Surface Geography and Underground Geology of Leadership Land

Surface Geography of Leadership Land

Map not to scale. Environmental hazards are subject to geographical dislocation. Ask your doctor if this map is right for you. Side effects may include disorientation, vertigo, agoraphobia, sporadic bursts of ambition, and halitosis.
Hand-drawn map! Why use Adobe Creative Suite when you can smear your thoughts all over with Microsoft Paint?

Welcome to Leadership Land: a dangerous and exotic place where the risks might be worth the rewards. Whether you’re a Harvard Business School graduate with your eyes set on the fiery peak of Executive Mountain, or a migrant manager with humbler, amorphous ambitions, let this map be your guide! Some of the major features of Leadership Land’s surface include:

Boss Forest

Where most leaders start out after crossing the Interview Mountains. Those who seek mentors and external assistance can find their way out with relative ease. Others are stuck for much longer, mired in day-to-day tasks and struggling to see the forest through the trees.

Career Swamp

The unexpected and (usually) unplanned destination of many careers. Once trapped in the stagnant waters of the Career Swamp, it becomes exceedingly difficult to bootstrap oneself out. Those who perish in the Swamp are sucked downward into the Silent Graveyard beneath Leadership Land.

Desert of Good Intentions

Many travelers end up here by blindly following advice from leadership “experts” (often conveyed via TED talks, self-help books, or Harvard Business Review articles). By applying too much of a good thing, employing a good technique in a bad place, or using the right method at the wrong time, these leaders are swallowed by the unintended consequences lurking beneath the Desert’s shifting sands.

Executive Mountain

This active volcano towers over Leadership Land, serving as a beacon for ambitious leaders. Those who rise to the challenge (often HBS graduates) must climb its treacherous slopes to claim one of the C-suites near the peak. Once there, they can enjoy a 30,000 foot view of Leadership Land from their corner offices…but they’re never safe. The summit of Executive Mountain is known for its violent eruptions, and high-level leaders are the most endangered by the lava flows.

Interview Mountains

This mountain range rings the periphery of Leadership Land, serving as a formidable barrier to entry against those unworthy of directing other human beings (though there’s some leakage through Nepotism Pass and the Crony Caves). Elaborate mating rituals take place in these mountains, with aspiring leaders attempting to gain entry into Leadership Land by impressing the gatekeepers. Given the incentives for interview candidates to embellish, and the gatekeepers’ roles in inferring capability with very little information, the Fog of Uncertainty is extraordinarily dense in the Interview Mountains1.

Institute of Conventional Wisdom

The Institute’s campus radiates dignity and prestige. Academics and New York Times bestselling authors, dressed conservatively in dark suits, sip Earl Grey tea on the meticulously-groomed quadrangle. The Institute’s buildings are impeccably proportioned with straight lines and Euclidean shapes, their exteriors gleaming with polished stone and their interiors paneled in rich mahogany. The west wing of the Institute comprises the Tower of Corporate Astrology, which soars into the skies above Leadership Land like a middle finger in defiance of the Fog of Uncertainty2.

Everything about the Institute suggests intelligent design, domestication of the unknown, and the triumph of human foresight over the vicissitudes of fate. The Institute’s “best practices” (generally considered managerial canon) are carefully studied by leaders of all stripes, from first-time managers in the Boss Forest to visionaries atop Executive Mountain.

To an academic know-it-all, the world is a brightly-lit place where the darkness of un-knowledge is unworthy of attention. In the real world, each piece of un-knowledge is a secret; widely-accepted knowledge is rarely worth pursuing.
To trick the casual observer into believing that the Institute of Conventional Wisdom is the keeper of esoteric secrets, its coat of arms bears the Latin inscription Sola lux et veritas (“Only light and truth”). True to this motto, the Institute believes that anything not illuminated by its brilliance is unworthy of consideration.

