Is the best business school cold, wet and moving? Why leadership is often learnt offshore
- Stuart Greenfield

- Jul 29
- 24 min read

Time to change the watch - onboard Morning After off the Hebrides on the 2022 Round Britain and Ireland race.
I went because, at the time, racing boats was a family thing, and seemed a perfectly sensible and exciting way to spend a weekend. The idea that it might turn into a form of education, let alone one with any relevance beyond sailing, did not feature in the plan.
But somewhere in the accumulation of night watches and bad weather, the way you think changes. Not dramatically. Not overnight. But steadily, and with a persistence that is only really noticeable in retrospect. You find yourself less interested in being right in theory and more concerned with getting the decision right in the moment. Less drawn to perfect answers, and more attuned to workable ones. Less comfortable waiting for clarity, and more inclined to act in order to create it.
I should also admit that the sea suits a particular kind of brain: one that craves action, input and attention, all the time. A boat never stops and never stops asking, and for the hyperactive mind that is a gift; the adrenaline does no harm either. Ashore, that restlessness has to be channeled differently. Offshore, it is employed.
“The pessimist complains about the wind; the optimist expects it to change; the realist adjusts the sails.” — attributed to William Arthur Ward
None of this feels particularly significant at the time. It is simply the natural consequence of spending enough hours in situations where the information is incomplete, the conditions are variable, and the outcome depends rather directly on what you choose to do next.
It is only later, usually some time ashore, that you begin to notice that this way of thinking travels rather well.
This article discusses if there is any real evidence or are we just trying to dress up an extreme sport with airs!
I did not set out to develop opinions about leadership. I set out, at an unreasonably young age, to go racing. The opinions arrived uninvited, somewhere between the second reef and the watch change, and over the course of a life time when racing was always second to a business career I still wonder if one helped the other, even if some business ventures were not podium winners!
The case is this: that the offshore racing team, six, eight to twelve people, watches running through the night, decisions delegated and owned at every level of a small and very damp hierarchy, produces a quality of leadership formation that the business world has never fully recognised. The classroom is cold, wet and moving, and the tuition is paid in sleep. It has gone unrecognised largely because the people who have experienced it are too busy either racing or running things to write it down. This is my belated attempt to remedy that, offered with the mild embarrassment of a man who is aware that arguing for the superiority of one’s own hobby is not an entirely objective exercise.
I was reminded of the stakes of this argument on the night of 13 August 1979. I was crew aboard a Sigma 33 in the RORC Fastnet Race, a boat that in the Solent on a summer afternoon felt entirely adequate, and that in the Celtic Sea at midnight in a 45-knot gale felt like rather a bold choice of vessel. We were close to the yachts that were getting into serious trouble that night. The sea was doing things that the forecast had not mentioned and that I have not seen since. We were knocked down: rail under, mast in the water, the particular silence of a boat that has momentarily lost its argument with the ocean. Our skipper turned us around, and we made it safely back to Falmouth. We were lucky.
I was nineteen, a Midshipman in the Royal Navy, and the decision was not mine to make. If I am honest, part of me was probably annoyed to stop racing; nineteen-year-olds usually are. But I watched that decision being made, at close range, and its structure has stayed with me more than most decisions I have made myself in business or otherwise: the incomplete information, the real consequence, the absence of anyone to defer to, the absolute ownership of the outcome. Turning around in those conditions was correct, and the fifteen men who did not come home from that race are the most permanent possible argument for the wisdom of discretion over valour. It is, I have come to understand, exactly the category of decision that the sea specialises in, and that most other environments, including most businesses avoid.
The sea cannot avoid it. The sea, in fact, seems almost designed to produce it, repeatedly, at inconvenient hours, in poor visibility, with a crew that is tired and a forecast that has proved optimistic. This turns out to be, if one survives it in sufficient quantity, a remarkably effective education, perhaps?
