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. 

9 Tactics to Help You Create More, Consume Less

When it comes to remarkable leaders, artists, scientists, and entrepreneurs, each individual has their own set of principles. But there is one underlying strategy that remains constant, revealing itself in different shades across each person–creating more and consuming less.

It’s through the work you put out into the world and the way you live your life that you build a sense of meaning. Smart creatives understand this in a deep way. By creating more, you claim a larger part of yourself.

Strategies like this help build energy, establish your identity, and inform the tactics you put in place. While it takes shape in different mediums, the overall strategy is to create more and consume less. It’s the mental framework which informs smaller decisions throughout the day.

Tactics are the individual pieces that comprise the larger whole. They differ in that they require an initial investment up front. It’s what you dedicate time and energy to on a daily basis to reinforce your strategy.

Author and habit expert, James Clear, explains habits as the individual votes you cast each day for a certain identity. The same concept applies here. Tactics are the individual votes you cast each day for a certain strategy. If your strategy is to create more and consume less, you need tactics to help encourage both.

1) Make it difficult to do the easy thing (consuming)

Adding resistance can be a powerful tactic. You want to make it harder to mindlessly consume. If you struggle with Netflix, unplug the television or sign out of your account after each use. If you struggle with social media, change your passwords at the start of each week and sign out of your accounts so you can’t easily access them.

It’s amazing how impactful it can be to move things out of plain sight. Whatever’s undermining your creative energy, add more resistance so you can redirect that towards something you find greater meaning in.

2) Make it easier to do the difficult thing (creating)

This is about environment design. Building something from nothing is difficult enough as is, don’t make it any harder on yourself. Prioritize time and space for your craft to reach a deeper level of focus and creativity.

For years, my place for creativity at home–where I would sit down to write–was a couch that faced the television in my living room. And to further compound the problem, I wasn’t attempting this during quieter hours of the day. It was while people were coming and going, stopping to watch Netflix, sitting down for a meal. There were incessant distractions.

But this past year, I carved out physical space dedicated to writing. I converted one of our bedrooms to a writing studio/library and it’s made a significant difference. I also started writing first thing in the morning while my mind is fresh and I have two quiet hours before work.

Dedicating time and space where you can focus without interruption on your craft will allow you to grow exponentially faster. It’s the first step towards taking yourself and your art seriously.

Make it easier to do the right thing. This doesn’t mean sitting around waiting for ideal conditions or until you’re completely prepared, otherwise you’ll be waiting forever. It means setting yourself up for success through the things you can control in your immediate environment.

3) Pair positive reinforcements

Four years ago, when I first started taking writing seriously, I paired my writing sessions with my favorite coffee shop in Nashville. I walked over in the evenings after work to sit down and write. It’s something I looked forward to every day because of the atmosphere, the music I would listen to and, of course, the caffeine. This reinforcement helped me rediscover writing as a creative outlet.

Now I automatically associate these cues with my creative process. Coffee, coffee shops, and ambient music are shortcuts that jump me into a state of relaxed concentration that I need to do my best writing.

4) Allow yourself to get stuck

At the first sign of boredom or discomfort, most of us instinctively search for distractions and outlets for immediate gratification. And we do so without even recognizing it.

Until recently, the moment I slowed down or felt stuck in my own writing, I coped by jumping between tabs in Chrome–checking email, looking up restaurants for dinner, scrolling through Twitter.

The secret is to allow yourself to get stuck and sit with something. Once I gave myself permission to sit there without looking away, my resilience and creativity improved immediately.

Momentum is easier to come by when you don’t look away at the first challenging moment. Bouncing between distractions won’t result in some magical insight. Give yourself permission to get stuck.

“Too many people believe that everything must be pleasurable in life, which makes them constantly search for distractions and short-circuits the learning process. The pain is a kind of challenge your mind presents–will you learn how to focus and move past the boredom, or like a child will you succumb to the need for immediate pleasure and distraction.”

— Robert Greene

For writers: Tools aren’t everything but they can be helpful. I’ve found Ulysses to be one of the best investments I’ve made ($5/month). It helps facilitate each of these first four tactics. Its typewriter mode is fullscreen which makes it easier to focus, harder to jump between distractions (web, email, text messages), and the daily goals feature helps create a strong positive reinforcement.

