Leadership lessons from the bottom of the world

Sir Ernest Shackleton and his ill-fated Endurance voyage have a lot to teach us about resilience, loyalty and leadership

View of the expedition boat I was on near South Georgia

This post was originally posted in my Forbes column here.

I recently returned from Antarctica (which, given Omicron and the new year, feels like an eternity ago). I learned so much about the 7th continent. But one explorer’s story marked me more than others, and taught me some important (startup) leadership lessons.

First some context: all our knowledge of this seventh continent is surprisingly recent. The age of explorers to the South Pole was in the 20th century, with storied names like Sir Ernest Shackleton, Roald Amundsen, and Robert Scott.

In many ways, Antarctic explorers were entrepreneurs of their day. They raised capital for expeditions. They commissioned new ship designs for unforgiving environments. They built teams to venture into the unknown. Their expeditions faced incredible odds – Antarctica is home to the coldest known temperatures on the planet, six months of darkness, and unnavigable seas filled with melting and reforming ice floes.

Their leadership lessons offer us some important wisdom for fintech and entrepreneurial leaders. First among them is Sir Ernest Shackleton, and particularly his experience on the Endurance (his ship). His mission was to reach the South Pole by foot. Spoiler alert: he did not succeed. But his feat remains one of the world’s greatest examples of leadership, perseverance and survival in modern history.

First, the short story

In August 1914, Sir Ernest Shackleton headed out on his third expedition to the Antarctic. His ship, the Endurance, was the latest design in ice exploration. He was well prepared and had a motivated crew.

Leaving South Georgia (the last port of call) in December 1914, he made it to the Weddell Sea. But as the expedition advanced, the ship was caught in pack ice and unable to make further progress. By February, at the end of the Antarctic summer, the ship was fully iced in. In August, facing mounting ice pressure, the ship was crushed and sank.

Without a ship, the crew was forced to camp on ice floes in the middle of nowhere waiting for the ice to melt. That came on April 9th of the following year, when the ice cracked, and they launched the rescue boats. After 6 nearly sleepless nights, they finally made landfall on Elephant island: an inhospitable spit of land, with limited fresh water, no greenery and some migratory wildlife. It had already been 497 days since their last land fall.

Being so remote, Shackleton knew they would never be found. He set out again with a smaller party to find help. Over 16 days in effectively a dinghy, he sailed 800 miles of open ocean to South Georgia, home to various outposts.

But here again he was stymied. They landed on the opposite side of the island to the manned whaling stations, and could not get around by sea. He took an even smaller party to traverse the island – home to some of the world’s most technically challenging peaks and glaciers - by foot. Their traverse took 36 straight hours, clambering over glaciers and hiking the peaks, to eventually arrive in Stromness, a whaling station on the opposite side of the island. It was the first ever recorded crossing of the island.

Five hundred days after his original departure, he was back in civilization. It took another four attempts to rescue the rest of the crew but remarkably, every single person made it out alive.

What can this incredible story of leadership, survival, resilience – and endurance – teach us about entrepreneurial (and fintech) leadership? Here are five reflections from my trip.

1. Keep a long-term and audacious vision

In South Georgia, inscribed on Shackleton’s grave is an inscription from the poet Robert Browning: “I hold…that a man should strive to the uttermost for his life's set prize.”

Inscription on the back of Shackleton’s tomb

Shackleton was not a one-time explorer. This was his life’s mission. The Endurance voyage was his third expedition to the Antarctic. His objective was audacious: being the first to cross the entire continent.

His vision was contagious. He convinced funders (including corporations and private individuals, since the Royal Geographical Society’s institutional funding had gone to his contemporary and rival, Captain Robert Falcon Scott) and his team to support him and join him because it was a massively ambitious goal.

Yet it was also built on a lifetime of experience and credibility, getting ever closer to this inspiring vision.

2. Understand team dynamics, and know individual strengths

Perhaps one of Shackleton’s greatest strengths was his focus on individual strengths and weaknesses. Even more, he understood how individual members contributed or stymied group dynamics.