“I am not afraid of storms, for I am learning how to sail my ship.” — Louisa May Alcott, Little Women

Ernest Shackleton’s Imperial Trans-Antarctic Expedition of 1914 to 1917
Shackleton: a total failure!
We might as well begin with the greatest offshore manager who, allegedly, ever lived, even though he never, strictly speaking, raced. Ernest Shackleton’s Imperial Trans-Antarctic Expedition of 1914 to 1917 is the foundational text of leadership under pressure, read in business schools from Harvard to INSEAD, and for good reason. But it is rarely read properly as a sailing story. The case-study industry has noticed the survivors. It has never noticed the school that produced them.
Shackleton reportedly placed this advertisement in a London newspaper before the voyage

:
“Men wanted for hazardous journey. Low wages, bitter cold, long hours of complete darkness. Safe return doubtful. Honour and recognition in event of success.” — attributed to Ernest Shackleton, 1914; almost certainly apocryphal, but entirely accurate in spirit
Five thousand men applied . What Shackleton was doing, whether he knew it or not, was the most rigorous pre-selection process in the history of expedition hiring. The advertisement filtered for exactly the attributes that offshore team sailing selects for: appetite for calculated risk, comfort with discomfort, intrinsic rather than extrinsic motivation, and a certain cheerful stubbornness that the Royal Navy once called “press-on-ness” and modern HR departments call “resilience”, a word that has been so thoroughly laundered of meaning that one hesitates to use it.
When Endurance was eventually crushed by pack ice in the Weddell Sea in November 1915, trapped for ten months and slowly stoved in by the remorseless pressure of Antarctic winter, Shackleton did something that most land-based crisis managers fail to do in their first hour: he immediately reframed the objective. The expedition to cross Antarctica was over. The new expedition was to get every man home alive. Every one of the twenty-seven men under his direct command came home.
Shackleton selected his crew with an instinct that any experienced offshore skipper would recognise immediately. He valued the ability to sing, by which he meant something broader than musicianship: the capacity to contribute positively to group morale when the rational course of action would be despair. Frank Wild, his second-in-command, was arguably the finest deputy in polar history: loyal without sycophancy, capable of independent command, never undermining. Every offshore skipper is looking for a Frank Wild. They are, alas, about as common as a Fastnet Race with no wind shifts.
“Difficulties are just things to overcome, after all.” — Ernest Shackleton

when was th eEndurance was eventually crushed by pack ice in the Weddell Sea in November 1915
A scholarly footnote, offered in the spirit of honesty: the Shackleton advertisement has never been found in any newspaper archive. The wording is almost certainly a later invention. It is included here because it accurately distils the documented philosophy of a man whose crew selection diaries and letters reveal exactly the same priorities, and because if Shackleton did not say it, he ought to have.

Depiction of a Royal Navy sea battle in the 18th century
The admiralty school of management
Before Shackleton, and before the RORC had acquired its first rating rule or its first commodore, the sea produced a remarkable generation of leaders whose management challenges make the modern quarterly earnings call look, extremely dull.
Consider Captain James Cook. Three voyages to the Pacific, covering more than 160,000 miles, commanding crews of around a hundred men on vessels that were, by modern standards, barely adequate for a Channel crossing. Cook faced every challenge that a contemporary chief executive faces: resource constraint, personnel management, navigational uncertainty, hostile external stakeholders. But with the addition that the consequences of error were immediate, irreversible, and frequently fatal. The quarterly board meeting has its terrors, but they are of a different order.
Cook's genius was taking the dull jobs seriously. He understood that his greatest enemy was not the reef or the storm but scurvy: the slow organisational rot of poor nutrition, low morale, and systemic neglect. He compelled his crew to eat sauerkraut and fresh provisions at every opportunity, over considerable protest, and did not lose a single man to scurvy. The parallel is not obscure: most organisations are not destroyed by dramatic crises. They are undone by slow, preventable rot that was obvious in retrospect to everyone who was not in charge at the time.
