The 5 Strange Truths Fernando Pessoa Brings To Business

Counter-intuitive wisdom from the business poet of Lisbon

The multiple identities of Fernando Pessoa

“There are serious matters in life to be learned from charlatans and bandits, there are philosophies to be gleaned from fools.” — The Book of Disquiet

The culture of business has become a cult of personality.

The likes of Steve Jobs, Elon Musk, Richard Branson, and Donald Trump are held up as prophets of profit. We are urged to model our work after theirs, with the expectation that we can become like them. As inspiring as the biographies of charismatic corporate leaders can be, they’re missing one powerful source of insight: The experience of despair and failure that is much more typical of experiences in business than the heroic victories of the moguls.

Ironically, those who have failed can teach us a great deal more about untapped opportunities for success than the successful can. Biographies of great business successes tend to tell us only about the opportunities that have already been tapped.

It’s time to think different — not by adoring Steve Jobs and buying Apple products, but by attending to the insights of those who have lived out on the edge of innovation. You can count Fernando Pessoa as one of their number.

Devoted in Disenchantment

— Max Weber

Fernando Pessoa never achieved much recognition during his lifetime. Only after his death in the 1930s did he gain attention as one of the most important writers of his time, not just in his home country of Portugal, but in all the world.

Pessoa wasn’t just a neglected writer, however. He also worked as a business clerk, translating professional documents. Rather than maintaining separate literary and commercial identites, he brought soulful attention to the world of commerce, struggling to find a place for human experience within the machinery of business that had expanded across the globe during his lifetime.

One of the reasons Pessoa’s words have endured is that they represent the unease which characterizes our experience of modern commercial culture. He gave voice to the pervasive feeling of alienation from the world created by business — a cultural schism that has arisen from the very success that business pursues.

From the National Museum of World Cultures

Those who are caught up in the confidence of business success can be blind to the influence of this disenchantment. So, Fernando Pessoa’s writings provide a much-needed counterpoint to those unrelentingly upbeat listicles about entrepreneurial drive that dominate popular business writing today (

You won’t read the following advice in the Harvard Business Review, but that’s part of what makes it worth listening to. When the world zigged, Fernando Pessoa zagged, yielding rich material for genuine differentiation to those who care to pay attention.

1. Embrace the Power of Stupidity

Fernando Pessoa did not lack for the basic physical needs of life. Yet, he longed for something more than that, for Pessoa was in search of the experience of stupidity.

Stupidity is not the same thing as idiocy. It isn’t the opposite of intelligence. Geniuses are capable of being stupid. Rather, stupidity is something beautifully different from intelligence. While intelligence relentlessly pursues the correct answer to a question, stupidity revels in the marvelous implications of a question.

The real meaning of stupidity becomes clear when one considers that the words “stupid” and “stupefy” share the same Proto Indo-European root word. That root word referred to the condition of being by something.

Being struck is what business is all about. Being successful in business depends on the ability to strike people, to make an impact. In business, the most intelligent thing to do is to grasp the power of stupidity. Pessoa observed,

While engineers build supercomputers capable of great feats of artificial intelligence, people continue to feel a hunger for an escape into experiences that have nothing to do with intelligence. As the world of machines demands accurate data, we respond by seeking an emotional truth.

Intelligence provides us with a remarkable breadth of knowledge. It brings us none of the motivation we need to apply that knowledge.

Hail to the Stupendous

If you need an example of the power of stupidity, just look to Donald Trump. This isn’t meant as an insult to Trump, who is quite intelligent in his own way. The point is not that is stupid, but that his approach to politics makes stupid.

Trump has gathered political power for himself by tapping into something completely other than intelligence. He didn’t win the 2016 election because of his command of facts. He doesn’t construct logical arguments to support his actions. Often, he doesn’t even bother to speak in complete sentences.

Instead, Trump regularly leaves Americans dumbstruck, gobsmacked, flabbergasted. Right or wrong, he disables our intellects, and gets right to the core of what makes us move.

