I want you to imagine, just for a moment, that
you have dedicated your entire existence to a
single, singular definition of success. You've
risked your life for it, you've begged for money
for it, and you've dragged yourself through the
literal worst weather on planet Earth for it.
And then, when you are tantalizingly close, I'm
talking within touching distance, close enough
to feel like you've already won, you stop, you
turn around. And you walk away. It sounds like
a nightmare scenario. In our current culture,
that's a failure. You didn't ship the product.
You didn't close the deal. You didn't win the
gold. Exactly. But here is the kicker, and this
is why we are here today. Because of that decision
to walk away, this man is remembered not as a
quitter, but as arguably the greatest leader
who ever lived. It is a massive paradox. If you
look at his resume on paper, strictly by the
metrics of his era, it reads like a list of catastrophes.
He never reached the South Pole. He lost a ship
in the ice. He died essentially broken in debt.
And yet, if you go to a management seminar today
or talk to military historians or even just,
you know, look at who modern astronauts admire.
They don't look to the guys who planted the flags.
No. They look to the man who failed. Today, we
are doing a deep dive into the life. the near
deaths and the enduring legacy of Sir Ernest
Shackleton. And we have a serious stack of sources
to get through. We do. We've got the biographies.
We've got the expedition logs from the discovery,
the Nimrod and, of course, the famous endurance.
And we're even pulling in the very recent news
about the rediscovery of his lost ships, which
adds a whole new layer to the story. Our mission
here is really to unpack that paradox he started
with. We are going back to the heroic age of
Antarctic exploration, which, let's be honest,
was a time when going south is basically like
going to Mars. But with wool sweaters instead
of spacesuits. Exactly. And no radio contact.
We want to understand how a restless Anglo -Irish
merchant Navy officer became the person you pray
for when disaster strikes. There's the famous
quote about that, which we have to save for later
because it's just too good. But for you, our
listener, as we wait. into this I want you to
think about this not just as history this is
a master class in resilience in the art of knowing
when to quit which nobody teaches us and how
to manage a team when you were stuck in a frozen
hellscape for two years with no hope of rescue
it really is the ultimate case study in crisis
management But to understand the manager and
to understand why he made the choices he did,
we have to understand the man. Because Shackleton
was not your typical Edwardian explorer. No.
He didn't fit the mold. Right. Let's unpack his
background. Because when I picture a British
explorer from the early 1900s, I have a very
specific archetype in my head. Stiff upper lip.
Yes. Stiff upper lip, background at Eton or Harrow,
and a commission in the Royal Navy. Very aristocratic.
But Shackleton was a bit of an outsider, wasn't
he? He was, and that outsider status is absolutely
key to his leadership style. He was born in 1874
in County Kildare, Ireland. So right off the
bat, he has this Anglo -Irish heritage. His father
was a farmer who eventually retrained as a doctor
and moved the family to London when Ernest was
10. But the young Shackleton? He just didn't
fit into the academic box. He wasn't a school
person. Not at all. He was bored by school. He
was a voracious reader. He could quote Keats
and Browning at length. But he hated the structure
of formal education. So he skips the university
road entirely. Completely. At 16, he joins the
Merchant Navy. We need to pause here because
the distinction between the Merchant Navy and
the Royal Navy in Victorian England is massive.
Right. It's not just two different fleets. It's
two different social universes. Break that down
for us. Why does that matter so much? Well, the
Royal Navy, which is where his future rival Captain
Scott came from, was incredibly hierarchical.
It was rigid. You had the officers who were gentlemen
and you had the crew and never the twain shall
meet. A huge class divide. A chasm. Discipline
was top down. But Shackleton goes into the merchant
service. He learns his trade before the mast
on sailing vessels. That means he's hauling ropes.
He's scrubbing decks. He's eating the same terrible
food as the deckhands. He is mixing with people
from all walks of life, all social classes. So
he's getting a real world education in human
nature. He's not just issuing orders from a bridge.
He's, you know, seeing how the sausage is made,
so to speak. That's a perfect way to put it.