“Ambition leads me not only farther than any other man has been before me, but as far as I think it is possible for man to go.” — Captain James Cook
Lord Nelson is a more operationally ambiguous study, but a crucial one. Nelson was not merely brave; he was a systems thinker. His famous “Nelson Touch”, the breaking of the Franco-Spanish line at Trafalgar, was the product of extensive briefing of his captains, a pre-agreed doctrine, and a culture of initiative that he had spent years cultivating. He told his officers that no captain could do very wrong who placed his ship alongside that of an enemy. This is not recklessness; it is the delegation of decision-making to the lowest competent level, combined with a crystal-clear statement of intent. Silicon Valley would call it “commander’s intent”. Nelson simply called it common sense, which may explain why Silicon Valley needs to reinvent it.
The offshore racing world has its own version of this culture. When you round a racing mark at midnight in building sea state and increasing wind with a crew who are cold, tired, and making small errors, you cannot manage every decision from the helm. The crew must understand the intent, have the skill, and possess the confidence to act. The skipper’s job at that moment is not to control but to trust, and to have built that trust through the accumulated evidence of every watch, every debrief, and every difficult conversation that came before.
The watch system: the organisational model the boardroom never borrowed
Here is an argument that offshore sailors rarely make explicitly, perhaps because it feels so obvious to those who have lived it that saying it aloud seems patronising. It should not. It is the strongest single argument for the leadership value of team offshore racing, and it is almost entirely invisible to anyone who has not done it.
The offshore watch system is the most sophisticated model of distributed accountability in sport. Every three or four hours, one group of human beings formally hands the management of a complex, moving, potentially dangerous asset to another group, in conditions that range from the merely uncomfortable to the actively alarming. The handover is not a formality. It is a discipline, one that the Royal Navy has been practising for centuries and that business organisations, for reasons that presumably made sense at the time, have never quite adopted.
The incoming watch arrives on deck ten minutes early, already dressed, already fed, acclimatised to the conditions before they assume responsibility. The outgoing watch leader briefs the incoming one: the tactical situation, the sail configuration, the weather trend, any vessels nearby, the agreed parameters for waking the skipper, any developing mechanical concerns. These are not conversational suggestions. They are the formal transfer of ownership. From the moment the handover is complete, the incoming watch owns every decision made on their watch. There is no “that was the other watch’s call”. There is no blame transfer, no renegotiation of prior decisions in deteriorating conditions, no abdication dressed up as consultation.
“When there’s no communication through the boat, and maybe a lack of trust, you get in situations when the crew suddenly decide they’re going to call the gybe because the navigator’s asleep and you don’t want to disturb him. With the seasoned pros, this lack of communication is never allowed to happen.” — Pete Cumming, watch captain, 100ft Maxi Scallywag , in Yachting World
What this teaches, repeated across dozens of races and hundreds of watch changes, is that accountability is not a punishment but a system. That the documentation of state, where we are, what we know, what we don’t know, what needs watching, is not bureaucracy but operational necessity. That the person coming on shift inherits not just the task but the reasoning behind the decisions already made, and that the quality of the handover determines the quality of everything that follows.
Most businesses have shift handovers of a kind. Almost none have them with the rigour of an offshore racing yacht, because almost none have the immediate consequence structure that makes rigour feel necessary rather than optional. The factory floor shift change, the hospital nursing handover, the nuclear power station control room transfer: these are the land-based equivalents, and it is worth noting that these are also the contexts where organisational failures are most catastrophic and most systematically studied.
The watch leader, that figure below skipper, above ordinary crew, responsible for the boat and every decision made on it during their watch, is the middle management position that offshore racing has perfected and that business schools have yet to adequately theorise. They must motivate without full authority, decide without the safety net of a superior on deck, and maintain standards in precisely the conditions when the temptation to let things slide is greatest. These are the conditions that reveal character. They are also the conditions that form it.