Intelligence has its proper place in business, but being stupid isn’t something to be avoided. A business can’t accomplish great things without it. In fact, stupidity is essential to the greatest joys in life. That’s why people seek it out with such hunger. As Pessoa wrote,

Stupidity is stupendous.

2. Satisfy the Hunger for Inconvenience

In his collection of English sonnets, Pessoa wrote:

Like to a ship that storms urge on its course,

By its own trials our soul is surer made.

The very things that make the voyage worse

Do make it better; its peril is its aid.

And, as the storm drives from the storm, our heart

Within the peril disimperilled grows;

A port is near the more from port we part —

The port whereto our driven direction goes.

The message contained within these lines points in a different direction than the slick and easy minimalism beloved by most UX designers.

The linear problem-solving mindset that dominates business strategy supposes that the most reliable way to give people what they want is to ask them what they want, and then give it to them. The trouble with this approach is that people rarely say what they really want when they’re asked directly.

When surveys ask people to rate what they want out of a commercial experience, low cost and convenience typically rise to the top. In practice, however, consumers frequently spend money on products and services that are unnecessarily inconvenient and expensive. Why?

Devotee practicing ritual ordeal at Thaipusam, from William Cho

In the right circumstances, people aren’t happy in spite of inconvenience and expense. They achieve happiness of inconvenience and expense. In a series of experiments, Dmitris Xygalatas and Ronald Fischer discovered that, in the right context, suffering can bring about a special kind of satisfaction.

Fischer and Xygalatas compared the physiological and emotional states of participants in and observers of different ceremonial activities occurring as part of the Hindu festival of Thaipusam in the island nation of Mauritius. During the festival, people can choose between experiences that involve a relatively low level of ordeal (such as prayer and singing) and experiences that involve a high level of ordeal (such as walking on hot coals or sword blades, piercing the face and body, and dragging carts by cords attached to hooks embedded in the skin).

These ordeals were the opposite of convenience, but Fischer and Xygalatas found that at the end of their processions, the people who went through high ordeals actually reported feelings of greater happiness than those who merely prayed or sang. What’s more, the experiments revealed that the more difficult the ordeal that participants went through, the more money they were willing to give away to the sponsors of the ritual at the end of their experience.

This level of devotion is something few commercial brands have been able to elicit. Most brands, even those that are household names, inspire low levels of consumer engagement. Part of the reason for this consumer apathy is that marketers have been focusing on making the purchase and consumption of products cheaper and easier. It hasn’t occurred to them that they might profit by creating opportunities for consumers to suffer meaningly for their brands. Of course, it would be culturally inappropriate for marketers to ask consumers to pierce their cheeks, walk on hot coals, or go through rites of body modification to demonstrate their brand loyalty. The Mauritian experiments do suggest, however, that the creation of a meaningful context can help marketers get around the rationalizations of convenience and low price.

Certainly, consumers don’t want to experience arbitrary inconvenience. They’ll be frustrated by random obstacles. Suffering alone won’t contribute to an engaging consumer experience unless it is convincingly linked with a system of profound cultural significance. However, with some attention to cultural design, consumers will eagerly embrace commercial experiences that are anything but cheap, quick and easy. They are grateful for the opportunity to associate with brands that are worthy of their sacrifice.

3. Pursue Fluid Segmentation into Multiple Identities

No person can be reduced to one persona

Segmentation has become one of the primary tools of business. Companies spend massive amounts of money to profile existing and potential customers, trying to figure out which types of people are most likely to buy their products, and creating personas to represent those types. They reduce the complexity of people’s lives into a shallow caricature that fits on one page, often summarized with a cute, alliterative title like “Suzy Soccer Mom”, “Marketing Mary”, or “New User Ned”.

Digital technology has placed segmentation at the center of marketing innovation. As Big Data keeps on biggering and biggering, targeted advertising promises to send just the right message to just the right audience. We’re told that data analytics is making business more personalized, but without the trouble of personal interactions.

