The Anti-Shackleton Manifesto

How Modern Leaders Win by Letting Things Die

In 1915, Ernest Shackleton made history by keeping every member of his Antarctic expedition alive. When his ship became trapped in Antarctic ice, he faced an impossible choice: preserve his vessel or save his crew. After months of trying to save both, he was forced to abandon his ship, leading his 28-man crew on a harrowing 720-mile journey across frozen seas in small lifeboats. Against all odds, he didn't lose a single man. The expedition failed its original mission but succeeded in something greater: perfect survival against nature's harshest conditions.

In 2020, Brian Chesky made history by deliberately reducing 25% of Airbnb. We celebrate Shackleton's perfect survival. We rewarded Chesky's strategic death with a $100 billion IPO.

In 2023, founders are told to "be like Shackleton" as tech companies reduce workforces. But this advice is misguided. He would have been a terrible startup CEO because of his refusal to let anything die.

Why Shackleton Would Fail Today

The appeal of the Shackleton story is clear. In crisis, we want to believe grit and unity can overcome anything. While his men survived by dragging a heavy lifeboat across ice, modern companies fail from this instinct. They refuse to abandon anything until the weight crushes them.

In the past decade, 52% of Fortune 500 companies vanished not due to inability to survive, but because they tried to survive everything. They followed the Shackleton playbook in an environment that demands strategic abandonment.

The Anti-Shackleton Playbook

Where Shackleton fought to preserve everything, Airbnb's Brian Chesky showed the modern alternative. In 2020, he did the unthinkable: systematically eliminating healthy parts of his business. Not because they were failing, but because they were good in a moment that demanded great. Eight months later, Airbnb was thriving at a $100 billion valuation.

This wasn't ruthless - it was responsible. While Shackleton's preservation ethic saved lives in Antarctica, in startups it often leads to larger casualties. The most beneficial decision is the earliest one, made while you have the resources and clarity to execute it well.

In 2023's tech winter, this principle separates companies that will emerge stronger from those that will preserve themselves to death. To understand why the Shackleton instinct fails in modern business, we need to examine the trap of perfect survival.

When Perfect Survival Kills

Shackleton's greatest triumph was preserving everything - his men, ships, and supplies. But in business, this instinct has resulted in some of history's failures. Consider Kodak, whose story reads like Shackleton's expedition in reverse:

In 1975, Kodak engineer Steve Sasson invented the first digital camera. Like Shackleton facing his first ice floe, Kodak faced a choice: adapt or preserve. They chose preservation. "That's cute," they said, "but don't tell anyone." They were protecting their film business, people, and processes - dragging their analog lifeboat across a rapidly digitalizing landscape.

Reed Hastings at Netflix was the anti-Shackleton. When faced with his own ice floe - the shift from DVDs to streaming - he didn't try to preserve everything. Instead, he ended Netflix's thriving DVD business years before he had to. Wall Street screamed. Customers revolted. The stock crashed.

Today, Netflix is worth $240 billion, and Kodak filed for bankruptcy.

The "Shackleton trap" - perfect preservation leading to death - repeats across industries:

• BlackBerry kept its keyboard until touchscreens made it irrelevant.

• Nokia preserved hardware excellence until software made it obsolete.

• Blockbuster preserved stores until streaming made them unnecessary.

Each company followed Shackleton's preservation instinct perfectly. Each died because of it. They achieved what he did - keeping everything alive - until that achievement destroyed them.

Not All Deaths Are Equal

Even leaders who reject Shackleton's "preserve everything" approach can fail in execution. Meta's 2022 metaverse pivot offers a masterclass in how not to eliminate things.

While TikTok was outperforming Instagram, Zuckerberg attempted a peculiar hybrid of Shackleton and anti-Shackleton. He tried to preserve Instagram's core business while building an escape route to a new digital continent. Like Shackleton attempting to drag his ship across the ice while building a new one, Meta burned $23 billion on Reality Labs while TikTok doubled its user base.

The anti-Shackleton approach would have been different: eliminating parts of Instagram - its feed-based structure, focus on polished content, advertising model - to compete with TikTok. Instead, Meta made the worst choice: preserving everything while betting on an escape that does not exist.

Under Satya Nadella, Microsoft shows the alternative. When faced with mobile's threat to Windows, he didn't try to preserve Windows' dominance or escape to a new reality. Instead, he abandoned Microsoft's "Windows first" philosophy, shifted resources to cloud, and made several significant changes. The result? Microsoft's value tripled while Meta's halved.

Shackleton's Choice: Design Death or Default Death

Shackleton faced a binary choice: abandon his ship or let the ice destroy it. Modern companies face the same choice, but most make a mistake: they pretend it doesn't exist.

In 2019, consider WebEx. Like Shackleton's ship trapped in ice, WebEx was trapped in enterprise software conventions. They had Shackleton's resources (their ship), loyal crew (enterprise relationships), and proven methods (their platform). But where Shackleton abandoned his ship, WebEx chose a different path. They preserved their existing business while Zoom - the anti-Shackleton - eliminated features, simplified interfaces, and moved away from conventions.