Unfortunately, the rest of Leadership Land watches the Institute so closely that it has become a victim of its own success. The Institute was originally built from Cerebrium (crystalized secrets) mined in the Secret Grottos. However, the very act of exposing and widely disseminating yesterday’s secrets converts them irreversibly into tomorrow’s conventional wisdom. The Cerebrium transported from the subterranean depths of Leadership Land quickly loses its ability to help leaders “get ahead” or maintain a competitive advantage.

The Institute of Conventional Wisdom seems oblivious (or willfully ignorant) of the fact that converting secrets into conventional wisdom often decreases the potency of the knowledge3. The Institute continues to pride itself on its inert Cerebrium, and this façade of erudition continues to hoodwink leaders into believing that the Institute is infallible.

Fog of Uncertainty

The Fog of Uncertainty is ambiguity incarnate. It is composed of aerosolized vagueries suspended in a cloud of vaporous doubts. The Fog is ubiquitous in Leadership Land because:

  • Leaders must make decisions with incomplete information. Sometimes, we don’t even know whether we’re missing crucial information.

  • The information we do have is often outdated or low-quality. It’s difficult to check if our information is half-right, totally wrong, or 100% right but conditional on other factors.

  • Even if we had 100% of the relevant facts, and the relevant facts were 100% true, all decisions are subject to some randomness, variability, and luck. Even if it worked for 1,000 days, it could fail on day 1,001. The more unexpected the failure, the more unpleasant the surprise!

The Fog of Uncertainty is what makes Leadership Land so difficult to navigate. You’ve probably never seen a five-year plan that includes “perish in the Desert of Good Intentions.” No one has ever put “go skinny-dipping in the Career Swamp” on their bucket lists.

Middle Management Foothills

Clustered around the base of Executive Mountain, the Middle Management Foothills are home to medieval fiefdoms ruled by a feudal lord. These middle managers could be up-and-coming leaders destined for the C-suite…or they could have topped out professionally, and their domain is slowly crumbling into the Career Swamp.

Plague Plateau

“I was hiding under your porch because I love you. Can I stay?”
This is technically a tepui, but it doesn’t alliterate as well as “Plague Plateau.” CC-BY-SA photo courtesy of Heribert Dezeo

Satellite offices, separated by physical barriers, tend to develop distinct cultures and processes over time. Organizational units, siloed by institutional barriers, will diverge from one another without central control. The Plague Plateau, separated from the rest of Leadership Land by vertical cliffs of stone, has evolved into a quarantine zone known for breeding a diverse array of organizational diseases.

Conveniently shaped like a skull and crossbones, the Plague Plateau is the origin of epidemics such as pseudo-productivitis and bureaucratic bloat. The Plague Plateau is responsible for many Lollapalooza Effects, both mild and wild, that catch the rest of Leadership Land by surprise.

Straits of Conflicting Interests

The Straits comprise a tidal region where self-interests ebb and flow in a cyclical struggle against the greater good. The region is home to:

  • Rocky shoals and issues

  • Narrow channels and minds

  • Turbulent waters and emotions

All of which make the Straits of Conflicting Interests extraordinarily difficult to navigate – a challenge compounded by the Fog of Uncertainty.

Temple of Trust

Trust is sacred in Leadership Land. To build trust, leaders must construct a temple with bricks of integrity, held together by the mortar of vulnerability, all atop a rock-solid foundation of credibility. Inside the Temple is an altar of psychological safety, which the leader must protect from the taint of mistrust.

Building a temple and maintaining the purity of the altar is hard work. Most managers take the easier, ineffective route of throwing some icebreakers, potlucks, and other “teambuilding activities” at their teams a few times a year, then praying for a miracle.

Subterranean Geology of Leadership Land

Cross-section not to scale. Subterranean features are subject to geology puns. Ask your volcanologist if this map is left for you (yes). Side effects may include claustrophobia, pyrophobia, thalassophobia, phasmophobia, spelunkephobia, phobophobia, and panphobia.
Computer-drawn map! With Adobe Creative Suite, you can smear your thoughts all over while glaring condescendingly at all the peasants using Microsoft Paint.

