Questions for you:
- When did you last deliberately surrender control of your direction — in a project, a conversation, or a physical journey — and what did you notice that you would not otherwise have seen?
- Are there situations in your life where having a destination in mind prevents you from seeing what is actually around you? What would it take to set the destination aside occasionally?
- The walk ended at exactly the right station by chance. How do you distinguish between meaningful coincidence and confirmation bias — seeing the outcome as significant because it happened to fit?
Organisational applications:
The cost of always knowing where you are going: The story’s most direct implication is that goal-directedness, while generally useful, has a specific cost: it filters out everything that does not serve the goal. When the destination is fixed, attention narrows to the route. The Freemasons’ Museum, which the walk took them into, was a building Matt had often passed but never entered. A planned walk from Charing Cross to Euston would not have stopped there.
Organisations that operate exclusively in goal-directed mode — pursuing defined objectives through optimised routes — accumulate the same blind spots. Deliberate departures from the planned path, whether structured like the 90 Waypoint Walk or informal like an unscheduled conversation with someone in a different part of the organisation, are the mechanism by which the things you did not know to look for become visible.
Structured randomness as a tool for attention: The 90 Waypoint Walk is interesting specifically because it is not pure chaos — it has a structure, a set of rules, a finite number of steps. The randomness is bounded and navigable. This is the same principle as the Creativator or Oblique Strategies discussed on other pages – randomness within a structure produces something more useful than either pure randomness or pure structure alone.
For organisations, this suggests that the value is not in abandoning planning but in deliberately building structured departures from it — scheduled time for unstructured exploration, budget for pursuing unexpected leads, permission to follow a thread without knowing where it goes. The 90 waypoints are what make the walk doable; without any structure, it would just be wandering.
The serendipity of arrival: The Euston coincidence at the end of the walk is the story’s most honest moment — Matt notes that the coin toss could have taken them anywhere, but it took Chris home. This is not presented as evidence that random walks always end well, but as an illustration of how unexpected aptness, when it occurs, feels meaningful even though it emerges from a process entirely indifferent to it.
Organisations that cultivate randomised exploration will occasionally produce spectacular coincidences — a customer conversation that reveals an entirely new market, a chance encounter at a conference that resolves an intractable problem. These outcomes cannot be manufactured in advance, but the conditions that make them possible can be deliberately maintained by keeping some navigational control deliberately unexercised.
Further reading
On structured wandering, derived routes, and urban exploration:
The 90 Waypoint Walk — Marcus’s original project page.
The Psychogeography of Cities — the Situationist International concept of the dérive, or unplanned journey through urban environments, is the intellectual antecedent of the 90 Waypoint Walk. Guy Debord’s writings on psychogeography, though not always accessible, cover the idea that surrendering navigational control produces a different and often more revealing relationship with a place.
The Luck Factor by Richard Wiseman. Wiseman’s research on what behavioural habits increase lucky outcomes is directly relevant: people who vary their routines, enter unfamiliar spaces, and are open to unexpected diversions consistently encounter more serendipitous opportunities than those who take the same routes to the same destinations.
On serendipity, attention, and the role of openness:
The Luck Factor by Richard Wiseman. Wiseman’s research on which behavioural habits increase the likelihood of lucky outcomes is directly relevant: people who vary their routines, enter unfamiliar spaces, and are open to unexpected diversions consistently encounter more serendipitous opportunities than those who take the same routes to the same destinations.
Antifragile: Things That Gain from Disorder by Nassim Nicholas Taleb. Taleb’s argument for maintaining optionality — preserving the ability to respond to unexpected opportunities rather than locking all capacity into planned objectives — is the strategic version of not always knowing where you are going.
On exploration, exploitation, and the value of deliberate deviation:
Algorithms to Live By: The Computer Science of Human Decisions by Brian Christian and Tom Griffiths. The chapters on explore/exploit trade-offs are directly relevant: the 90 Waypoint Walk is a deliberate shift into pure exploration mode, and the authors’ account of when exploration produces more value than exploitation provides the formal framework for understanding why this is sometimes the right choice.
The Wisdom of Crowds by James Surowiecki. Surowiecki’s argument for diversity and independence of perspective — the same logic that makes deliberately unplanned routes valuable — is relevant here: an organisation in which everyone follows the same well-worn path accumulates the same blind spots, while one that occasionally sends people in different directions discovers more of the available territory.
Interactive exhibit
A digital incarnation of Marcus’s original walk: https://experiments.randomthebook.com/90waypoint/
About the image
This is the printed map I used when, with a few colleagues, I did the 90-waypoint walk in Farringdon, London, in October 2025. It rained. We did 60 waypoints and bumped into Queen’s guitarist Brian May along the way.
Photo montage and photo by Matt Ballantine, 2026
Random the Book 