A Story About Dilemmas

A Glaswegian woman, a child of World War II, grew up knowing two things for certain about the life she wanted: a highly adventurous world-traveling life and children. For most people, these two desires would be in perpetual conflict. For her, they were as inseparable as two sides of the same coin.

Her adventures would eventually take her to nearly 100 countries, and she would bring her children to most of them. She took her first child, by boat, halfway around the globe when he was just a month old, completing the circumnavigation five years later with another child in tow. She travelled long stretches of the world’s three longest rivers and through pirate-infested waters off the coast of Somalia. She drove from Scotland to Yemen, and twice from Scotland to Jordan and back again, the first time with her two-, three-, and seven-year-old children. They passed through Syria during a civil war. They navigated the Empty Quarter of the Arabian Peninsula. They drove deep into the Hejaz region of Saudi Arabia to visit a sixth-century Christian monastery and to see rare petroglyphs in Qilwah; No roads, just maps and a compass.

This was the texture of her life: extraordinary, deliberate, and carrying genuine risk. The thread running through it all was a tension she never fully resolved. She wanted adventures for herself and her children. But how do you have those adventures while keeping your children safe? This was her lifelong dilemma. There had to be trade-offs. There had to be detailed plans and contingencies. There had to be courage because it was never entirely safe, but it was never boring.

Her willingness to navigate that tension, rather than resolving it by choosing either adventure or kids, produced moments of formation that no school or suburban childhood could replicate.

For example, when her oldest son was 14, to help him expand his horizons and improve his French, his mother checked him into a Paris youth hostel. She gave him a map of the city, a list of places to visit, sufficient cash, a train ticket to London, and the address of a friend’s house in the north of England to meet at in five days. The hostel was home to global nomads and a colourful cast of misfits from six continents, with wanderlust similar to the boys’ family. He explored the Catacombs, Versailles, and the Louvre, located the graves of Oscar Wilde and Jim Morrison, and climbed the Eiffel Tower, all items from his mother’s list. He also went ‘off-piste’ for his own adventures, such as navigating the Pigalle neighbourhood on a Saturday night, and knocking on the side door of a patisserie at 5:00 a.m. for fresh croissants.

Somehow, he made his train at Gare du Nord, arriving in London on a Sunday afternoon with no money, and so stood on the street asking strangers for the money for a train ticket to Carlisle. He finally arrived at the friends’ door that evening, having done and seen a few things not entirely ideal for a fourteen-year-old, but having had a life-enhancing experience. It led in no small part to his decision, twenty-six years later, to return to Paris to study, where he met his future business partners and formed friendships that would shape the rest of his life.

The mother told her son that leaving him alone in another country had been both one of the easiest and hardest decisions she had ever made, and that it led to one of the most anxious weeks of her life. She had no doubt he could manage on his own, but she could not sleep properly until he knocked on that door 5 days later.

She never resolved the tension between adventure and safety. She managed it. Every trip was a negotiation between those two values. Every decision was a trade-off. What she modelled, without knowing it, was the art of living with a genuine dilemma.

In every time of profound turbulence, whether driven by war, technological disruption, or political upheaval, leaders face a recurring trap. We may reach for the tools that served us well in calmer times: analytical frameworks, best practices, decisive action plans. These are the tools of problem-solving. But the defining challenges of volatile periods are rarely problems. They are dilemmas. And that distinction, misunderstood or ignored, is the root cause of many leadership failures.

This article explores the fundamental difference between problems and dilemmas, examines how this distinction plays out in two of the most pressing situations facing governments and corporations today, and offers four approaches that leaders can use to navigate genuine uncertainty without relying on the false comfort of premature resolution.

The Core Distinction: Problems vs. Dilemmas

The terms “problem” and “dilemma” are often used interchangeably. This conflation is not merely semantic; it is operationally dangerous.

Problems Are Solvable

A problem, in the strict leadership sense, is a situation with a discoverable answer. It may be complex, resource-intensive, and time-consuming, but it has a solution. A supply chain bottleneck is a problem. A product defect is a problem. A cash flow gap is a problem. These situations call for analysis, expertise, and execution.

Problems respond to “technical work”, applying existing knowledge and established methods to a challenge that is reasonably well understood.[1] Harvard professor Ronald Heifetz, who coined the term ‘adaptive leadership’, distinguishes between technical problems, for which authoritative expertise can supply a known solution, and adaptive challenges, which require innovation and changes in values, beliefs, or behaviour.[2]

Dilemmas Are Irreducible Tensions

A dilemma, by contrast, involves two or more values, goals, or imperatives in genuine tension, where advancing one necessarily constrains the other, and where no analytical solution fully resolves the conflict. Dilemmas do not have answers. They have trade-offs. They require not the mindset of the engineer but the judgment of the experienced diplomat.

Exceptional leaders can hold two opposing ideas in constructive tension and generate creative resolutions superior to either alternative in isolation, using what Roger Martin, in The Opposable Mind (2007), calls “integrative thinking.” [3] A government deciding whether to impose costs on its own economy to advance strategic interests is a dilemma. A corporation navigating between productivity gains and obligations to its people is a dilemma. These are genuine value conflicts, not information gaps.