The surface world of Leadership Land is brightly lit; you’ll be able to find anything from that sun-kissed realm with a quick Google search4. The dimly-lit underground of Leadership Land is where you’ll find the stuff that few people think about, and fewer people talk about. Down here, you’ll find unconventional thinking, controversial views, and subversive methods (for offense against competitors, defense against encroachment, or undermining internal saboteurs)5.

Ancient Repositories

You won’t find any original thinking on Adventures in Leadership Land. We’re not smart or clever enough to generate new ideas. We only have the creativity and intellectual horsepower to plagiarize borrow ideas from superior thinkers who preceded us, connect the dots, and resell their ideas in modern packaging6. Sometimes, a very-old idea created by a very-dead guy has aged like fine wine, rather than like milk. Instead of re-packaging their intellectual vintage, we’ll simply pull it out of the Ancient Repositories to share with you.

Contrarian Caves

The Contrarian Caves are antithetical to the Institute of Conventional Wisdom. Unlike the Institute’s centralized control over what’s “right” versus “wrong,” the Contrarian Caves form a dogma-free, decentralized network. The walls of the Contrarian Caves are rough and jagged, in stark contrast to the Institute’s straight lines and Euclidean architecture. The motto of the Contrarian Caves, written in English vernacular, stands in direct opposition to the Institute’s pretentious Latin motto:

Follow conventional wisdom, get mediocre results.

These Caves are home to the mavericks, iconoclasts, and exiles who march to the beat of their own drums. Many of these contrarians are more concerned about results than appearances7. They can:

  • be right while appearing wrong

  • look poor while being rich

  • ask stupid questions while decreasing their own stupidity

Despite the value of visiting the Contrarian Caves, few leaders do. The Caves are filthy, counterintuitive, and often incomprehensible. There’s zero prestige in elevating messy practice (“what works”) above elegant, smart-sounding theory (“what should work”). Independent thought is a lonely venture; many leaders are uncomfortable toiling away in a dark, grimy cave with only their ideas for company. Most difficult of all: leaders must strive to be contrarian and correct. Being contrarian and wrong is often worse than simply following the Institute’s conventional wisdom. For these reasons, many “leaders” prefer to be led (as authoritative followers) than to actually lead.

You’re probably wondering: why would contrarians continue lurking underground if the Caves are dirty, lonely, and unpopular?

It’s because the Contrarian Caves are adjacent to the Secret Grottos, which contain rich veins of Cerebrium (crystalized secrets). The discovery of a secret is the only vindication a contrarian will receive for an unpopular belief. Leaders who follow conventional wisdom will get conventional results, but contrarians who toil away in the Cerebrium mines can use their secrets to achieve superior results. In this regard, the obscurity of the Contrarian Caves is a blessing, not a curse – it allows practitioners to exploit Cerebrium without divulging their secrets.

Our most popular essay provides guidelines on when to follow conventional wisdom, and when to think like a contrarian.

Fiery Hells of Competition

The Fiery Hells are a network of magma chambers located deep below Executive Mountain. The friction of competition generates enough heat to melt rock into magma. Competitive pressures squeeze the Fiery Hells, forcing magma all the way up to the summit of the volcano. The magma chambers scorch all that they touch – some leaders will perish in the searing heat; others will re-forge themselves in the fires of adversity and emerge tougher than before.

The most ambitious leaders eagerly throw themselves into the fires of adversity, like some religious rite of passage, to prove that they “have what it takes.” Even those with more modest goals still believe that competition is an ideal state (think of all the people aiming to be “more competitive”). Leaders from the Contrarian Caves beg to differ, believing that competition is a destructive force best avoided whenever possible.

Liar’s Lair

Leadership is full of self-deceptions, mandatory insincerities, polite fictions, and cherry-picking. We sometimes tell well-intentioned “white” lies, and other times we tell strategic falsehoods to throw competitors off our trail. Other people are doing the same things, opening up some interesting game-theory mechanics. We behave differently when we know they’re lying, which causes them to behave differently when they know that we know they’re lying.

