archetypes, can be deeply personal and not something people spend enough time exploring. I wanted each illustration piece to be a reflection of either the fears or the exciting unknowns associated with the process of risk-taking.

An opportunity to learn

Granted, we’re not sharing the bulk of content from our zine in this particular article, but we can share our most important learnings, which we find applicable to anyone who may be struggling with inactivity due to an irrational fear of failure. The first is to recognize that failure is 100% normal. It happens to us all! It’s a completely normal event for any team that is exploring a problem creatively and boldly. In fact, if you’re not failing, you’re probably not aiming high enough. Every failure is another opportunity to learn.

The second learning is when you fail, reflect. After any project, especially a failed one, meet with your teammates for a lightweight retrospective. During the retrospective, a team reflects on what happened in the iteration and identifies actions for improvement going forward. Ask each other honest questions and be candid. Record any learnings that could be applied to future projects on your team or other teams.

Finally, shifting our mindset on failure is a group effort. We’ve all developed certain behaviors around failure. Ask yourself how we can change these behaviors and shift our attitudes towards failure. By doing this, we’ll not only work together better, we’ll take the right risks we need to grow — both as individuals and as teams or companies.

Let’s be honest. In general, failure is misunderstood. The attempt of this entire analysis was only to scratch the surface and leave things more open-ended, to inspire others (you) to continue researching this and better help us all interpret our thoughts and opinions surrounding failure. As a creative, you’ve probably felt the pressures of delivering on a project with a risk that what you produce might not fulfill the desired needs of a client or team, and you’ll fail.

How do you navigate this experience and what are some ways you’ve learned to cope with the fear of failing? We’d love to hear from you.


Huge thanks to Andrew Richdale, John Saito, and Andrea Drugay for their writing guidance!

Want more from the Dropbox Design team? Follow our publication, Twitter, and Dribbble. Want to make magic together? We’re hiring!

Dropbox Design

We believe joy is the engine that powers all the best ideas. We’re designing an elegant and intuitive way of working, so you can love the way you work. More on https://dropbox.design.

Garrett Prince

Written by

Dropbox Design

We believe joy is the engine that powers all the best ideas. We’re designing an elegant and intuitive way of working, so you can love the way you work. More on https://dropbox.design.

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