While navigating dilemmas, you still must solve problems, but they always serve the tensions in play. For example, in the story of the mother, while planning the Saudi desert journey, deciding who should make the trip was a problem to embrace, in the service of the dilemma. She wanted four vehicles for the trip so no one would have to travel alone in an emergency. She wanted vehicle ‘interoperability’ so that they could share spare parts and tires if needed. She chose an archaeologist for his expertise. Critically, she chose someone she suspected was an MI6 officer, reasoning that if anything went wrong during the excursion, the UK government would find him and bring him home, thereby increasing the safety of the entire group, and specifically, her family. It later turned out she was correct in her suspicion.

“The most dangerous leadership error is treating a dilemma as if it were a problem, because it leads to false certainty, premature closure, and decisions that unravel under pressure.”

Why the Confusion Is So Costly

The instinct to convert dilemmas into problems is deeply human. Ambiguity is psychologically uncomfortable, particularly for leaders who are expected to project confidence. But forcing a dilemma into the frame of a problem produces failure: strategies that optimize one value at the cost of another, coalitions that fracture when trade-offs become visible, and crises that recur because the underlying tension was suppressed rather than navigated.

Conversely, treating a genuine problem as a dilemma, overthinking it, seeking endless consultation, and delaying action wastes time and erodes trust. We have all seen leaders who cannot distinguish between the two, leaving them perpetually overconfident or paralyzed. Both are fatal in times of great change.

Case Study I: The Strait of Hormuz and the Dilemma of Strategic Dependency

No geopolitical situation better illustrates the problem-dilemma distinction in 2026 than the crisis unfolding in and around the Strait of Hormuz. What is often framed as a security or logistics problem is, for most national governments, a profound structural dilemma, and leaders who have treated it as the former have found themselves acutely unprepared for the latter.

It is instructional to listen carefully to how the media and leaders describe the news from the Persian Gulf at present. Watch carefully for questions and answers that are problem-centric, not dilemma-centric.

The Strategic Stakes

The Strait of Hormuz is the world’s most critical energy chokepoint. At its narrowest, it measures just 33 kilometres across, with shipping lanes barely three kilometres wide in either direction.[4] According to the U.S. Energy Information Administration, approximately 20 million barrels of oil transit the Strait daily, roughly 20 percent of global oil supply, and about 20% of global liquid natural gas (LNG) too. Critically, around 80 percent of that oil is destined for Asia: China, India, Japan, and South Korea combined account for nearly 70 percent of all crude passing through the strait.

The February-March 2026 conflict between the United States, Israel, and Iran has, at the time of writing, transformed a long-standing risk into an active, ongoing disruption. Following joint U.S.-Israeli airstrikes on Iran beginning on 28 February 2026, Iran’s Islamic Revolutionary Guard Corps (IRGC) declared the strait “closed” and began attacking vessels attempting to transit. Tanker traffic dropped by approximately 70 percent before falling to near zero. Oil prices, which stood at roughly $65 per barrel before hostilities commenced, broke the $100 mark within days. War-risk ship insurance premiums increased by four to six times within a single week.

The Dilemma Governments Face

For the governments most exposed to the crisis, Japan, South Korea, India, China, and the European states dependent on Gulf LNG, the Strait of Hormuz situation is not a problem awaiting a technical solution. It is a structural dilemma between two legitimate imperatives: energy security and geopolitical alignment.

Iran’s clearly planned response has been deliberately differentiated. Rather than closing the Strait universally, Tehran has signalled its willingness to grant safe passage to vessels from states not aligned with U.S.-Israeli operations, a move designed precisely to exploit the dilemma of non-aligned governments. Pakistan-flagged tankers received passage. India was granted exceptions for two LNG carriers bound for western Indian ports. Turkey secured passage for a vessel after direct diplomatic engagement. China entered negotiations to protect both crude oil flows and Qatari LNG shipments. The Malaysian Prime Minister announced on 26th March 2026 that they had “spoken to the leaders of Iran, Egypt, Turkey, and other regional leaders” and that Malaysian vessels were now being allowed to pass through the Strait of Hormuz. These exceptions were not offered on the basis of legal right; they were exchanges based on geopolitical positioning.

For Japan and South Korea, the dilemma is particularly acute. Deep alliance obligations to the United States pull in one direction. Energy security, the literal functioning of their industrial economies, pulls in another. Neither imperative can be fully satisfied without compromising the other.

For governments that had treated their energy dependency as a supply chain problem to be optimized, rather than a strategic dilemma to be managed, this moment has arrived without adequate preparation. The leaders now navigating it most effectively are those who recognized, years earlier, that dependency on a single chokepoint created not a logistical challenge but an ongoing geopolitical exposure requiring sustained, deliberate management.

The Business Downstream

For corporations, the Hormuz crisis is a downstream consequence of a failure to recognize dilemmas at the governmental level, and a stark warning to any executive who has treated geopolitical exposure as a risk to be monitored rather than a dilemma to be navigated. Companies with supply chains running through Gulf energy have found themselves at the mercy of decisions made by governments that were themselves unprepared.

The Hormuz situation is, at its core, a dilemma between two values that cannot be simultaneously maximised: the efficiency of concentrated, optimised global supply chains and the resilience of distributed, redundant alternatives. Leaders who built for efficiency found themselves exposed. Leaders who had built in resilience, at some cost to efficiency, found themselves better positioned to absorb the shock.