How to Ruthlessly "Fail" Like Sisyphus Every Day In Every Way and Never Internalize It

Today, I want to dive into a topic I’ve been grappling with for a decade: failure. Or rather, what we perceive as failure. If you’ve ever felt like you’re constantly pushing a boulder up a hill only to watch it roll back down, let’s talk about it if you’ve ever felt like you’re constantly pushing a boulder up a hill only to watch it roll back down about it. This one’s for you, fellow Sisyphus souls.

I want you to be like Sisyphus

We’ve all heard the myth: Sisyphus was condemned by the gods to roll a massive boulder up a hill, only for it to tumble down every time he reached the top. For many, this story is a metaphor for the endless grind of life. But what if we could flip the narrative?

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What if Sisyphus isn’t a symbol of futile struggle, but of radical acceptance? He never lets the inevitability of the boulder’s fall crush his spirit. He just keeps pushing, without internalizing the supposed “failure” of it rolling back down.

You won’t find Sisyphus in a therapist's office (for multiple reasons lol) talking about how he “feels like a failure” or thinks “I am a failure”.

That’s the kind of mindset I want to embrace….the kind I want you to embrace: to ruthlessly “fail” and yet never lose your sense of self-worth.

Sisyphus as a Revolutionary Symbol

Sisyphus’s story, as reimagined by Camus, resonates deeply with those seeking liberation. Imagine the absurdity of his struggle: rolling a boulder up a hill only to watch it roll back down. And yet, Sisyphus persists. He doesn’t resist or deny his reality. Instead, he embraces it, finding purpose and defiance in his labor.

For us, the boulder can symbolize systemic oppression, trauma, perfectionism, or even daily obstacles. Just like Sisyphus, we can stop fighting the idea of setbacks and instead view them as opportunities for growth. The key isn’t to avoid failure but to embrace it without shame. We can find purpose in the struggle, not because of its outcome, but because we choose to keep going.

“This is how we recognize the man who has tendencies toward an inner quest: he will set failure above any success, he will even seek it out, unconsciously of course. This is because failure, always essential, reveals us to ourselves, permits us to see ourselves as God sees us, whereas success distances us from what is most inward in ourselves and indeed in everything.” - Cioran

The Dance Between Success and Failure

“The Bhagavad-Gita tells us we have a right only to our labor, not to the fruits of our labor. All the warrior can give is his life; all the athlete can do is leave everything on the field.”

— Steven Pressfield

Western societies often define success as the goal and failure as the enemy. This mindset creates a binary rooted in colonial thinking; where success is glorified, and failure is feared. But what if they aren’t opposites? What if success and failure are interdependent, each providing wisdom that guides our paths?

Failure isn’t just a stumbling block; it’s part of the growth process. Every mistake teaches lessons, forces creativity, and allows us to try again. When we embrace failure as feedback rather than shame, we enter a cycle of evolution and experimentation. This is especially vital for those of us exploring intentional creativity and Afro-futurism, where imagination and reimagining futures are born through risk-taking, experimentation, and failure.

Decolonizing Success and Failure

Our culture is obsessed with achievement, and in that, failure has been demonized. Failure, especially for marginalized communities, isn’t just personal, it’s structural. Systems of oppression are designed to make individuals feel as though failing is evidence of personal inadequacy rather than the result of systemic inequities.

By rejecting these false narratives, we reclaim failure as collective learning. Failure can become a shared lesson rather than a solitary burden. Ubuntu, the African philosophy that says “I am because we are,” can teach us here. According to Ubuntu, failure isn’t just about personal missteps; it becomes an opportunity for collective support, growth, and compassion.

Failure is not a moral flaw; it’s a part of being human.

Why “Every Failure Is a Success” Falls Short

Saying "every failure is a success" is misleading and oversimplifies the complex reality of personal growth. While the idea may be well-intentioned, it often leads to toxic positivity by dismissing the real emotions tied to setbacks. Failure is valuable precisely because it highlights where we fell short, offering lessons that can drive future success. By redefining every failure as a success, we dilute the meaning of true achievements and risk missing the essential growth that comes from acknowledging mistakes. Instead of pretending failure is something it’s not, let’s embrace it as a source of feedback and reflection; key ingredients for genuine progress.

How Can You Be A Failure If Everyone is a Failure?