For example, when selecting the rescue party to set off from Elephant Island, he did not select those he got along with best. He chose some of the more difficult characters, that he thought might cause the most discord and unrest among those left behind. He also left Frank Wilde, one of his strongest team members, to lead in his absence.

For Shackleton, team dynamics were multi-dimensional, based on multiple goals – in this case the success of the rescue party and the survival of the core party.

3. Set traditions and celebrate moments to drive culture

Shackleton invested in team culture. As Gerard Baker, a former British Antarctic Survey cook and an Expedition Leader with Arctic Tern explained it to me:

“while all of the men struggled with their predicament, it was Shackleton, and importantly Charles Green the cook that provided daily reassurance and comfort, and ultimately security. The sense of purpose of those two men was astonishing”.

Shackleton focused on important moments and traditions. He selected crew members who could play musical instruments knowing this would drive camaraderie. And even in the dark eternal winter, he would mark specific days for celebration. To give his men something to look forward to, and a connection to the outside world, celebrations like Christmas were marked with exuberant parties and fancy dress.

He also demonstrated culture by example, for instance by insisting on not being treated differently, to show that the whole group existed in solidarity. He would not receive larger food portions or be fed first.

4. Loyalty and responsibility

Shackleton demonstrated a strong sense of loyalty towards those that supported him.

First and foremost, he showed it to his men. He felt deep responsibility to getting his crew back home safely. That meant that when he got to South Georgia, he would not get a moment’s rest. He would be out, with four separate attempts to get his men.

He also demonstrated loyalty and recognition to his supporters. Shackleton named many things and places based on his backers. Perhaps the most notable is the James Caird, his lifeboat which has become famous (infamous) for making the rescue trip. It was named after a sponsor of the expedition.

5. Know when to quit and when to persevere

Shackleton knew when to take risks and when to quit. He had an innate calculus around this.

When the ship sank, his initial instinct was to traverse the ice floes on foot. Realizing this was futile, he pivoted to camping. At the top of South Georgia’s cliffs, and recognizing they risked freezing if they did not make rapid progress, he suggested a foolhardy approach of sliding down the mountain – 2000 feet. But there was no choice. Staying or even continuing to walk meant death. Sliding was a risk but provided a chance of survival.

Shackleton also knew when to quit. For example, on his second expedition to the South Pole (the one before the ill-fated Endurance) he turned around at 112 miles from the Pole, after already covering nearly 800 miles on foot. He realized he and his crew did not have the provisions or strength to reach the Pole and return to the coast again. As Gabrielle Walker, author of Antarctica: An Intimate Portrait of a Mysterious Continent,  stressed, Shackleton’s ability to pivot, and make the tough decisions was key. Shackleton once told his wife: “better a live donkey than a dead lion” when deciding to turn around short of the South Pole on his Nimrod Expedition.

Obligatory penguin photo

Conclusion

Shackleton was certainly not a perfect person. But he exhibited incredible strengths in the area of leadership; in bringing a party of people towards a seemingly impossible goal. While failing to achieve it, his story of survival was even more incredible. As Carl Shephard, founder of Insider Expeditions who led this adventure, remarked:

“it is easy to be mightily humbled and supremely inspired by Shackleton’s story as we all lead teams through challenging waters in our business endeavors.”

He has also inspired leaders around the world. I asked Ben Saunders, the world record holder for the longest ever polar journey on foot, what Shackleton’s feat meant for him:  

“Sir Winston Churchill said that ‘Success is all about going from failure to failure without losing enthusiasm’. Shackleton's Endurance reads like a catalogue of crises, yet he not only kept his own enthusiasm, but managed to convince his team to keep believing – and to keep trying their hardest – even when the odds seemed hopelessly stacked against them. To me, Shackleton remains a paragon of the virtues and abilities that comprise leadership in its most effective form.“

I hope his story inspires you.