1979: The race that became a management inquiry

The Royal Navy airlifted 74 survivors during three days of rescues
To understand what offshore racing teaches about institutional learning, the capacity of an organisation to absorb catastrophe, examine itself without flinching, and emerge with improved systems, one must understand 1979. Not because it is a comfortable story. It is not. But because the response to it is.
The Fastnet Race of August 1979 was the twenty-eighth running of the event, and the climax of that year’s Admiral’s Cup, effectively the world championship of offshore racing. Three hundred and three yachts started from Cowes on 11 August. The shipping forecast at 1355 on the 13th offered nothing alarming: south-westerly force four to six, increasing six or seven for a time. By midnight, the fleet was in conditions that no forecast had predicted and that no competitor had encountered before.
A deepening Atlantic low intensified faster than any meteorological model of the era could track. Winds reached sixty knots. Wave heights touched forty feet, with confused cross-seas generating breaking crests of extraordinary violence. Of the 303 starters, only 86 finished. At least 75 boats were knocked down beyond horizontal; some rolled through a full 360 degrees. Five sank. Twenty-four were abandoned. Fifteen competitors died, and six more people were lost from boats following the race. It remains the deadliest offshore race in history.
“It was a soul-chilling surge of fear as we heard the terrifying sound of a breaking wave forty feet above us.” — survivor account, quoted in the official Fastnet Race Inquiry
The response of the Royal Yachting Association and the RORC was, in the context of how sporting organisations typically respond to catastrophe, quietly exceptional. They commissioned an immediate joint inquiry, distributed questionnaires to the skipper and crew of every yacht, and fed the completed responses into a computer for analysis: a remarkable piece of data collection for 1979. The inquiry examined weather reporting, safety gear, crew experience, hull design, stability, life raft performance, and rescue procedures with a thoroughness that would not disgrace a modern accident investigation board.
The findings were uncomfortable, because they implicated not just the weather but the rule. The International Offshore Rule, which governed the design of most racing yachts at the time, had produced a generation of boats with light displacement, and critically low angles of vanishing stability, some as low as 90 degrees, meaning a boat heeled past that point would invert and stay inverted. Several did. The IOR had been distorting yacht design for a decade in pursuit of rating advantage, and the 1979 Fastnet was, in the bluntest possible terms, the result.
The consequences were systemic and lasting. Crew qualification requirements were introduced. Mandatory VHF radio, stronger harness standards, revised stability requirements, redesigned companionways, the instruction never to abandon a yacht until it is actually sinking (many of the boats abandoned in 1979 were later found floating, crewless): all trace directly to the inquiry’s recommendations. The Offshore Special Regulations that govern serious ocean racing today are built on the foundations of what the RORC and RYA learned from 1979.
This is the offshore racing community at its institutional best: honest self-examination, systematic learning, and the willingness to impose uncomfortable reforms on a constituency that included some of the most powerful and opinionated people in British sport. It is not a bad model for any organisation that has suffered a serious failure and is deciding what to do next.
The rating rule as management parable
The history of offshore rating rules is, for those who have followed it closely, one of the more instructive comedies in competitive sport, and a near-perfect allegory for the dynamics of competitive markets, regulatory ingenuity, and the inevitable gap between what rule-makers intend and what rule-exploiters achieve.
The International Offshore Rule, adopted in 1970 as a merger of the American CCA rule and the RORC’s own system, was an attempt to do something truly ambitious: to create a single, internationally accepted framework within which any yacht, of any size and type, could race fairly against any other. The formula was complex, the ambition admirable, and the execution, as the technical literature now makes abundantly clear, progressively catastrophic.
Designers, as designers will, immediately began finding the gaps. The IOR estimated displacement from hull measurements rather than actually weighing the boat, and measured length using girth stations that could be distorted between the measurement points without affecting the rating. The result was a generation of boats with perceptible bumps and hollows in their hull profiles: local distortions inserted purely to persuade the rule that the boat was a different shape from the one it actually sailed. The tea-kettle hull became notorious: wide amidships, pinched at the ends, with a stability range that was acceptable in a marina and alarming in a gale. As was demonstrated, at some cost, in 1979.