A little glimpse under the hood brings the boasts of personalization into considerable doubt. My own Twitter data profile, for example, suggests that Twitter is sending personalized advertisements to me based on the premise that I am both a grandfather and a grandmother. I have no grandchildren at all. Neither am I a “corporate mom”, a “fit mom”, or a “green mom”. I’m a dad.

How could an objective, data-driven profile based on years of concrete information about my actual behavior be so dramatically off-target?

The answer has to do with a basic misconception about human identity at the heart of most segmentation schemes: The assumption that human beings can be sorted, like objects, into static, enduring categories, from which our behavior can be reliably predicted.

As Todd Rose, author of The End Of Average and co-founder of the Center for Individual Opportunity explains, statistical models that sort people into types tend to do a great job of predicting the behavior of people in groups, but don’t do very well at predicting the behavior of actual individuals. Though the types developed through Big Data analytics are accurate descriptions of group dynamics, almost no one within the targeted groups closely match their segmentation. That’s why supposedly personalized business communications so often come off as impersonal.

Individual identity is much more complex than any quick data profile can reveal. One manifestation of this complexity is the multiplicity of identity. While consumer segmentation models typically presume that people can be defined as types that align with set routines of consistent behavior, people actually maintain many different identities, each with its own priorities and behavioral routines.

Photo by Alan King on Unsplash

Fernando Pessoa made the exploration of the many facets of his identity a lifelong quest, and in the process, he split himself into 73 pieces. (No, he didn’t use a horcrux.) Pessoa wrote under at least 73 different pen names, which he referred to as “heteronyms”: Alberto Caeiro, Ricardo Reis, Alvaro de Campos, Bernardo Soares… He regarded each one of these identities as real in their own way, rather than being mere pseudonyms. Each of his heteronyms had its own experiences, attitudes, and writing style.

People often wonder why Pessoa would fracture himself in such a way. Actually, the division of identity came naturally to him from the time he was a small boy, when he created his first heteronym. Pessoa wrote, “

Few of us manage as many identities as Pessoa did, but in our complex society, no one beyond the age of five gets by with a single, exclusively-authentic sense of self. We create different versions of ourselves to cope with the unique expectatons of different social settings and relationships. The identity we adopt at home is quite different from the identity that we exhibit at work. Like Fred Rogers, we change clothes, and shift our attitudes, when we walk through the door at the end of the day.

Mr. Rogers enters his Neighborhood identity

Although executives at tech companies demand that we adhere to policies of maintaining just one “true” identity, it’s becoming common practice to create multiple identities per platform, what Natasha Vita-More, editor of the Transhumanist Reader, refers to as “”. Each of these identities we create depicts a different aspect of the self for a different social context, so that, as a whole, we use social media to represent ourselves in mosaic form, refusing to limit ourselves to the stiff limitations of any single format.

The dynamics created by this mosaic sense of identity are important for businesses to consider, because until companies understand who they are selling to, they can’t craft relevant business strategies. Identity is the landscape within which all commerce takes place, but it’s a weird landscape, more like the quantum world than the flat maps crafted by the cartographers of data.

This idea is explored by Helene Lundbye Petersen, an artist-in-residence at the House of Beautiful Business, who points out that

Simplistic segmentations enable businesses to grasp only obvious opportunities. Instead of segmenting the marketplace into static types, businesses can profit from recognizing the segmented selves that exist within each of us. Alongside their attempts to corner us into predictable routines, businesses can begin to explore the processes through which we change, shifting from identity to identity. We buy what we buy, after all, not just because of who we are, but also because of who we want to become.

As Pessoa advised, It is in those transitional spaces where we are open to change that the greatest enterprises begin.

Just a few of the 100 gender identities listed by Gender.Wiki

As digital technologies disrupt traditional social relationships, our cultivation of multiple identities is only growing more difficult to track. Once we begin to cultivate different aspects of ourselves, we let go of the notion that there is a true self, and the nature of truth itself grows soft around the edges.