To redefine failure, we must first ask: who benefits from the way we currently view it? Colonial systems taught us to fear failure, equating it with laziness, incompetence, or lack of discipline. These narratives were designed to uphold oppressive hierarchies, where the success of a few relied on the perceived inferiority of the many.

But failure isn’t a moral flaw; it’s a natural part of growth. From an Afrocentric perspective, failure can be reframed as a collective lesson. The Ubuntu philosophy, “I am because we are”, teaches that when one of us stumbles, it’s an opportunity for the community to learn and support each other. Failure ceases to be a solitary burden and becomes an invitation to deepen our interdependence and compassion.

You Can Never “BE” A Failure or Anything At All

“Failure, to mean a person who has failed, is of fairly recent coinage. The Oxford English Dictionary dates it to only 1865. Before then, the historian Scott Sandage notes, the word was ‘an incident, not an identity’. A failure meant a business that had failed. Failure first became an identity, Sandage argues, in nineteenth-century America.” - Joe Moran, If You Should Fail

Similarly, the language of capitalism, branding people as “winners” or “losers”, reinforces this harmful framing. It assigns a fixed identity to what is, at most, a momentary state. You can fail at something without being a failure, just as you can succeed without being a success. We are always more than our latest outcomes.

You can’t be a failure and you can’t be anything at all because you are always changing and do not have a fixed sense of self, be careful to not confuse actions or events that are temporal, with your essence.

How Can You Be A Failure If Death is the Ultimate Failure?

The philosopher Heidegger proposed that we are beings-toward-death; a reality that highlights life’s impermanence. In a strange way, this puts all our small failures into perspective. If death is the ultimate failure (the one constant every human faces), our daily missteps lose their sting. Every setback becomes a reminder of life’s beauty, not despair, but freedom: freedom from needing perfection because life is inherently uncertain.

By embracing this truth, we can live authentically and fully without the pressure to control every outcome.

Decolonizing Our Relationship with Failure

Radical well-being asks us to examine how colonial systems have shaped our relationship with failure. Under capitalism, failure is often tied to productivity, performance, and profit. This framework reduces human worth to output, leaving little room for rest, recovery, or imperfection.

To decolonize our relationship with failure, we must embrace rest as a form of resistance. Rest disrupts the cycle of burnout and reclaims our right to exist beyond our achievements. By allowing ourselves to fail, and to pause without judgment, we create space for true healing and growth.

How to not take failure personally

Diversify

One of the most powerful ways to mitigate the sting of failure is by diversifying your pursuits. Our culture often idolizes the "Michael Phelps" approach; hyper-focused on one goal, career, or path until we master it. While dedication can be admirable, putting all your eggs in one basket creates a high-risk situation. If that single pursuit falters, it becomes much easier to wrap your entire identity around that failure, making it feel catastrophic.

But what if failure doesn’t have to feel so devastating? When you invest in multiple areas of your life, different passions, creative outlets, career paths, relationships, and dreams, you build a safety net for your identity. Failure in one pursuit doesn’t have to undo everything. Instead, it can simply become a lesson and a stepping stone, leaving your other areas untouched and thriving.

By embracing multiple goals, you create a holistic life where setbacks are seen as part of a much larger journey, not the end of it. You are more than any one success or failure because your identity isn’t anchored to a single pursuit. This perspective allows you to remain resilient, creative, and flexible. Your self-worth becomes rooted in the process rather than the outcome, allowing failure to become an opportunity instead of a crisis.

Diversification isn’t just about hedging your bets, it’s about embracing the fullness of life and all its possibilities. You can thrive without needing to achieve perfection in just one area. This approach allows freedom, creativity, and self-discovery while also protecting your heart and mind from the weight of tying your worth to a single, narrow pursuit.

Move to Level 3 Self Esteem

Dr. David Burns, the the author of one of my favorite books, Feeling Good, also has a pretty prolific blog where he expands on this idea of different levels of self esteem that he mentions in his book.

Level 1 is where most of the population is at, which is conditional self-esteem. (I am worthy only if X)

Level 2 is where a lot of people are at and often where they stay which is unconditional self-esteem. (I am worthy no matter what)

Level 3 is a paradigm shift likened to enlightenment. You suddenly see “self-esteem” as just another perfectionistic (and meaningless) verbal trap, a waste of time. You discover that “self-esteem” and “worthwhileness” are something you never needed in the first place. Just another burden, like the equally meaningless concept of a “self.” (Human beings either A. Have no worth at all, or B. Have one unit of worth from birth to death and nothing they do or don’t do can subtract or add to it. Whether you choose A or B, the fundamental result is the same).

