The Decisions Nobody Wants to Make
In 1914, Ernest Shackleton set out to cross Antarctica. When the pack ice crushed his ship, he faced a series of decisions that no leader wants to make. Each decision required abandoning something he valued. Each one saved the lives of his 27 crew members.
Modern CEOs face parallel decisions with lower stakes and the same reluctance.
Decision 1: Abandon the Goal
When the Endurance became trapped in pack ice, Shackleton faced a choice. He could wait for conditions to improve and pursue the original crossing. Or he could abandon the Antarctic crossing entirely and focus on survival.
He chose survival. He publicly abandoned the mission that had consumed years of planning, fundraising, and preparation. He told the crew the crossing was over. The new mission was getting everyone home alive.
This decision required him to separate his identity from his goal. He was an explorer. Abandoning the expedition meant admitting failure. And he did it without hesitation because the goal had become incompatible with reality.
The CEO parallel: Organizations hold on to strategic goals long after the conditions that supported them have changed. The three-year plan built in a different market environment keeps getting funded because abandoning it means admitting the original plan was wrong. Leaders who cannot separate their identity from their strategy make this mistake repeatedly.
In Lead the Endurance, Senior Advisors face this exact decision. The simulation presents a moment where the original plan becomes untenable. Teams that hold on to the original goal waste resources and endanger outcomes. Teams whose leaders can pivot quickly, like Shackleton, preserve their resources for the real priority.
Decision 2: Destroy the Safety Net
After abandoning the crossing, Shackleton ordered the crew to salvage what they could from the Endurance and camp on the ice. When the ship finally sank, the crew lost their shelter, their store of supplies, and their sense of security.
Shackleton could have tried to preserve the ship longer. Instead, he had already moved the crew's mindset away from the ship. He used the ship's destruction as a catalyst. There was no going back. The only option was forward.
The CEO parallel: Organizations maintain legacy products, legacy systems, and legacy structures as safety nets. The old product line that still generates some revenue. The legacy system that nobody wants to depend on and nobody is willing to shut down. The organizational structure that no longer serves the strategy but feels too disruptive to change.
Shackleton understood that safety nets can become anchors. When the option to retreat exists, teams will retreat under pressure. When it does not exist, they commit fully to the new direction.
The Baggage exercise in Lead the Endurance mirrors this principle. Leaders identify the baggage they carry: assumptions, old priorities, comfortable habits that no longer serve them. Naming the baggage is the first step toward letting it go.
Decision 3: Split the Team
The most counterintuitive decision Shackleton made was splitting his crew. He took five men on an 800-mile open-boat journey to South Georgia Island while leaving 22 crew members behind on Elephant Island.
Splitting the team meant trusting other leaders to hold things together in his absence. It meant accepting that he could not control both situations. It meant the crew on Elephant Island had to operate without him for months.
The CEO parallel: Most CEOs struggle to let go of control. They want to be present for every critical decision. They build organizational structures that depend on their involvement. When the organization needs to pursue two critical paths simultaneously, they try to manage both instead of empowering others to lead one.
At ArcelorMittal, 710 leaders went through Lead the Endurance via Duke Corporate Education. The simulation creates moments where leaders must delegate critical decisions to others. Leaders who cannot let go of control become bottlenecks. Leaders who trust their team to execute without them achieve better outcomes.
What All Three Decisions Share
Each decision required Shackleton to give something up:
- His goal (the Antarctic crossing) - His safety net (the ship) - His control (sole leadership of the crew)
These are the three things leaders hold on to most tightly. And they are often the three things that need to be released for the organization to move forward.
Why CEOs Avoid These Decisions
The organizational incentive structure punishes all three decisions. Abandoning a goal looks like failure. Destroying a safety net looks like recklessness. Splitting the team looks like abdication.
Boards reward leaders who hit their stated goals, maintain stable operations, and demonstrate command of their organization. Shackleton-style decisions require a different kind of courage: the willingness to look wrong in the short term to be right in the long term.
The executive development path develops this kind of decision-making courage. Not through lectures about Shackleton. Through practice in simulated environments where these decisions become personal. When a Senior Advisor chooses to abandon the original plan in the simulation, they experience the emotional difficulty of that choice. That experience builds the muscle for real organizational decisions.
The Common Thread
Shackleton's genius was not that he made three bold decisions. It was that he made them quickly, communicated them clearly, and committed to them fully. He did not hedge. He did not revisit. He decided and moved.
Learn2 clients who go through Lead the Endurance consistently report that the Shackleton decisions resonate with their real organizational challenges. The parallel is not historical. It is personal. Every leader in the room recognizes a goal they are holding on to too long, a safety net that has become an anchor, or a need for control that is limiting their organization.
Read leading when the plan fails for more on pivoting under pressure. And see what Shackleton knew about leadership that MBA programs miss for the deeper leadership principles.
Read next: What Shackleton's Hiring Process Teaches About Team Building
[Book a discovery call](https://bookme.name/DougBolger/free-discovery) to explore how the Shackleton leadership principles apply to your organization's current challenges.