The Post-Truth world didn’t begin with the election of Donald Trump. It has been in development for generations, a cultural accompaniment to the general relativity of physics. Back in the 1930s, Pessoa described his own sense of self-estrangement, writing,

Like electrons forced to locate themselves through the influence of observation, people will present data miners with cold, hard facts about themselves when they’re cornered into a survey, or recorded with a mobile tracking device. However, such measurements fail to capture the ambiguity underlying the measurement itself. What’s more, by obscuring complexity, this kind of easy categorization creates a false certainty that leads to strategic overreach.

Most business databases still categorize gender identity into only two categories: male and female. Transsexual Americans defy this easy division, however, with social genders that differ from their chromosomal gender markers. There have always been people who have been born intersex, but assigned one of the two traditionally-recognized genders. Now, increasing numbers of Americans identify themselves as gender fluid, reflecting an experience of gender identity that refuses to be placed permanently in any category.

Businesses that cannot work with such ambiguity are unable to practice true commerce. Commerce, after all, isn’t a matter of cold, hard numbers. It’s an intimate encounter that takes place at the crossroads of identity, where brands and consumers find themselves by finding each other’s embrace. It’s worth remembering that “commerce” is a word that refers to sex as well as to merely economic transactions.

The soul of commerce is found not in those who deliver enthusiastic elevator pitches for the latest app, but in those who feel a longing for lost connection. The writings of Fernando Pessoa suggest that the loss of connection hasn’t only harmed the customers that business claims to serve, but has impoverished business as well.

There is a temptation to measure consumers as singular sources of data, but to yield to that temptation is to descend into certain absurdity. Pessoa wrote, In its search of singular “true identity”, businesses are chasing shadows. The pursuit of hard facts where hard facts do not exist will lead businesses into the increasingly precise tracking of irrelevancies.

4. Keep It Real With Ritual

Photo by Jeremy Wong on Unsplash

All this talk of ambiguity and multiplicity will seem like too much for many Masters of Business Administration, who have been taught that they will be unable to manage anything that cannot be measured. They can take comfort, however, in the fact that ambiguity has always been a part of the human experience, and people have always had tools to deal with that ambiguity. From ancient times, societies have used rituals to translate the confusing analog quality of human nature into a manageable clarity.

Rituals embrace ambiguity and disruption, but contain and resolve it, so that social systems and the people who inhabit them can proceed in an orderly manner. They establish alternate threshold spaces within which alternative rules apply, giving people permission to perform acts of self-maintenance that would not be allowed in any other setting.

Pessoa urged his readers to pursue such rituals of self-renewal. He wrote in the Book of Disquiet, It is no coincidence that bathing is performed as a ritual act in cultures around the world. To enter into a ritual is to clean the psyche, stripping it of the costume of social identity performed for others, purifying it of conceptual grime, and preparing it to emerge back into society wearing a fresh disguise.

Photo of morning bath at the Apteshwar Mahadev Temple by @igorovsyannykov

Fascinated with self transformation, Fernando Pessoa sought rituals he could use to change between his heteronyms as we change suits of clothes. Ritual, after all, is the ancient technology of transition between identities. Rituals of graduation move us from childhood to adulthood. Rituals of marriage shift us from single to married status. Funeral rites mark the passage from life into death.

Pessoa was frustrated in his search for the rituals of his time, looking backwards to the ceremonial rhythms of his ancestors. He despaired, because these old rituals had been sapped of their power, and he could not understand the rituals of his own time. he wrote,

Fernando Pessoa instinctively sensed the power of the transcendent space of fluid identity created through ritual practice. he said in a moment of liminal awarenessPessoa’s engagement in the ritual process was without direction, however, because he could not grasp a cultural context with which to reorient himself. He was lost in the mist. His insomnia, shared by so many in modern life, was a symptom of a deeper disorder for which to this day we struggle to articulate a diagnosis.