But we don’t visit the seedy tavern in Liar’s Lair merely to people-watch. We’re also interested in the arms race of deceit, how a lie can indicate the presence of a truth hidden nearby, and the strategic value of authenticity when everyone else is lying.

Secret Grottos

The gloomy, grimy Grottos are home to the Cerebrium mines. Extracting Cerebrium is a miserable process, requiring miners to dig and pry at the fringes of the Unknown Abyss while fumbling and stumbling around in the dark. But the miners willing to toil away in obscurity are rewarded with a valuable treasure: a glint of enlightenment in solid form.

"I am inevitable." | "Hi, inevitable. I'm Iron Dad."
Thanos A miner admiring the Tesseract a chunk of freshly-mined Cerebrium.

Each piece of Cerebrium is a crystallized secret. It could be arcane knowledge or an unconventional technique that empowers the owner to seize a greater share of the pie (competition and scarcity), to grow the overall size of the pie (innovation and abundance), or both. Cerebrium is a precious resource for upwardly-mobile leaders, inventors, and scientists.

Here’s a chunk of Cerebrium for you, free of charge. But try not to spread it around too widely…

Cerebrium has a curious property: the more people behold its light, the faster it loses its glow. Eventually, it becomes an inert lump of crystal. By definition, secrets are not widely known; a widely-known secret is just common knowledge. Transport Cerebrium from the subterranean bowels up to the densely-populated, high-traffic surface of Leadership Land, and you will deactivate the very thing that made Cerebrium valuable in the first place.

The Institute of Conventional Wisdom was originally built from glowing Cerebrium. After all, every bit of “common knowledge” we take for granted today was a secret to our ancestors at some point8. But those secrets have been converted into conventional wisdom, and the crystals have grown dull. The Cerebrium’s potency has been extinguished by the gaze of all the people who visited the Institute.

Silent Graveyard

Beneath Leadership Land is a vast cemetery of leaders whose names and deeds we’ll never hear about. The Silent Graveyard is haunted by the ghosts of:

  • People with amazing potential who were born in the wrong place at the wrong time (e.g. a mathematical genius born into the toilet-scrubber caste during a dark age when studying math was considered heresy).

  • Intelligent, hard-working, and daring entrepreneurs whose risk-taking landed them in the Silent Graveyard rather than onto the cover of Forbes magazine.

  • Visionary leaders who successfully prevented pandemics, world wars, and zombie apocalypses, but who died in obscurity because the disasters that never happened aren’t “noteworthy.”

Contrast that with the surface of Leadership Land, where every schoolchild is indoctrinated with the biographies of famous leaders, inventors, and scientists who happened to be born in the right place at the right time. Every business school has a shrine to the risk-taking entrepreneurs who happened to “make it.” Historians normalize our hero worship by writing books about the leaders who saved us from extinction, but never about the ones who prevented existential crises from ever occurring.

The bigger the Silent Graveyard → the more famous the survivors → the worse our survivorship bias → the more distorted our definition of “success.”

Only by studying the phantoms of survivorship bias can we rectify our distorted perception of what “success” really means. The problem is…the Silent Graveyard is very, very silent. It doesn’t call for our attention, so we have to deliberately schedule a visit. Anyone up for some ghostbusting?

Taboo Tunnels

The Taboo Tunnels are created by social inhibitors. The Tunnels contain all of the things left unsaid. Each tunnel is a physical manifestation of the void created by a breakdown in communication. Each entrance to a Taboo Tunnel starts with a euphemism, and the rest of the tunnel is drilled through solid rock by the 800-pound gorillelephant in the room, ridden by an emperor with no clothes.