He learned how to handle men not by pointing
at a rank badge, but by personality. by influence
he saw what made men work hard and what made
the mutiny by the time he joins the union castle
line and eventually talks his way onto his first
antarctic expedition he has a very different
world view than his contemporaries he's rougher
perhaps but also significantly more adaptable
and he creates this opportunity for himself by
talking his way onto the discovery expedition
in 1901 This is led by Captain Robert Falcon
Scott. Yes. This is the big leagues. This is
the British National Antarctic Expedition. But
this is also where the trouble starts, isn't
it? It is. And it sets the stage for everything
that follows. The Discovery Expedition was run
on strict Royal Navy lines. Shackleton was the
third officer. He was charismatic. He was funny.
And he was popular with the crew, maybe a little
too popular for Scott's liking. Scott was a bit
more introverted, a bit more rigid. It sounds
like a personality clash waiting to happen. It
was. But they, along with Edward Wilson, make
a push for the South Pole. They set a new farthest
south record, getting to 82 degrees, 17 minutes
south. Which, to be fair, is a huge achievement
for the time. It was massive. But the journey
itself was a disaster. They didn't understand
nutrition, so they had scurvy. Right. They didn't
really understand how to manage the dogs, so
the dogs died. And on the return trip, Shackleton
physically broke down. He had severe respiratory
issues, likely exacerbated by the scurvy. He
had to be helped and at times carried on the
sledge. That must have been deeply humiliating
for him. Oh, incredibly so. And when they finally
got back to the ship, Scott made a decision.
He sent Shackleton home early on the relief ship.
Ouch. The send home card. Yeah. That has to sting.
It was a career ender, potentially. Scott cited
health grounds, saying Shackleton shouldn't risk
another winter. But there has always been speculation,
and our sources point to this heavily, that Scott
was perhaps jealous of Shackleton's popularity.
Or just didn't like his style. Or just found
his informal style irritating. There's a report
that Scott told the ship's doctor, if he doesn't
go back sick, he will go back in disgrace. Wow.
So he's basically kicked off the team. That creates
a serious chip on the shoulder, doesn't it? Oh,
yeah. That's the fuel. Precisely. He returns
to England, not as a conqueror, but as a man
with something to prove. He feels he was pushed
out. He needs to return to the Antarctic. He
needs to outdo Scott. He needs to show the world
and Scott that he is capable of the prize. And
this leads us to the Nimrod Expedition of 1907.
Okay, let's look at Nimrod, because I feel like
everyone talks about the endurance, and we will...
Trust me, we will get there. But the Nimrod expedition
contains maybe the most badass decision in exploration
history. It's certainly the most heartbreaking
and arguably the most mature decision ever made
on the ice. So Shackleton raises the money, mostly
from wealthy friends and loans he couldn't really
afford. Right. He was always hustling for cash.
Always. And he goes back. His goal is the pole.
Simple as that. And they do incredible things
on this trip. I was reading they climbed Mount
Erebus, which is an active volcano. In Antarctica?
Yes. A team climbed Erebus, an astonishing feat.
They also located the South Magnetic Pole. But
the main event was the Great Southern Journey.
Shackleton and three companions, Frank Wilde,
Eric Marshall, and Jameson Adams, march south.
Okay. They discover the Beardmore Glacier, which
is this massive gateway to the polar plateau.
They are the first human beings to ever set foot
on the south polar plateau. They are walking
into the absolute unknown. And they get close.
How close are we talking? They make it to 88
degrees, 23 minutes south. That is 97 miles from
the South Pole. 97 miles. That is, I mean, in
a car, that's an hour and a half on the highway.
It's nothing. Even walking, that's a few days.
They were right there. They had marched hundreds
of miles. They were closer than anyone had ever
been. They could probably see the sky changing
over the pole. But they were starving. They were
running on half rations. And they were exhausted.
They were literally dying on their feet. Most
people, driven by that kind of ego and ambition,
having come that far, would have gambled. They
would have said, we'll find a way. Let's just
get there. Scott likely would have gone on, but
Shackleton stopped. He did the math. He realized
they had enough supplies to get to the pole,
but not enough to get back. So they would plant
the flag, claim the glory. And then they would
be dead bodies on the return journey. So it's
a choice between a glorious death. Or a shameful
survival. Yeah. Or what some would call a shameful
survival. Exactly. On January 9, 1909, Shackleton
made the decision to turn back. He wrote in his
diary about the decision, but the most telling
comment came later when he was back in England
talking to his wife, Emily. She asked him about
it, and he simply said, A live donkey is better
than a dead lion, isn't it? A live donkey is
better than a dead lion. That is such a powerful
summary of his philosophy. The goal matters,
but people matter more. And the return journey
proved he was right. It was a race against death.
