The Curse of the Spanish Armada: When Scale Becomes Self-Sabotage

In 1588, King Philip II of Spain launched a naval campaign that should have been the climax of Catholic Europe's struggle against Protestant England. The Spanish Armada, 130 ships strong and carrying more than 30,000 men, was to sail through the English Channel, rendezvous with Spanish ground forces in the Netherlands under the Duke of Parma, and deliver a crushing blow to Queen Elizabeth I's rule. It was a plan that relied on the immutable power of overwhelming force, blessed by divine purpose and sanctioned by imperial ambition.

But the largest fleet ever assembled in Europe was routed.

The defeat of the Armada has often been ascribed to celestial winds and English luck. But this lets Philip off too easily. The Armada failed - not in spite of its size, but because of it.

The campaign relied on absolute obedience and sequential execution: the Armada would arrive in the Channel, hold position, and wait for the Duke of Parma’s forces to sail out. But Parma didn’t control the seas. He had no deep-water port for his men to embark safely. Communication between the fleet and the ground forces was practically nonexistent. Messages took days to travel over land and were further delayed by weather and enemy patrols. The two halves of the plan—naval and land—never connected.

While the Spanish lumbered in their rigid formation, the English navy attacked with faster, more maneuverable ships. Commanders like Francis Drake and Charles Howard exploited their mobility, striking the flanks and retreating before Spain could react. The English avoided boarding combat, which the Spanish preferred, and instead pounded the Armada from a distance. Fireships scattered the Spanish line at Calais. Chaos followed. The plan collapsed.

After the failed rendezvous, the Armada had no choice but to sail north around Scotland and Ireland to return home. But storms battered the weakened fleet. Dozens of ships were wrecked on unfamiliar coasts. Thousands of sailors died. Of the 130 ships that left Spain, only about half made it back.

The Spanish Armada wasn’t defeated by a superior force. It was defeated by poor coordination, inflexible design, and an inability to adapt. Its sheer size became a liability. The bigger it was, the slower it turned, the more fragile it became.

The Illusion of Bulk Advantage

Scale confers certain powers: network effects, economies of production, capital leverage. But it also creates cognitive distortions. Leaders of scaled institutions misinterpret their size as a moat. They think risk diminishes with girth. They presume their options grow with reach. They believe the future must route through them.

But operational size does not equal - or guarantee - any form of strategic clarity. The bigger the system, the more likely it is to misread local signals. This is a structural outcome of hierarchy and abstraction. Every level between decision-maker and reality adds latency and distortion. Like the delayed relay of wind conditions through the Spanish command chain, crucial information arrives too slowly to matter.

Philip II governed from a palace hundreds of miles from the coast, issuing orders through parchment and proxy. His empire stretched across continents, but his command relied on a brittle belief in control. Modern executives do the same thing with dashboards, org charts, and quarterly earnings calls, believing they’re in the thick of it because they monitor a handful of Slack channels. But the problem is timeless: the thicker the insulation between leader and edge, the less responsive the institution becomes to change.

WeWork, Boeing, and the Misapplication of Scale

WeWork raised billions to build a global network of coworking spaces. What began as a real estate arbitrage play morphed into a kind of metaphysical startup: a company selling community, vision, and cultural transformation at industrial scale. At its peak, WeWork leased more office space in Manhattan than any other company. It saw itself as inevitable.

But inevitability is a myth. The company mistook momentum for product-market fit and valuation for validation. It scaled its brand faster than it validated its economics. And when friction emerged—high burn rates, low occupancy, erratic leadership—the whole edifice began to wobble. The scale that once seemed impressive now looked like a liability. The very size of its commitments made adaptation impossible.

Boeing tells a parallel story. For decades, it stood as an icon of American industrial capability. Then came the 737 MAX. Under pressure to compete with Airbus and protect its market share, Boeing tried to do something fast: retrofit an old model rather than build anew. But the complexity of its internal systems—a legacy of mergers, offshoring, and management abstraction—meant that key decisions were siloed and safety warnings went unheard.

The crashes - technical failures - were systemic consequences of a scaled institution prioritizing continuity over scrutiny. The tragedy was not only in the deaths, but in the stubborn belief that a company of Boeing's size couldn't possibly get something so fundamental so catastrophically wrong.

Institutions That Get Lighter

Scale can still be an advantage - when it's accompanied by internal plasticity. The institutions that endure tend to build an almost shape-shifting capacity. They become modular, decentralized, layered. They learn how to make parts of themselves small again.

Modularity is why open-source software survives corporate implosion. No one owns it. Its parts can be forked, reassembled, adapted. It resists bloat because anyone can rebuild it from scratch.

Contrast this with the fate of sprawling governments - or even legacy newsrooms. When an institution becomes too entangled with its own infrastructure, even minor course corrections feel like amputations. Feedback loops slow down. Internal debates become more about policy than truth. And eventually, something nimbler eats their lunch. And then it eats them.

The Drift Toward Inevitability

There is a specific kind of ego that scale induces: the belief that history flows in your direction. The Spanish Armada Error is a fatalistic assumption that your sheer mass makes you the protagonist of history. The British should have folded. The weather should have cooperated. Competitors should concede, etc.

When WeWork styled itself as a movement rather than a business, it was a way to preempt criticism. Movements don’t require profit. They require belief. Boeing, too, leaned on the mythology of national prestige; IE, you don’t audit the flag.

But history doesn't care about your feelings. The waves will knock you over regardless of how noble your intentions are. And when your structure is too heavy to pivot, the fall is irreversible.

Small Is Not Always Beautiful

Small won’t always win. Small can be fragile. Small lacks resources. Nimbleness is not the same as strategy. A fleet of rowboats can’t always beat a battleship. But when the winds turn, rowboats don’t capsize from their own gravity.

The lesson isn’t to avoid scale; it’s to fear ossification. To treat every gain in size as a risk to feedback, speed, and humility, to design institutions that can reconfigure themselves under pressure. Institutions that can say, without ego, "This approach no longer works."

History is full of great ships that never made it to shore. Institutions that took their size as evidence of destiny. Strategies that worked until the world changed faster than they could turn.

Every organization that wants to survive the future should study the wreckage of the Armada. Not for the romance of empire or the spectacle of collapse (as much as those ideas appeal to my history-obsessed mind.)

For the structural warning it offers:

You can’t be too big to fail. But you can be too big to win.