Through therapy and self-love practices, you can likely get to level 2 or 3 if you prioritize it.

Once you move out of Level 1, your relationship with failure will change drastically and you’ll notice improvements.

Neurodivergence and Failure

For neurodivergent individuals, societal expectations often frame differences as failures. The systems we live in rarely accommodate diverse ways of thinking and being. But this reframing, seeing neurodivergence not as a deficiency but as adaptation, disrupts these narrow definitions of success and failure. Neurodivergence offers alternative ways to approach challenges creatively and authentically, teaching resilience by shifting perspectives.

You aren’t failing by diverging from rigid norms; you’re simply resisting systems that were never designed with you in mind.

Enlightenment and Failure

“Millions of people have spent their lives, and some have even lost their minds, trying to win enlightenment without ever comprehending, as they sucked their last breath, what it was they had gambled to get. Had they attained enlightenment without being aware of it? Are there stages of enlightenment (maybe, depending on the type of Buddhism to which one subscribes), and how far had they gotten?”

- Thomas Ligotti

“In his One Taste: Daily Reflections on Integral Spirituality, Ken Wilber, a widely known and highly influential multidisciplinary scholar and theorist of spiritual traditions, reported that he asked one Zen Buddhist master “how many truly enlightened — deeply enlightened — Japenese Zen masters there were alive today.” The master replied, “Not more than a dozen.” Another Zen master put the number of fully enlightened individuals in the East at one thousand throughout Zen Buddhism’s history. Wilber’s conclusion: “Thus, without in any way belittling the truly stunning contributions of the glorious Eastern traditions, the point is fairly straightforward: radical transformative spirituality is extremely rare, anywhere in history, and anywhere in the world. (The numbers for the West are even more depressing. I rest my case.)” - Thomas Ligotti

But what if enlightenment isn’t a destination, but a practice of failing with grace? To seek enlightenment is to fail daily, at letting go of ego, at embracing the present, at understanding the infinite; and yet, to persist. Spirituality, like life, is not about achieving perfection but about the beauty of striving imperfectly.

Careers, Capitalism, and Failure

“The radical therapist David Smail used the term ‘magical voluntarism’ to describe this fallacy that we can stop a dysfunctional world causing us distress purely through our own efforts. In magical voluntarism, the miserable must acclimatize themselves the the system that is making them miserable. All that happens is they become depressed. Depression is an internalized protest, a silent remonstration against reality. Instead of getting usefully angry with the way the world works, your mind berates itself. A success recedes further from your reach, you tell yourself that you just have to shake off your failure and try harder. Cruel optimism, indeed.”

— Joe Moran

“We are born dying, as Heidegger said. One way we protect ourselves from this distressing truth is with something called a career. The word career originally meant a racecourse or racetrack. Its source was the Latin carrus, for ‘wheeled vehicled’, from which also comes car. By extension, career came to mean a gallop, a swift course, rapid and continuous progress. The notion of a career as the course of one’s working life, with constant opportunities for advancement, did not fully develop until the early twentieth century. Our identities came to rest heavily on the paid work that we did. Anyone who had not turned their life into a career trajectory was now in danger of being seen as less of a citizen, a partial person — a failure.”

— Joe Moran

Trying to do “it all”, especially all at once, and falling face first because of it, is a good way to convince yourself that you are a failure. This is a very popular subliminal message that can lead to hustle culture and burnout. It can’t be the case that you must do more than you can do. You are a human being and not a machine. You will do what you can, you won’t do what you can’t, and the tyrannical inner voice telling you that you must do everything is simply mistaken. There’s no reason to believe you will ever feel “on top of things” or make time for everything that matters, simply by getting more done.

Redefining Failure in the Context of Liberation

Our society tends to view failure as an individual flaw, a marker of incompetence or inadequacy. This perspective, deeply rooted in White Supremacy Culture, upholds perfectionism and individualism while punishing mistakes. But for those of us invested in decolonization, failure demands reframing.

In a decolonized framework, failure is not a measure of self-worth. It’s a reflection of systems that prioritize hierarchy over humanity, conformity over creativity. For marginalized communities, failure often stems not from personal shortcomings but from systemic barriers.