There's this incredible anecdote from the diaries
involving Frank Wilde to illustrate just how
close they were to the edge. Wilde was sick,
basically dying of dysentery and starvation.
At one point, Shackleton took his own daily ration,
a single biscuit, and forced Wilde to eat it.
One biscuit. One biscuit. But in that environment,
that biscuit is life. Frank Wilde wrote in his
diary, all the money that was ever minted would
not have bought that biscuit. And the remembrance
of that sacrifice will never leave me. Wow. That
is the loyalty Shackleton inspired. He didn't
just command, he sacrificed. He managed the team
by serving the team. So he comes back a hero.
He's knighted. He's Sir Ernest Shackleton now.
Yeah. But he didn't reach the pole. And then
the worst thing happens for his ambition. Roald
Amundsen, the Norwegian, beats everyone to it
in 1911. Yep. And then Scott gets there a month
later and dies on the way back. The race is over.
Exactly. The prize is gone. The map is filled
in. So what does a restless explorer do? He moves
the goalposts. He invents a new prize. Shackleton
conceives of the Imperial Trans -Antarctic Expedition.
If he can't be the first to the pole, he will
be the first to cross the entire continent from
sea to sea, passing through the pole. This is
the setup for the endurance. And I love the stories
about the recruitment for this. We have to address
the elephant in the room that Famous had. It
is a legendary ad. It's quoted in marketing textbooks
everywhere. It's on motivational posters. The
only problem is our sources suggest it's likely
a myth. No. I wanted that to be true so bad.
I know. I know. It captures the spirit perfectly.
But researchers have scoured the newspapers of
the time and haven't been able to find the original
copy. Okay. Okay. But even if the ad isn't real,
the response was right. Oh, yeah. What isn't
a myth is that he had over 5 ,000 applicants.
5 ,000 people signing up for what sounds like
a miserable time. Yeah. And his interview process
was unique. Very eccentric. He wasn't looking
for technical skills alone. He was looking for
temperament. He asked Reginald James, the physicist,
if he could sing. If he could sing. For a polar
expedition. Yes. Because Shackleton knew that
being stuck in a tent for six months with a guy
who is annoying or depressive is more dangerous
than the cold. That makes so much sense. He needed
morale. He needed good tent mates. He asked others
just one or two questions and hired them on a
hunch. He was casting a reality show as much
as he was hiring a crew. He knew that technical
skills can be taught, but personality is fixed.
Exactly. He selected 28 men for the Endurance.
They set sail in 1914, just as World War I is
breaking out. Right. I read that he offered his
ship and crew to the government for the war effort.
He did. But Winston Churchill, who was first
Lord of the Admiralty then, told him to proceed.
So they head south. They enter the Weddell Sea.
And this is where the endurance meets its match.
The Weddell Sea is notoriously dangerous. It's
a gyre, which means the currents swirl the ice
around and pack it tight against the Antarctic
Peninsula. A natural ice trap. And the ice conditions
that year were terrible. By January 1915, the
ship becomes frozen fast in an ice flow. They
are stuck. They can't move forward. They can't
move back. They are drifting north with the pack
ice. And this is where the leadership really
kicks in, because I imagine you are stuck on
a wooden ship. It's freezing. The sun is going
down for the winter. Morale could tank very,
very quickly. That was Shappleton's biggest fear.
Depression, boredom, and cliques. So he converted
the ship into a winter station. He kept the hierarchy
loose. Ah, back to his merchant navy roots. Exactly.
He made the scientists and officers scrub the
floors alongside the sailors again, breaking
down those class barriers. He organized theatrical
performances, soccer games on the ice, dog sled
races. He kept them busy and he kept them social.
