Shackleton’s Endurance and Lessons in Adapting Your Strategy

On October 26, 1914, Ernest Shackleton, captain of the Endurance, set sail with a crew of twenty-seven men comprising the Imperial Trans-Antarctic Expedition. Their goal was to complete the first land crossing of the Antarctic. With an expedition of this difficulty, there was no shortage of planning or coordinating involved.

Shackleton’s final itinerary planned to take the Endurance into the Weddell Sea before disembarking near Vahsel Bay with a team of six men and seventy dogs to sledge across the Antarctic. At the same time, a second ship directly across the continent would sail into the Ross Sea, setting down provisions along the intended route for Shackleton and crew. This would keep the men supplied until they reached their final destination at the McMurdo Sound base. 

Ten days after setting sail from Buenos Aires, the Endurance reached South Georgia and received disheartening news at the whaling station. The conditions in the Weddell Sea were the worst in recent memory. As the Endurance continued south towards the Weddell Sea, they learned this first hand. 

In an open ocean the Endurance covered close to 200 miles a day. But facing polar pack ice they were slowed to a crawl and by December covered less than thirty miles a day. 

As they came within 200 miles of Vahsel Bay, fierce winds struck and they were forced to shelter the Endurance next to a large iceberg. After six days, on January 24, 1915, the winds began to subside but the Endurance was frozen solid in pack ice as far as the eye could see. 

The crew did their best to free the ship, chipping away at ice with chisels and saws. But after a month, the ship was still trapped. As the days grew shorter, Shackleton knew there was no immediate way out and no way to communicate with the outside world. 

Shackleton’s neatly made plans to cross the Antarctic came to an abrupt halt. It was now about survival and the preservation of his crew, which demanded an entirely new set of strategies. He gave the order to prepare for winter aboard the Endurance.

On the open sea, each man had their assignment. There was work to be done and they remained in good spirits. But with the ship out of commission, they faced a lull. And Shackleton feared demoralization more than the threat of ice or sub-zero temperatures. 

In an effort to keep the crew engaged and morale high, Shackleton directed the construction of “dogloos” on the ice to protect the dogs. He sent others hunting to secure a supply of meat for the winter. And he created a series of social occasions with grog on Saturday nights, music on Sunday nights, and dog-sledding races. The men remained in surprisingly strong spirits through the depths of winter. 

But when spring arrived, the Endurance showed no signs of breaking loose. Quite the opposite. After being trapped in pack ice for nine months, the Endurance was being slowly crushed by the Weddell Sea. On October 27, 1915, Shackleton gave the order to abandon ship.

While sheltered aboard the Endurance, they had room to store equipment for every imaginable scenario. But Shackleton recognized they were in a new territory of survival which would require sacrificing preparedness for speed. There was no room left for luxuries.

Shackleton urged the crew to leave behind anything that wasn’t absolutely essential for survival. To emphasize the seriousness of his request, he tore a page from the Book of Job, placed his Bible in the snow, and set off without looking back. 

Shackleton and the crew huddled to set up camp on a large nearby ice floe. They hoped the drift would carry them towards the safety of Paulet Island, 250 miles away. Despite the dire circumstances, the men were relieved to have a plan. The indecision and speculation aboard the Endurance was over. Shackleton knew not to let ambiguity linger for too long. 

Even as storms carried the floe in unexpected directions, Shackleton operated with conviction. Whether in demanding patience during the drift or taking deliberate action to relocate camp and board the lifeboats during a last-ditch effort to reach land. 

As conditions changed, Shackleton’s strategies would shift. But he remained purposeful in his every move. The crew held a deep respect and admiration for this. It’s what held them together during their bleakest moments. 

It took everything he had, but nearly two years after setting sail aboard the Endurance, Shackleton reached the shore of South Georgia Island with five of his men in the last remaining lifeboat. The rest of the crew remained on Elephant Island where they were rescued three months later. 

Shifting Strategies

Shackleton could have relied on the same strategies he had up until the Endurance was trapped in ice, but that would have meant certain defeat. Instead, he avoided disaster through his ability to adapt and rethink his strategy as the situation required. Nothing could have prepared him for the circumstances he faced. But he willed his crew to survival at every turn. 

When Shackleton gave the order to winter aboard the ship, he shifted his strategy from one of operations and efficiency, to survival and engagement. With polar nights and a perpetual darkness bearing down on them, he knew the real enemy was a sense of restlessness and complacency among the crew.

Nine months later when they abandoned the ship, Shackleton had to pivot again, favoring speed over preparedness. It was the opposite of his strategy while originally planning the expedition or aboard the ship, but he knew time was of the essence. Every spare second wasted hauling around non-essential equipment could mean the difference between life and death. 

Strategies are frameworks to help you to think ahead and take thoughtful action. But strategies won’t provide a checklist of prescribed actions for your every move in life. As Shackleton knew well, no matter how strategic you are, there’s no replacement for true resourcefulness. And this is where people get lost. The map is not the territory. 

It’s easy to get locked into a rigid thought process with a single strategy if you stick to the map without ever looking up. But when you stop reaching for absolutes, you’re able to embrace the motion inherent to life. Everything is fluid.

Shackleton embodied this in a survival scenario. But the same concept holds true even when you’re not fighting for your life while floating on a sheet of ice in the Antarctic. At a certain point, the strategy that might have worked for you up until this point in time will falter. Resourcefulness matters. Allow yourself to adapt.

This article is an excerpt from my recent e-book, 7 Strategies to Navigate the Noise. It’s all about sharpening your strategic mind, taking thoughtful action, and living on your own terms. Grab your free copy here.