By rejecting these oppressive narratives, we reclaim failure as a natural and necessary part of growth. It becomes a shared experience, a collective lesson, and a step toward self-mastery.

Mimetic Desire and Failure

Why do we fail at certain goals? René Girard’s theory of mimetic desire suggests that many of our aspirations aren’t even ours. We chase what others value, mistaking their desires for our own.

“We think we want the object, but actually we want the charismatic quality we assign to the rival who also wants or already possesses that object. Mimetic desire is asking for the impossible: for us to be someone else.” — Joe Moran

For Black and marginalized communities, this can look like striving to meet standards rooted in white supremacy or capitalist ideals. When we fail at these goals, the pain is amplified by the dissonance between what we’ve been taught to value and what we truly need.

When we fail at these borrowed dreams, the sting is sharper because it’s tied to validation rather than fulfillment. The antidote? Radical self-awareness. By identifying what truly matters to us, we can fail forward toward goals that align with our authentic selves.

Writers and Creatives are the biggest failures

“‘In the long run we are all dead.’ the novelist Anne Enright writes, ‘and none of us is Proust.’ Even successful authors see themselves as failures. Chekhov complained in his letters about railway bookstores not stocking his books. Henry James was a failed playwright, William Faulkner a failed poet. Paul Potts’s friend George Orwell saw his career as mostly wasted time and wrote in his essay ‘Why I Write’ that ‘every book is a failure’. When T. S. Eliot’s publisher, Robert Giroux, suggested to him that most editors are failed writers, he replied: ‘Perhaps, but so are most writers.’ Ezra Pound, interviewed by Allen Ginsberg near the end of his life, called his own work ‘a mess…stupidity and ignorance all the way through…I found out after seventy years I was not a lunatic but a moron.’ When Philip Roth gave up writing aged eighty, unable any more to stand the daily frustration, he said: ‘It’s just like baseball: you fail two-thirds of the time.’”

— Joe Moran

“Writing appears to be exempt from the 10,000 hours rule — that theory, with its suspiciously round number, which contends that the key to achieving expertise in any field is to practice the right way for long enough. In writing, no amount of work imparts mastery. Nor does worldly success offer indemnity against what Zadie Smith has called the ‘intimate side of literary failure’, the ways in which writers fail on their own private and singular terms. Smith imagines this land of literary failure as ‘mostly beach, with hopeful writers standing on the shoreline while their perfect novels pile up, over on the opposite coast, out of reach.’”

— Joe Moran

In the practice of intentional creativity, failure becomes a generative force. Artists, writers, and visionaries know that their best work often emerges from missteps. Toni Morrison described writing as “a process of discovery,” one where the initial drafts are rarely perfect but always instructive.

Afro-futurism offers a similar perspective, envisioning futures where Black people and cultures thrive despite the failures of the past and present. In this context, failure is not a dead end; it’s a pivot point. It’s the raw material from which we can build new, liberated possibilities.

Intentional creativity is a practice of using imagination and artistry to transform our understanding of the world. It invites us to engage with failure not as a limitation but as raw material for creation.

When we approach life creatively, failure becomes a canvas. Each misstep, rejection, or setback provides texture and depth to the masterpiece we are creating.

For the Afro-futurist, failure is also a gateway to imagining new possibilities. If we are not constrained by the fear of failing, we can dream bigger, explore further, and disrupt the status quo.

Final Thoughts: You Are Not Your Failures

“To call any life a failure, or a success, is to miss the infinite granularity, the inexhaustible miscellaneity, of all lives. Every, life is incommensurable with any other life. Someone else’s success does not make you more of a failure, because their life can never subsume or cancel out yours. Each life runs along its own tracks to its own destination. It can’t be compared to anything outside itself, nor judged by any yardstick other than its own. A life can’t really succeed or fail at all; it can only be lived.”

— Joe Moran

You are more than your successes and your failures. You are a complex, changing, evolving human being. Failure is not a fixed identity, it is temporary, it is feedback, and it is a catalyst for change. You are always growing, and as long as you keep pushing the boulder, you are resilient.

Like Sisyphus, you may find yourself climbing hills over and over, only to watch things roll back down. But remember this: the boulder itself isn’t the problem. It’s the journey, the effort, the process, and the dignity of trying.

Never internalize failure as an identity. Instead, embrace it as part of the process. Keep failing, keep growing, and know that liberation is not about perfection. It’s about persistence, creativity, and collective freedom.

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