He was constantly monitoring the mental temperature
of the crew. He was managing their minds as much
as their survival. He was. But the ice doesn't
care about morale. In October 1915, the pressure
from the ice became too much. The flows started
to crush the hull. It sounds terrifying in the
diaries. The sound of massive timber snapping
like matchsticks, the rigging screaming. I can't
even imagine. Shackleton realizes the ship is
lost. He gives the order. Abandon ship. They
move their supplies onto the ice. And then in
November, the ship sinks. It just slips under
the ice. There is a moment there that defines
the whole expedition. The ship, their only link
to civilization, their warmth, their safety disappears.
They are standing on a frozen sheet of ocean
thousands of miles from help with no radio. Panic
would be the natural reaction. Terror. It would
be. But Shackleton gathers the men and calmly
says, ship and stores have gone, so now we'll
go home. So now we'll go home. Like it's just
a change of itinerary. He immediately reframed
the disaster. It wasn't we are doomed. It was
we have a new mission. He didn't let them dwell
on what was lost. So they are camping on ice
floes. The ice is melting as summer approaches.
They're drifting. This goes on for months. This
is the part of the story that gives me anxiety
just reading it. It's terrifying. You are sleeping
on a sheet of ice that could crack open under
your tent at any moment. And it did crack. The
flow started breaking up in April 1916. Shackleton
realizes they have to move or they will fall
into the ocean. They load into the three small
lifeboats they salvaged from the Endurance. They
are aiming for Elephant Island, a desolate rock
about 100 miles away. And this boat journey.
Five days in open lifeboats in Antarctic waters.
It was harrowing. They were soaked, freezing,
dehydrated. They had saltwater boils. They were
rowing through pack ice, dodging killer whales.
When they finally landed on Elephant Island,
it was the first time they had stood on solid
land in 497 days. 497 days. Imagine the relief.
But Elephant Island isn't exactly a resort, is
it? It's a bleak, inhospitable rock. It's far
outside any shipping lanes. It's covered in penguin
guano and swept by gales. Nobody was coming to
look for them there. No. Shackleton realized
that if they stayed, they would starve and die.
He had to go get help. And this leads to the
voyage of the James Caird. This is the part that
historians usually point to as the greatest small
boat journey ever undertaken. Without a doubt.
Shackleton takes the largest lifeboat, the James
Caird. It's only 20 feet long. He takes five
men. Captain Worsley, the navigator, Tom Crean,
the carpenter Harry McNish, and two others, Vincent
and McCarthy. Okay. They have to sail 800 miles
across the roughest ocean in the world, the Southern
Ocean, in winter to reach the whaling stations
on South Georgia. 800 miles. Yeah. In a 20 -foot
boat with hurricane force winds. And waves the
size of houses. We are talking about the furious
50s. The waves are rolling around the globe unimpeded.
And the navigation. I mean, what Orsley did was
a miracle. How did he even do it? He was navigating
by catching momentary glimpses of stars through
the storm clouds. He had to stand up, braced
by two other men, and try to use a sextant in
a boat that was bucking like a rodeo horse. If
he's off by even a degree. If he was off by even
a degree, they would miss the island completely.
Next stop. Antarctica, or oblivion, they would
be swept out into the Atlantic to die of thirst.
There's a detail in the source material about
a storm they survived that actually sank a 500
-ton steamer nearby. That's right, a 500 -ton
ship. And they survived in a lifeboat. At one
point, they thought they saw the sky clearing,
a line of white light. Shackleton called out
that it was clearing. But then he realized it
wasn't the sky. It was the white foam of a massive
rogue wave. That is terrifying. He yelled, hold
on, it's got us. They were buried in water. The
boat was half swamped. They were bailing for
their lives with sleeping bags, pots, anything
they could grab. And it held together. The boat
held together largely because McNish, the carpenter,
had improvised a decking out of sledge runners
and canvas. before they left? The carpenter,
McNish. He is a difficult character, wasn't he?
He'd rebelled earlier on the ice. He had. He
was a grumbler, a bit of a mutineer. But Shackleton
took him on the boat because he knew he needed
the best carpenter. And he also knew it was better
to keep a troublemaker close where he could watch
him rather than leave him behind to praise him
the morale of the main group. Smart. So they
make it. They spot South Georgia. But of course,
because nothing can be easy for Ernest Shackleton.