The Taboo Tunnels are the primary routes for traveling between the surface and the underground of Leadership Land. Even though the subterranean map only shows the two biggest Tunnels connecting Liar’s Lair to the Desert of Good Intentions and the Straits of Conflicting Interests, there are many other Taboo Tunnels crisscrossing the depths of Leadership Land.

Unknown Abyss

The Unknown Abyss is cloaked in the perfect darkness of anti-knowledge. Don’t let appearances fool you; the anti-knowledge may look uniformly dark, but it comes in very different flavors:

  1. Secrets: things we don’t know…yet. The Unknown Abyss contains glowing veins of Cerebrium waiting to be discovered. Miners in the Secret Grottos are constantly encroaching on this part of the Abyss, transmuting anti-knowledge into knowledge.

  2. Mysteries: things that definitely exist, but can’t be accurately measured (e.g. support for a coup d'état) or predicted (e.g. the next earthquake or market crash). Mysteries correspond to the “known unknowns” in Rumsfeldese, or the “gray swans” in Taleb-speak.

  3. Inconceivabilia: things that are impossible to know9. We’d provide an example, but then the example would belong to the “Mysteries” category rather than this one. Inconceivabilia are analogous to the “unknown unknowns” in Rumsfeldese, or the “black swans” made famous by Nassim Nicholas Taleb.

The Unknown Abyss is responsible for tremendous destruction and misery. The unseen, the unheard, and the unknown can hurt you a lot more than what you do know and are prepared for. On the other hand, the Unknown Abyss is also the wellspring of discovery, pleasant surprises, and serendipity. As Nietzsche once wrote (paraphrased):

What’s unintelligible to me isn’t necessarily unintelligent.

We live by the words “hope for the best, prepare for the worst, capitalize on what follows.” Embrace positive unknowns and welcome happy accidents. Protect against negative unknowns, both Mysteries and Inconceivabilia. You will never be fully prepared when a massive black swan emerges from the Unknown Abyss, but you will be less unprepared than everyone else – allowing you to capitalize on what follows.

Let’s explore Leadership Land together – from its brightly-lit terrains to the shadowy depths where the greatest dangers and most valuable secrets can be found.

Share Adventures in Leadership Land


Just like the Mountains of Shadow surrounding the land of Mordor.

One blog to rule them all, one blog to find them;
One blog to bring them all, and in the Fog of Uncertainty bind them.
In the realm of Leadership Land where everyone lies.


The Institute of Conventional Wisdom is sealed against the Fog of Uncertainty. It’s one of the few places on Leadership Land’s surface where the Fog does not penetrate.


This is only applies in competitive environments (e.g. zero-sum games) and some dynamic systems. This is not true in mathematics, art, and underwater basket-weaving (where discoveries and new techniques are rising tides that lift all boats).


Sure, you could read about the same things on straight-laced publications like the Harvard Business Review. But it won’t contain our colorful commentary and misanthropic snark.


“Subversive” does not mean “illegal.” This blog is about avoiding failure; habitually breaking laws tends to buy you a one-way trip to the Career Swamp.


Newton’s quote:

If I have seen further [than others], it is by standing on the shoulders of giants

is too grandiloquent for us. We’re not even tall enough to climb onto the shoulders of giants, so we resorted to breaking into their houses and stealing their stuff.


Some denizens of the Contrarian Caves are anti-establishmentarians who take the contrarian view solely to raise a middle finger in defiance of the mainstream. We’re not interested in their ideals or politics; we’re only interested in results. See our guidelines on when to follow conventional wisdom and when to think contrarian.


A lot of things we consider obvious in hindsight used to be secrets. Consider that the first U.S. patent for a suitcase with wheels came after we landed a man on the moon (the wheeled luggage was invented before that, but the patent came almost two decades later). Or consider that splinter-free toilet paper was a novelty back in the 1930s. There are people alive today who suffered from sphincter splinters!


Impossible to know until they happen. After they occur, we look through the lens of hindsight and honestly believe that the occurrence was more predictable than it really was. Retrospective explainability is a hallmark of Taleb’s black swan theory.