“A subject never to be fully settled.” — Nathanael G. Herreshoff, on rating rules, with rather more prescience than anyone appreciated at the time
The IOR died in the early 1990s, finally undone by a combination of the 1979 Fastnet’s implicit indictment of the boats it had produced, an eye-wateringly expensive design arms race at the top of the fleet, and the simple fact that it had changed so often, in response to so many exploits, that the owner base had lost all confidence in its stability. The Channel Handicap System, born in 1983 from a conversation in Paris between the RORC Commodore and his French counterpart Jean-Louis Fabry of the UNCL, and famously summarised on the back of an envelope, together with its descendant IRC, has proved considerably more durable, precisely because it prioritises stability and breadth of participation over technical precision.
Every regulatory framework faces exactly this version of the problem: the rules are written by people of good intent who cannot anticipate every application of competitive ingenuity, and the most motivated participants will find the loopholes before the rule-makers know the loopholes exist. The offshore racing community has lived this cycle repeatedly, learned from it, and, with IRC, arrived at something that works. It is a model that financial regulators might study with modest profit, and significantly less drama.
The Royal Ocean Racing Club and its huge influence
The Royal Ocean Racing Club was founded in 1925, by men who,amongst other things, may have believed that offshore racing produced better sailors and, by extension, better people. The first Fastnet Race had been sailed the same year and was the catalyst for the founding of the club.
The RORC’s early Commodores and Chairmen were, almost without exception, people of considerable achievement ashore. This was not a coincidence of class, though the RORC’s early culture was not without its social issues, but something more fundamental. Offshore sailing is difficult in ways that are not easily simulated, and real difficulty remains the only reliable teacher. The men who built the RORC understood this, even if they would not have described it in those terms.
The club’s great service to the sport was not the racing itself but the institutional framework it built around the racing: the rating rules, the safety regulations, the qualification requirements, the Offshore Special Regulations that eventually became the global standard. None of this happened by accident, and none of it happened without argument. The RORC is, among its other distinctions, an organisation that has been arguing productively about the right way to do things for a hundred years, which puts it ahead of most.
“The sea finds out everything you did wrong.” — Francis Stokes, single-handed transatlantic veteran, who spent considerable time finding this out personally, and kept going regardless
Women who changed the race: What Maiden taught us about leadership

The offshore racing world has not always been a comfortable place for women. This is not a secret, and the sport’s slow candour about its own history is, in retrospect, one of its more admirable qualities. The story of Tracy Edwards and Maiden belongs at the centre of any serious argument about what offshore team racing teaches, not because it is an exceptional story, though it is, but because it demonstrates the thesis under the kind of pressure that makes the thesis either prove itself or collapse.
In 1985, Tracy Edwards was working as cook on the Whitbread Round the World Race and noticed that of 230 crew in the entire fleet, exactly four were women. The response of the men around her was not, in most cases, mere indifference. When she subsequently asked to race rather than cook, the response from one skipper was direct enough to quote in polite company only in paraphrase, and sufficiently motivating to last her a career.
Her solution was characteristically offshore in its logic: if the existing teams will not have you, build your own. She found a 58-foot Bruce Farr-designed yacht in poor condition, named her Maiden , and restored her with a crew that painted the hull, installed the rig, ran the electrics, plumbed the heads, and wired the navigation station themselves. Edwards later observed that by the time Maiden went into the water for the 1989 Whitbread, her crew knew their boat better than any other team in the race. This is not a decorative detail. It is the central point.
“If you don’t like the way the world looks, change it.” — Pat Edwards, Tracy’s mother, and, as it turned out, the founding philosophy of the Maiden campaign
The yachting journalist Bob Fisher famously described Maiden as “a tin full of tarts”, a line that proved, if nothing else, that motivational techniques come in unexpected forms. Maiden won two of the six legs in her class and finished second in class overall, the best result for a British boat in seventeen years. Tracy Edwards became the first woman to win the Yachtsman of the Year Trophy. Business schools eventually caught up too: a two-part case study on the campaign’s management challenges is now taught through Harvard Business Publishing, which rather suggests that the management academics got there in the end, even if the yachting press took longer.