In our time, we don’t find rituals in cathedrals or in secluded groves, but in the marketplace, in the form of commercial transactions. It’s the ritual act of purchase that gives us meaning, but too many consumers are like Pessoa, practicing commercial rituals that they don’t sufficiently understand. They reflexively sense what they’re supposed to be doing, but the commercial rituals they encounter are typically improvised, only partially constructed, as confusing as they are clarifying.

As studies of the rituals of Thaipusam demonstrate, it’s cultural context that makes sacrifice significant, transforming ordeals into opportunities. In our culture, the rituals that we practice in the marketplace are covered in a shroud of rationality that prevents us from perceiving their deeper significance. As a result, instead of transcendent meaning, the sacrifices we make in commercial rituals often bring us only frustration and pain.

Businesses that learn how to use the elements of ritual can relieve their customers of this suffering, foster enchanting emotional experiences, build genuine brand communities, and grow corporate culture that runs deeper than ping pong tables and Starbucks runs.

5. Honor the Mystical Foundation of Commerce

At the Foot of Hermes by Project 128

Once upon a time, business was sacred.

This isn’t a just-so story, but an historical fact. Economic trade as we know it was begun in ancient Greece under the auspices of the god Hermes. Hermes, going by the name Mercury in the Roman Empire, spread the practice across the Mediterranean and beyond.

It is often said that Mercury was the god of commerce, but it’s more accurate to say that commerce was an act of devotion to Mercury. Commerce, after all, is derived from the compound word com-Merx, meaning to be with Mercury.

To the Greeks and Romans, business wasn’t just business. Trade was a mystical act, a shapeshifting of value from one form to another. The coin was to them a talisman, a symbol of transformation, represented in the ability of metal to change shape, moving between solid and liquid form to be minted as a unit of worth. Mercury was not just the name of a god, of course, but was also quicksilver, the only metal that remains a liquid asset at room temperature.

You don’t have to accept the tenets of this ancient religious belief at face value to understand the power of its metaphor. To this day, business is built upon the transformation of time into money, of desire into action, with wealth shifting shape from one form to another through every transaction.

Fernando Pessoa was a devotee of a late-surviving aspect of the old hermetical beliefs. He studied alchemy, the mystical pursuit of the transformation of base elements into precious gold. Alchemy, in its literal form, gave rise to chemistry, but it was also a figurative practice in which the base nature of the practitioner’s character could be elevated to something more noble, untarnished and shining.

A person in business might object that things such as alchemy and ancient mythology have no place in commerce, which should be conducted rationally. In practice, however, even the most rational business cultures work with the hope that others will behave irrationally. Economic trade, when it is not automated, is enacted as a metaphor. When we let go of some value in the hope of something else, we aren’t just performing practical problem-solving behavior. We’re making a sacrificial statement about the distance between who we are and what we hope to become.

Under the heteronym Bernardo Soares, Pessoa worked on the Rua Dos Douradores — the Street of the Gilders. Gilding is the process of surrounding base metal with a thin layer of gold. Gilded objects aren’t transformed through any alchemical process. Their nature is merely concealed.

When we ignore the underlying transformational power of the transactions we seek in business, we become gilders rather than alchemists. We don’t build treasured brands so much as assemblages of gimmicks.

The vision of Fernando Pessoa leads us in another direction, toward a reflective and empathetic practice of business in which the simple, mundane objects and experiences that are our stock in trade are taken of tokens of a deeper pursuit.

A few weeks from now, I’ll be leading an unusual excursion of residents from the House of Beautiful Business into the streets of Lisbon. We’ll be following in the footsteps of Fernando Pessoa as we visit the places where he translated the business of despair into a poetry of mysterious longing. It’s an opportunity to, in a world of lean startups and sans serif fonts, get into the thick of what it means to live meaningfully in a world of commerce. Join us.

Using thick consultation & qualitative research to pursue a human vision of commerce, emotional motivation, symbolic analysis & ritual design