Never. They land on the wrong side of the island.
Right. They crash land in King Hakon Bay. The
boat is battered. The rudder is gone. The whaling
stations and the people are on the other side.
Between them lies the interior of South Georgia.
Uncharted glaciers, jagged peaks, snow fields.
And nobody had ever crossed it. No one. And they
can't sail around, so they have to walk. Shackleton,
Worsley, and Tom Crean. They leave the other
three, who are too weak to walk, under the overturned
boat on the beach. The three men set off. They
have no climbing gear. Nothing. They took screws
from the lifeboat and put them into the soles
of their boots for grip. Improvised crampons.
I love that detail. It's so MacGyver. They hiked
for 36 hours straight. If they stopped to sleep,
they would freeze. They had to make decisions
on the fly. At one point, they were trapped on
a ridge with night falling and fog rolling in.
They couldn't stay and they couldn't climb down.
So they sat on coils of rope like sleds and launched
themselves into the fog. A leap of faith. Literally.
They slid down 2 ,000 feet in a few minutes.
If there had been rocks at the bottom, they would
have died. But it leveled out into a snowbank.
And this trek is where the third man factor comes
in. Yes. Tell us about that. This feels almost
supernatural. Later, all three men independently
admitted that they felt a presence. They felt
like there were four of them, not three. Four
of them? Yeah. Worsley said he often found himself
counting the party and getting to four. It's
a phenomenon often reported by people in extreme
survival situations. The sense that something
or someone is guiding you. Whether it was a hallucination
from exhaustion or something else, it got them
there. They hear the steam whistle of the whaling
station. That sound must have been the sweetest
music they ever heard. I can only imagine what
the station manager thought when these three
wild -looking men, black with blubber smoke,
hair matted, clothes in rags, walked out of the
mountains. The station manager asked, Who the
hell are you? And Shackleton replied, My name
is Shackleton. It must have been a ghost story
come to life. Everyone in the world thought they
had died two years ago. But the mission wasn't
over. He had left three men on the other side
of South Georgia and 22 men. back on Elephant
Island. And this is where Shackleton's tenacity
is just relentless. He doesn't rest. He doesn't
take a week off. He picks up the three on the
other side of South Georgia immediately. But
getting to Elephant Island was harder. The pack
ice was still thick. He tried with a whaler blocked
by ice, tried with an Argentine ship blocked,
a British schooner engine trouble. He's failing
over and over. And meanwhile, the men on Elephant
Island have been there for four months. They're
living under upturned boats, eating penguins,
staring at the horizon. They have no idea. They
don't know if Shackleton survived. Finally, he
gets a tug from the Chilean Navy, the Yelcho.
It wasn't an icebreaker. It was a small tug.
But he pushes through. On August 30, 1916, four
months after he left them, Shackleton breaks
through the mist. He counts the figures on the
beach through his binoculars. He turns to Worsley
and says, they are all there. They are all there.
Not a single life lost among the endurance crew.
It's the miracle of the age. Now, we should note
for accuracy, there was a support party on the
other side of the continent, the Ross Sea Party,
who were laying depots for the crossing that
never happened. Right. They did lose three men,
including their commander. So the expedition
as a whole was not without casualty. But the
survival of the endurance crew under Shackleton's
direct command is flawless. So he comes back
to civilization. But the world has changed. It's
1916. The First World War is slaughtering millions.
Shackleton returns. And suddenly his survival
story, while amazing, is overshadowed by the
massive loss of life in Europe. He felt very
out of place. He was an Edwardian hero in a modern
mechanized war. He was too old for conscription,
though he volunteered. He served in northern
Russia for a bit during the Civil War intervention
there. But he was restless. His business ventures
failed. He was heavily in debt. Terribly in debt.
He was a man who only really made sense on the
ice. It's like he couldn't function in normal
society. He needed the crisis to feel alive.
Exactly. So in 1921, he launches one last expedition.