Grant Dalton, a Whitbread rival of Maiden’s era and now CEO of Emirates Team New Zealand, would later supply the sport’s definitive hostage to fortune: before the 2001–02 Volvo Ocean Race he declared that if Lisa McDonald’s all-female crew on Amer Sports Too beat his boat, he would walk up Queen Street in Auckland with a pineapple positioned where no pineapple should be. They did not. One feels the sport was denied something memorable.
The sport’s evolution on gender has been slow and occasionally undignified, but it has been real. The Ocean Race now mandates mixed crews. Pip Hare’s Vendée Globe campaigns have been run with a professional sophistication that reflects well on the sport and not at all badly on the argument being made here. The direction of travel is clear, even if the pace has left something to be desired.

Was it the management that helped Australia win the America’s Cup?
The America’s Cup and the management of excellence
No account of offshore racing’s relationship with leadership would be complete without the America’s Cup: the oldest international sporting trophy, first competed for in 1851, and for 170 years a laboratory for the intersection of technology, money, competitive strategy, and the particular kind of controlled obsession that produces both great campaigns and interesting therapy bills.
The 1983 Cup, the first time the trophy left American hands, won by Australia II and her revolutionary winged keel, is the most instructive episode in the series. The Australians won not because they had more resource but because they had a better idea and the management discipline to protect it. The Bond syndicate’s operational security around the keel design was, in an era before industrial espionage was a formal competitive concern, extraordinary. By the time the New York Yacht Club’s challenges to the keel’s legality had run their course, it was too late for Newport to respond. The lesson is not about the keel. It is about information as a strategic asset and the discipline required to manage it.
The American Twelve-Metre programme at Newport that summer was a study in the gap between resource and performance. The New York Yacht Club had every advantage except the right one: a willingness to question its own assumptions. Liberty was a fine boat by conventional standards. Australia II was not a conventional boat. The NYYC had held the Cup for 132 years and had, perhaps understandably, developed certain views about how Twelve-Metres were meant to look.

Dennis Conner, who lost the Cup in 1983 and won it back in Fremantle in 1987 with Stars & Stripes
Dennis Conner, who lost the Cup in 1983 and won it back in Fremantle in 1987 with Stars & Stripes , is the offshore racing world’s most compelling study in managerial recovery. His Stars & Stripes campaign was built on systematic preparation: comprehensive weather analysis of the Fremantle Doctor, hulls designed and tested specifically for those conditions, a training programme of uncommon discipline. He was not likeable in the manner of a modern brand ambassador. He was effective in the manner of someone who had understood, at some personal cost, that effectiveness was the point.

The Whitbread, the Volvo, and the Ocean Race: managing the long game
If the Fastnet Race is the examination, the Whitbread Round the World Race, now the Ocean Race, having passed through the Volvo years with its reputation enhanced and its format refined, is the doctoral thesis. Months at sea, thousands of miles, multiple legs, multiple crew rotations, multiple cultures, and the sustained management challenge of keeping a programme coherent across an entire circumnavigation. The final examination is not held in a building. It is held somewhere south of the roaring forties, at three in the morning, in conditions that were not in the brief.
Robin Knox-Johnston, who had already, in 1968 to 1969, become the first person to sail solo non-stop around the world in his small wooden ketch Suhaili , brought to the Whitbread a quality that distinguished him from almost every other competitor: the absolute refusal to complain. His log of the solo circumnavigation is a masterclass in operational stoicism. When things went wrong, and they went wrong regularly, he fixed them, noted them, and moved on. There is no self-pity in the record. This quality is rarer than it sounds, and considerably more useful than it looks.
