The Art of Failing: It’s Never Too Late to Start

Failure Is Not the Opposite of Success

From the moment we are born, society talks about setting people up for success. What if we started setting ourselves up for failure? Learning how to fail is a fundamental part of life. Whether that be learning how to fail at baking a cake, failing to tie our shoes, or failing at remembering our passwords. As kids, we fail time and time again trying to crawl, walk, or speak. Without the inhibitions that we later learn to adopt in life, we continue, day in and day out, to fail. So, where does fear of failure come from? As we start to get older, the messaging changes. When we start to fail in school, we’re criticized for our bad grades, some even fear being expelled or dropping out. When we start to fail at work, we fear losing our job. And when we fail in relationships, we fear to be alone. Society has little grace for those who fail within the systems we have established. It imposes a rigid timeline for achieving major life milestones – secure a well-paying job, buy a house, and perhaps even find a partner and have kids – all by the age of 30. The rush to meet these benchmarks can prevent many of us from taking risks or trying new things later in life, fostering a fear of deviating from the established script.

But, what would you do if money were no object? (I understand this is a luxury not many can entertain, but bear with me, it’s just a thought experiment.) Would you still be pursuing the very same things you are right now, or would your life look any different? How do you really enjoy spending your time? Some students might say we’d like to be painters, poets, or writers, but everybody knows you can’t earn any money that way. Another person might like to live an out of doors life and ride horses. When you finally get down to that thing that the individual really wants to do, I would say to them: Go do that and forget about the money, because if you think that money is the most important thing, you will waste your life. You’ll be doing things you don’t like doing just to… be doing things you don’t like doing. It’s important to consider what you desire.

Alan Watts, in his iconic speech, challenges us to reimagine our pursuits in life by removing financial constraints from the equation. He urges us to consider what we would truly love to do if societal pressures were not a concern. The majority of people often end up sticking to the conventional path in life. Watts’s philosophy invites us to shift our focus. By doing so, we might find that trying something new, and re-learning how to fail in a society that rewards picture-perfect ideals, might actually be the biggest reward – or success – of all. In a world driven by perfection and self-optimization, the fear of failure often casts shadows over our true ambitions and dreams.

The Ego’s Grip on Success and the Perfectionism Epidemic

Societal expectations play a significant role in shaping our fear of failure. From a young age, we are conditioned to strive for success and avoid mistakes at all costs. This conditioning is reinforced by educational systems that prioritize grades over critical and outside the box thinking, workplaces that reward results over effort, and media that glorifies overnight success stories. At the heart of this fear lies the ego, a concept explored in depth by the prominent 19th-century German philosopher, Friedrich Nietzsche. According to Nietzsche, the ego is a central part of our consciousness, a dynamic force shaping our thoughts, actions and interactions, shaping our perception of the world and our place within it. He argued that while a healthy ego is essential for navigating life and providing a sense of self and purpose, an inflated or overly sensitive ego can become a significant roadblock. The ego thrives on validation and fears anything that threatens its constructed image. This fear manifests in an aversion to failure, as failure is perceived as a direct attack on our self-worth.

Now, in our hyper-competitive, hyper-connected world, the ego’s grip on our desire for success and perfection is further tightened by the media and culture surrounding us. Bookshelves are lined with titles such as The 7 Habits of Highly Effective People and How to Become Successful Quickly. Our social media feeds are filled with 15-second videos of “Top 5 Secrets of CEOs,” “How to Retire Before 40,” and so on. Everywhere we turn, media shows us that the pursuit of status, wealth and possession, is the measure of a successful life. The result? A hidden epidemic of perfectionism. And if there is one thing perfectionists can’t stand – it’s failure. Paul Hewitt and Dr. Gordon Flett are psychologists who have dedicated their careers to researching exactly what effect this has on us and our ego. Their work shows how different forms of perfectionism, often rooted in a fear of failure and a need for ego validation, are rapidly increasing in parallel to the pressures of media and culture. They have observed the following three types of perfectionists:

Self-Oriented Perfectionism: This involves setting unrealistically high standards for oneself and striving relentlessly to meet them. While it can drive achievement, it often leads to self-criticism, fear of failure, and difficulty celebrating successes. This type of perfectionism exemplifies the ego-driven fear of not measuring up.