The Quest expedition. It was vague in its goals,
oceanography, sub -Antarctic islands, but really
it was just an excuse to go back, to go home
to the South. But his health was failing. He'd
been hiding heart problems for years, hadn't
he? Yes. He had suspected heart issues even back
in the Nimrod days. On the way south with the
Quest, he had a heart attack in Rio but refused
to stop. They arrived at South Georgia, the scene
of his greatest triumph, on January 4, 1922.
And there's a poignant conversation with the
ship's doctor. Yes. Macklin was called to Shackleton's
cabin in the middle of the night. Shackleton
was in pain. Macklin told him he needed to change
his lifestyle to stop overworking to take it
easy. And Shackleton's response is just perfect.
It is. He looked at him and asked, You are always
wanting me to give up things. What is it I ought
to give up? Macklin said, Chiefly alcohol, boss.
Moments later, Shackleton suffered a massive
heart attack and died. He was 47. 47. That is
incredibly young. He literally gave his heart
to the Antarctic. His wife, Emily, asked that
he be buried there on South Georgia. So he lies
there today among the whalers. It's a fitting
end. Now let's talk about the legacy. Because
when he died, he wasn't considered the top explorer,
right? Scott was the golden boy. For a long time,
Scott was the Victorian ideal, the tragic hero
who died for his country. Shackleton was respected,
but he was seen as a bit of a maverick, maybe
a bit chaotic. A brilliant failure, maybe. Exactly.
But in the later 20th century, the narrative
flipped. We started to learn more about Scott's
rigidity, his mistakes with the dogs and ponies,
and simultaneously, we started to value Shackleton's
adaptability. It's the shift from valuing heroic
death to valuing survival and emotional intelligence.
Precisely. Business schools started using Shackleton
as a case study, how to build a team, how to
pivot when the strategy fails, how to maintain
hope. He became the model for modern leadership.
And there is that quote by Raymond Priestley,
who knew both men. I teased it in the intro.
Yes, it's the best summary of all, Priestley
said. Scott for scientific method, Amundsen for
speed and efficiency. But when disaster strikes
and all hope is gone, get down on your knees
and pray for Shackleton. That gives me chills.
It's the acknowledgement that when the plan goes
out the window, you don't want the guy who follows
the rulebook. You want the guy who can improvise.
And his legacy has been very tangible recently.
In 2022, the Falklands Maritime Heritage Trust
found the wreck of the Endurance. It was 3 ,000
meters down in the Weddell Sea. And it looked
pristine. I saw the photos. The cold water preserved
it. You can still read the name on the stern.
It's incredible. The Antarctic waters don't have
the wood -eating worms that destroy ships elsewhere.
It looks like it sank yesterday. And just recently,
in June 2024, they found the wreck of the quest,
his final ship, off the coast of Newfoundland.
Wow. So even the physical remnants of his life
are resurfacing. It's keeping the story alive.
It feels like he's still with us, in a way. So
bringing this all back to the listener, what
does this mean for us? We aren't stuck on ice
flows, hopefully, but we all face failures. We
all have projects that sink. Shackleton teaches
us that the goal isn't the only thing. He failed
at the pole. He failed at the crossing. But he
succeeded at the human element. He brought his
people home. That was his real success. That
was his true north. He realized that a live donkey
is better than a dead lion. It's a lesson in
redefining success. Sometimes success is just
surviving the storm with your humanity intact.
And looking at your own failed projects, maybe
the business that didn't launch or the career
path that dead -ended, and asking, did I get
the people out alive? Did I learn? Was there
a success hidden inside the failure? Exactly.
Shackleton proves that you can lose the ship,
lose the money, lose the race, and still win
the history books if you lead with empathy and
resilience. A fascinating figure. A failure and
a legend. Sir Ernest Shackleton. That's it for
this deep dive. But before we go, I want to leave
you with one thought to mull over. We mentioned
the third man, that presence that guided them
across the mountains. We usually dismiss it as
hallucination or stress. But in a world that
is increasingly data driven and logical, Shackleton's
story reminds us that there is a spiritual, almost
mystical component to human endurance. When we
are at our absolute limit, when we have exhausted
all our resources, do we tap into something else?
Was it just brain chemistry or was it the ultimate
manifestation of the will to live? Something
to think about next time you're pushing through
your own. impossible journey thanks for listening
we'll catch you on the next dive