Peter Blake, who dominated the Whitbread in the 1990s and then broke the Jules Verne Trophy record before his murder in the Amazon in 2001, was a different kind of leader: more expansive, more charismatic, with a particular genius for the cultivation of team identity. The red socks that became the symbol of his 1995 America’s Cup campaign, and eventually of Team New Zealand itself, were not a marketing exercise. They were a tribal marker, a daily reminder that the crew belonged to something specific and shared. Modern sports psychologists would write papers about it. Blake simply understood that people perform best when they belong to something larger than themselves.
“You must be driven by a dream, and you have to make sacrifices.” — Sir Peter Blake

Vestas - Ended up on a reef - too much tech, not enough old school management perhaps,. No life was lost fortunately but some serious lessons learnt
The Volvo Ocean Race era introduced professional management structures to what had been a sport of gifted amateurs and inspired enthusiasts. Data-driven, systems-oriented, with weather routing, structured watch systems, and performance analytics that would have baffled anyone who raced in the 1960s. This is not worse, merely different. And it raises a question that the offshore racing world continues to wrestle with, as does every organisation that grows beyond its founding culture: whether the systems serve the people, or the people serve the systems.
The singular case of the single-handers, and why this is not about them. Well, maybe a bit.

Francis Chichester’s solo circumnavigation in Gipsy Moth IV , completed in 1966 to 1967
The single-hander must now be addressed directly, and without the diplomatic vagueness that the offshore community sometimes extends to its most celebrated members. The Vendée Globe is a magnificent human achievement. It is also, from the perspective of the argument being made here, something of a magnificent distraction.
The solo offshore sailor is not simply an offshore sailor with a reduced crew. They are a different organism entirely, with a different relationship to risk, decision-making, and the management of self. Francis Chichester’s solo circumnavigation in Gipsy Moth IV , completed in 1966 to 1967 at the age of 65, nearly lost south of New Zealand, and completed anyway, is a study in individual project management and the management of fear that would not disgrace any business biography. His knighthood was ceremonially conferred at Greenwich with the same sword used to knight Francis Drake. One feels the Queen grasped exactly what she was honouring.
But Chichester’s qualities, meticulous preparation, obsessive self-reliance, a perfectionist’s relationship with his vessel, are different in kind from what the team offshore race produces. The solo sailor cannot distribute trust, because there is no one to trust. They cannot delegate, because there is no one available. They cannot run a watch system, conduct a handover, or develop the collaborative instincts that organisations actually require. What they develop instead is something extraordinary but qualitatively distinct: a refined, almost brutal capacity for self-reliance, and a decision-making loop that admits no external input.
There is a word for this quality applied to organisational leadership: autocracy. It has its moments, usually in real crises of short duration, but as a permanent management style it is limiting. The finest solo offshore sailors seem to understand this intuitively. Ellen MacArthur, who retired from racing at thirty-two and became one of the most effective environmental advocates of her generation through the Ellen MacArthur Foundation’s circular economy work, transferred her qualities not into autocratic leadership but into systems thinking. When you sail alone around the world, you learn that you are entirely dependent on your preparation, your protocols, and your equipment. You cannot call for help. You must have thought of everything in advance. This turns out to be superb training for designing systems. It is less reliable training for leading people through problems nobody anticipated.
Blondie Hasler, the Royal Marine officer who adapted the Chinese junk rig for ocean sailing, pioneered wind-vane self-steering, and drove the creation of the Observer Single-handed Transatlantic Race, understood this distinction with characteristic English obliqueness. The OSTAR, first run in 1960, was Hasler’s answer to a question nobody else had thought to ask: what happens when you remove the social scaffolding of crew entirely? The answer, as sixty years of solo racing has demonstrated, is that you find out exactly who the sailor is. This is valuable. It is not, by itself, leadership formation.