For more details on the story of Ernest Shackleton and the Endurance, check out Alfred’s Lansing’s book of the same name.

The 5 Best Books to Sharpen Your Strategic Mind

Ever wonder if you’re focused on the right things? This fear defined my first five years out of college. I was mainly reacting to the things happening around me, bouncing from one distraction to the next. I tried to be purposeful but I had no sense of direction and failed to grasp the nuance of the long game. In other words, I failed to recognize the importance of strategy. 

At their core, strategies are the frameworks you stack to help advance your principles, move you closer to your goals, and realize your aspirations. Strategies sit above tactics, but below guiding principles. They pave the way forward and help create momentum.

A strong strategy helps to direct your focus and anticipate the obstacles or adversaries standing in the way. This requires long-term thinking – an ability so see multiple moves ahead and an understanding of the interconnected whole. But it’s also about knowing what you’re working towards and what’s within your control. 

This story will be familiar to those who have read my new ebook, 7 Strategies to Navigate the Noise. It’s all about connecting your guiding principles with your day-to-day. Life gets easier when you develop a stronger sense of strategy and are able to take thoughtful action. 

Over the past ten years, I’ve faced this question day in and day out, pouring over hundreds of books in an attempt to figure it out. In 7 Strategies to Navigate the Noise, I recommend twenty-two different books to improve your strategic mind. I’ve narrowed that list to the five most influential books on strategy to get you started.

Each book offers something of its own and was a major influence in helping me develop a stronger sense of strategy and self-sufficiency. If you’re struggling to determine whether or not you’re focused on the right things or need help sharpening your strategic mind, these books should provide a solid starting place.

1) The Laws of Human Nature by Robert Greene

Robert Greene is a master strategist in his own right and perhaps the best of our generation. This book is the culmination of his lifetime of work on power, influence, and mastery. It’s an instructive guide to human nature based on historical accounts and evidence, rather than a particular viewpoint or moral judgment. 

As Greene, emphasizes throughout the book, a deep understanding of human nature is advantageous for countless reasons. It helps you grow into a strategic observer, become a better judge of character, outthink malicious people, develop greater empathy, and realize your potential.

True to form, Greene pulls stories from both sides throughout history – those who have succeeded and those who have failed in spectacular fashion. It’s an incredible resource if you want to hone your strategic mind and it will pay immediate dividends in your own life, no matter your position. 

2) The Tigress of Forlì by Elizabeth Lev

The biography of Renaissance Italy’s most courageous countess, Caterina Sforza. Her tale is one of clever strategy, boldness, and determination. Sforza’s entire life reads like a storybook, as she fights off her husband’s assassins, the French Army, and Cesare Borgia. 

Sforza is an archetype of a dimensional thinker who was able to consider second and third-order consequences at every pivotal moment. And this was how she fought her way through life, outthinking and outmaneuvering every adversary and obstacle she came across. 

Throughout her life, powerful men viewed her as a pawn on the chessboard of Italian politics. They doubted her ability to rule and refused to take her seriously. She would prove this to be foolish, time and time again. It’s a fascinating and inspiring biography one of history’s most underrated strategic leaders. 

3) Meditations by Marcus Aurelius

A cornerstone of Stoic philosophy. At its core, it’s about the art of living. This is the true value of practical, functional philosophy. And there’s no better starting place than Marcus Aurelius. 

If you want to be more strategic, you need a bedrock of principles that you can call upon at any moment. You must also have a strong understanding of your sphere of influence – what’s within your control, what’s beyond, and what falls in-between. Stoic philosophy and the frameworks emphasized in Meditations are one of the best places you can start. 

4) Endurance: Shackleton’s Incredible Voyage by Alfred Lansing

A brilliant tale of survival that documents Sir Ernest Shackleton’s failed voyage to cross the Antarctic. Shackleton was a compelling, larger-than-life figure who offered lessons in leadership and strategy at each turn.

The book also contains one of my favorite passages. And it speaks directly to strategy and thoughtful action: “Whatever his mood – whether it was gay and breezy, or dark with rage – he had one pervading characteristic: he was purposeful.” If you want to sharpen your strategic mind, that’s what you’re after. Every action should have intention.

Shackleton’s most profound lessons are revealed in his ability to transcend the fundamentals and shift strategies as the situation required. There are few men who faced more dire circumstances than Shackleton and his crew, and who survived without any casualties. While you can’t separate luck, there was a strong level of strategy required to come out on the other side. 

5) Skin in the Game by Nassim Taleb

One of the great things about Taleb is that he challenges standard conventions and long-held beliefs about a range of topics. As a result, you’re guaranteed to walk away with a new perspective. Here he picks apart the way we think about uncertainty, symmetry, risk-sharing, and rationality in complex systems.

In terms of strategy, Taleb emphasizes the importance of thinking in high dimensions and evolving beyond the shallow. He also digs into how acting by removing is more powerful and less error-prone than acting by addition. This has implications in terms of unnecessary complexity in both our lives and how we think about strategy.

But the core of the book focuses on ethics and morality. Skin in the Game is about putting yourself out there and taking risks of your own. It’s immoral to keep the upside and transfer the downside to others. Besides, it’s impossible to understand the world and develop your own strategic abilities without putting yourself out there and taking risks of your own. 

The best strategic thinkers have grown from the chaos they’ve faced and developed resilience. Strategy isn’t about accruing power and sitting back while others take the risk. It’s about using long-term thinking to improve your position and build your capacity to give more back to the world. At its core, strategy is about taking calculated risks for the things you care about most – thoughtful action.