The result was predictable. WebEx's "survival" through preservation led to slower death, while Zoom's strategic abandonment led to dominance. This reveals a crucial truth: in business, unlike Antarctica, refusing to choose is a choice - usually the least favorable one.

The Price of Preservation

When Shackleton abandoned his ship, the delay nearly killed his crew. In business, the mathematics of delayed death are brutal. A 10% strategic cut delayed six months becomes a 10% forced cut - it spreads uncontrollably:

• The cut doubles (20% instead of 10%)

• Resources are wasted preserving doomed initiatives

• Competitors advance while you do not

• The market labels you as reactive, not strategic

• Your best talent leaves, seeing the ice closing in

This is why modern anti-Shackletons like Airbnb's Chesky cut early and deep. They understand that in startups, unlike Antarctica, delayed abandonment isn't prudent - it's fatal.

The Anti-Shackleton Protocol: Stripe's Systematic Approach to Death

If Shackleton's approach was preserving everything at all costs, what does the opposite look like? In 2022, Stripe showed us an unprecedented systematic protocol for strategic death.

Where Shackleton had to make quick decisions, Stripe created a deliberate, three-phase approach to choosing what dies:

Phase 1: Death Audit (Weeks 1-3)Unlike Shackleton's "save everything" mandate, Stripe mapped everything against three questions:

• Essential for survival?

• Worth its resource cost?

• Speeding up or slowing down?

Phase 2: Death Design (Weeks 4-6) After identifying death candidates, Stripe created a precise hierarchy: what dies first, next, and how to preserve critical knowledge from each death.

Phase 3: Execution (Weeks 7-12) The final phase followed one key principle: Products died before processes, processes before people. Speed was more important than perfection.

Result? While other companies debated what to preserve, Stripe emerged stronger, leaner, and more focused.

The Anti-Shackleton Diagnostic

Shackleton had a simple rule for preservation: everything essential to survival. But in startups, this instinct leads to disaster. We need a different diagnostic to identify what should be eliminated before circumstances force our hand.

The Anti-Shackleton Diagnostic flips Shackleton's preservation mindset. It asks four brutal questions that challenge our survival instincts instead of asking, "What must we save?:

The Anti-Shackleton asks four questions:

1. "Would we suffer if this died tomorrow?"

2. "Are we keeping this alive out of pride or necessity?"

3. "Is this consuming resources disproportionate to its impact?"

4. "Would we build this if starting today?"

Any "no" answer flags something for death. Identifying what to eliminate is only the beginning. The real challenge? Actually taking action.

The Final Test: Execution

Even Shackleton hesitated before abandoning his ship. That moment of hesitation - the gap between knowing what must die and actually killing it - nearly doomed his mission. Today's companies face the same challenge, but with higher stakes.

This execution gap kills more companies than poor strategy. BlackBerry diagnosed correctly but couldn't eliminate their keyboard. Blockbuster saw streaming coming but couldn't abandon stores. Nokia knew Symbian was dead but kept it alive. Each hesitated, hoping for a perfect moment that never came.

To bridge this gap, we need to reverse Shackleton's principles:

1. Speed Over Perfection

   Shackleton waited for perfect conditions. Airbnb didn't. In March 2020, they made swift, imperfect cuts while others planned perfect ones. The result? Airbnb recovered. The planners failed.

2. Sequence Over Size

   Shackleton tried saving everything equally. Modern leaders can't. The sequence matters more than size:

   • First, kill products (they don't have families)

   • Next, kill processes (they can be rebuilt)

   • Kill jobs last (if necessary)

3. Clarity Over Comfort

   Shackleton's crew needed hope more than truth. Today's teams need the opposite. They need to know:

   • What's dying (and why)

   • What's safe (for now) • What criteria will drive future deaths

In startups, false comfort kills more surely than hard truth.

The New Antarctic

History remembers Shackleton for one metric: 28 men in, 28 men out. But today's business landscape is a different kind of Antarctic:

• Market share declines rapidly

• Competitors advance steadily

• Resources deplete quickly

• Team morale fluctuates

• Innovation demands increase rapidly

In this new Antarctic, perfect preservation isn't just impossible - it's fatal.

The Ultimate Irony

Shackleton's story holds one final lesson: his obsession with preserving everything nearly killed his entire crew. Only by abandoning his ship - his one deliberate death - did he save his crew.

Today's leaders face this choice daily. Where Shackleton had to learn to kill one big thing, we must master continuous, strategic elimination. The winners won't preserve everything, but perfect the art of choosing what to eliminate - repeatedly.

The Anti-Shackleton's Creed

"Men wanted for hazardous journey. Safe return not guaranteed.”

"Leaders wanted for continuous transformation. Safe preservation is impossible. Must be willing to eliminate what others would save, abandon what others would preserve, and find growth through deliberate endings."

In 2023's uncertain waters, that's the leader we need. Not Shackleton with his preservation instinct, but the Anti-Shackleton with their strategic sacrifice. Because in startups, unlike Antarctica, perfect survival is the surest path to death.

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