“The solo racing world is for those for whom the boat is the relationship. The team offshore world is for those for whom the crew is the boat.” — an aphorism earned rather than invented
None of this diminishes the achievement of the Vendée Globe finishers or the OSTAR veterans. It is simply to say that the qualities they develop, extraordinary individual resilience, supreme self-sufficiency, a high tolerance for productive solitude, are different from, and in some respects in tension with, what offshore team racing develops. Both are valuable. They are not interchangeable.
The counter-argument. Being honest, I’m making it look good.
The counter-argument is straightforward enough: plenty of exceptional leaders have never been near an offshore yacht, and a fair number of thoroughly mediocre ones have done many Fastnets. Warren Buffett has not, to anyone’s knowledge, rounded the Rock. There are distinguished RORC alumni who have made a complete mess of their businesses, and distinguished business leaders who have never sailed a night watch in their lives and show no signs of being worse for it.
All true. The response is equally plain: the thesis is not that offshore sailing guarantees good leaders, or that it is sufficient on its own, or that it is the only route. The thesis is more modest and, one hopes, more defensible: that offshore team sailing selects for and develops, at a concentration and intensity that most other available experiences do not match, a specific cluster of attributes that leadership requires. Decision-making under irreducible uncertainty. Accountability without blame transfer. The management of fatigued, cold, skilled, opinionated people towards a shared objective in conditions that no one planned for. The capacity to remain functionally rational when the emotional case for panic is at its most persuasive.
These attributes are not common. They are not reliably produced by case studies, simulations, or management retreats, however well designed. The sea is a better teacher not because it is harsher but because it is more honest: the feedback is immediate, unmediated, and impossible to argue with. A boat that has been sailed badly does not issue a memo. It heels too far and loses speed, or it loses its rig, or it takes on water. The connection between decision and consequence is as short as it gets outside a real operational crisis.
The thesis is probabilistic rather than deterministic: all else being equal, the person who has done serious offshore team racing is more likely to have the attributes in question than the person who has not. The “all else being equal” is doing some work in that sentence, as it always does. But it is doing less work than the sceptic supposes.
So what is the future for crewed offshore racing?
There is a question that the offshore racing community has not yet answered adequately, and it is the question on which this essay’s argument ultimately depends. Not whether offshore team racing produces the qualities described; the evidence for that seems reasonably compelling. But whether the conditions under which it does so are being maintained.
The professionalisation of the Ocean Race has replaced the gifted amateur with the technical specialist. The people sailing the fastest boats in offshore racing today are overwhelmingly professional sailors for whom the boat is a workplace and the race a contract deliverable. They are, without question, more technically capable than any previous generation. They are also, for the most part, not the future managing directors, entrepreneurs, and institutional leaders that earlier generations of offshore racing produced. The professional offshore sailor is an outstanding professional in his or her own niche. That is a different thing.
The RORC IRC fleet, the several hundred boats racing across the Channel through the summer, the biennial Fastnet, the annual Caribbean 600, and their sister events under the IRC rule, is where the formation still happens. This is the world of the owner-driver, the semi-professional crew in a largely amateur programme, the corporate team whose Fastnet entry turns out to be rather more demanding than the team-building exercises they have done before. It is also, increasingly, a world that is economically difficult to enter. A competitive IRC offshore campaign is not cheap, and the barrier to entry has risen steadily without a corresponding expansion in the pool of people able to clear it.
This is the strongest practical argument for the active expansion of team offshore racing. Not the professional circuit, which is doing perfectly well on its own terms, but the amateur and semi-professional tier where the formation actually occurs. Reducing the cost of competitive offshore participation, building accessible pathways from club racing to offshore campaigns, creating sponsorship structures that bring new people into the fleet rather than simply rebranding existing ones: these are investments in something considerably larger than sport. They are investments in the leadership pipeline of the next generation, made in the one environment that has been reliably producing that pipeline for a hundred years.
The sea has been producing leaders for as long as there have been ships. The question is whether we are paying enough attention to keep it doing so. The best business school is cold, wet and moving. Term starts on Saturday, off Cowes.




Comments