Socially Prescribed Perfectionism: This stems from the belief that others have impossibly high expectations of us and that our worth depends on meeting them. It can lead to anxiety, burnout, and a fear of social judgment. This is exemplified by the illusion of perfection often portrayed on social media.

Other-Oriented Perfectionism: This involves setting unrealistic standards for others and becoming critical when they don’t meet them. It can damage relationships and create a sense of dissatisfaction. This type of perfectionism highlights the outward expression of an ego fixated on control and judgment.

Upon researching this, I found I could identify on different levels with each type of perfectionist. Hewitt and Flett’s work reveals that people aren’t either perfectionists or not, but rather, increasingly, the majority of us can relate to one or multiple of these personas on one end of the spectrum or the other. Meaning, most of us have a certain amount of fear of failure.

In the book The Perfectionist Trap, author Thomas Curran says: “Every last one of us in the West lives inside a culture knotted by perfectionistic fantasies. Like a holographic simulation of exaggerated reality, it’s a place where images and moving pictures of perfect lives and lifestyles beam from billboards, movie screens, television sets, commercials, and social media feeds. Within the hologram, particles of unreality fire indiscriminately. Each one teaches us that we’d lead a happy and successful life if only we were perfect.” Curran goes on to explain that we have achieved a hustle-and-grind culture so extreme that by being connected 24 hours a day, our egos are constantly being confronted and our self-worth questioned. These unattainable ideals push our egos to the point where we feel like we will never be enough. “Society’s expectations are well beyond the capacity of most people to meet,” says Curran, “Perfectionism isn’t about perfecting things or tasks, nor is it about striving for especially high standards. It’s about perfecting our imperfect selves; going through life on the defensive, concealing every last blemish, flaw, and shortcoming from those around us.” As Nietzsche reminds us, this is what leads us to our fear of failure. Perfectionists – which, to some degree, is almost all of us – are plagued by this as their sense of self-worth depends on the outcome of their efforts. This prevents them from even attempting tasks where success is uncertain as a radical act of self-preservation.

Reframing Failure and Why It’s Never Too Late to Start

What if we were to reframe our relationship with failure? What if, instead of viewing it as an attack on our self-worth, we saw it as the key to achieving what we truly desire? We have all heard the underdog stories of well-known creatives and celebrities who did indeed manage to overcome failure time and time again. Marilyn Monroe faced numerous rejections and setbacks in her early career. Despite these obstacles, she persevered, redefining herself and ultimately becoming an iconic figure in the entertainment industry. J.K. Rowling’s first Harry Potter book was rejected by 12 different publishers before she became one of the best-selling authors of all time. Vincent Van Gogh only sold one painting during his lifetime and despite the fact he never lived to see what impact his work would have on the art world, he is now considered one of the most influential artists in history. Vera Wang, after failing to make the US Olympic figure skating team, ventured into fashion design in her forties. Anna Wintour was fired from her junior role at Harper’s Bazaar early in her career, only to rise to the top of Vogue as editor-in-chief, becoming a legendary figure in the fashion world. Walt Disney was fired from a newspaper job for “lacking imagination and having no good ideas.” He went on to create an empire of animation and entertainment. It must be said that all of these people grew up in a time before the pressure of constant connectivity and social media, but their stories serve as a reminder that it is never too late to relearn the art of failing in life and start pursuing what matters most to you.

It’s easy to fall into the trap of thinking that certain dreams in life have an expiration date. The philosopher Epictetus once said, “One cannot learn that which one thinks one already knows.” If we stop daring to fail, we will never grow. Remember those early years when falling down was just a precursor to getting back up and trying again, undeterred? In today’s hyper-connected world, where the fear of failure is constantly magnified, it’s easy to lose sight of the lessons we once intuitively taught ourselves. Instead of chasing someone else’s definition of success, it’s time we start setting ourselves up for failure. As Alan Watts suggested, just ask yourself: What would you do if money were no object, if you didn’t fear to fail?