5) Create a distraction-free phone

For most of us, myself included, our phones are our number one source of distraction. Jake Knapp and John Zeratsky outline the tactic that is a distraction-free phone in their book Focus. It’s one of the most influential tactics I’ve found in the past year. There are three main components:

1. Delete infinity-pools apps (social media) from your phone

2. Delete email accounts from your phone

3. Delete/disable the web browser on your phone

These might sound extreme, but let me explain. Last year I took step one, deleting infinity-pools apps (sources of never-ending streams of content). But the energy I wasted on social media was replaced by checking email, random websites, and Googling everything that crossed my mind.

It was only after I took steps two and three, despite my initial reservations, that I saw a measurable difference in my focus and creativity. There’s now far less clutter and distraction in my day-to-day. As a result, the clarity of my thoughts has improved and I have more opportunities to create.

I recognize this might strike terror in you. But test it out for a week and see how it goes. I no longer reach for my phone as a crutch in moments of boredom. And it taught me how many meaningless things cross my mind and how few emails (zero) require an immediate response.

6) Keep a journal instead

If you cut the time spent on your phone in half and replaced that with journaling, you’d improve your balance between creating and consuming within a matter of days. I leave a journal sitting on the table of whichever room I’m in at home. I jot down ideas as they come to me, intentions in the morning, reflections in the evening, beginnings of articles, and whatever else captures my curiosity.

The act of writing on paper allows you to explore concepts and draw connections in ways that you can’t on a screen. Your ideas take on a different dimension. Not to mention the fact that it eliminates the threat of distractions you face on a phone, tablet, or computer.

But the biggest advantage of journaling is that it helps build awareness. By reflecting, you gain insight into your own behaviors and tendencies, rather than wandering through life on autopilot. If you want to create more and consume less, you have to start by recognizing what you’re doing well and where there’s room to improve.

7) Use art as inspiration

This is not to say that you shouldn’t appreciate other people’s work. But you should use it as inspiration to create something of your own. Actively engage in the things you’re watching, reading, listening to, and consuming. Try to engage, form connections, and draw insights of your own. (Check out my book notes on 70+ titles for an example of how I approach this while reading.)

Use books, films, documentaries, paintings, research, and keynotes as inspiration to create more. If you’re a writer, weave one of the connections you made into your next article. If you’re an entrepreneur, adapt one of the stories to your current project and share it with your team to build stronger engagement.

The goal is to create an active mental landscape that’s alive with hundreds of connections. It directly benefits your creativity and craft when you’re able to combine ideas across disciplines in new and interesting ways.

8) Start small

Don’t go off the deep end and commit to twelve hours of creating each day. You’ll burn yourself out before you ever get started and make it difficult to recover. Instead, begin from a more sustainable place.

If you want to write more music, start with fifteen minutes each day then build from there. That’s how you create momentum. Develop habits that are sustainable and allow them to grow steadily over time.

Remind yourself that growth is nonlinear. Don’t expect immediate results. People tend to overestimate what they can accomplish in the short-term and underestimate what they can accomplish over the course of years. The power of small, calculated decisions and tactics grows exponentially over time. Start small and let compound interest run its course.

9) Find a medium that resonates with you

While every remarkable mind shares some sense of this strategy to create more and consume less, the medium varies. For J.K. Rowling it’s writing, Jay-Z it’s music, Scott Belsky it’s design and technology, Alexander von Humboldt it was exploration and science, Leonardo da Vinci it was art and engineering.

If you need a better starting place, consider the medium that resonates with you. Robert Greene, author of The Laws of Human Nature, suggests reflecting on three areas to help with this:

1. Inclinations in your earliest years–moments of fascination with certain subject, objects, or activities.

2. Moments when certain tasks or activities felt natural to you.

3. Particular forms of intelligence your brain is wired for.

The key is determining what’s meaningful to you and not absorbing what’s important to someone else as your own. Otherwise, you’ll miss the mark.

This is perhaps the most difficult skill of all–sorting through the noise and determining your own sense of authenticity. This requires years of exploration and reflection to determine for yourself. But it’s the only way to sustain a creative mindset and find meaning in your work.

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As a rule of thumb, it’s better to lean towards the mentality of a strategist than a tactician. Those who have the patience to expand their perspective of time and the endurance to play the long game put themselves at a significant advantage. There are multiple paths and hundreds of tactics you can use you reach the end goal.

These tactics are meant to help you find your own starting place. Use them to create momentum and discover what works best for you. Experiment and remain flexible. There’s no correct path or proper sequence of decisions. What matters is that the overall strategy to create more and consume less is held in constant focus.