Questions for you:
- Are you generally a walker or a rider? Do you tend to prefer a certain but imperfect outcome, or are you willing to accept a worse downside for a shot at the better one?
- How aware are you of your own risk tolerance when making decisions at work, and how much does that vary depending on what you stand to lose personally rather than professionally?
- Can you think of a decision you made recently that was shaped more by how much you hated a possible outcome than by a clear-eyed assessment of the probabilities involved?
Organisational applications:
Making risk tolerance explicit in decision-making processes: The bus dilemma makes visible something that most organisational decisions leave implicit: the choice between a certain modest loss and an uncertain outcome with a larger potential downside is not resolved by probability alone. It depends on how much the decision-maker weighs regret, how consequential the downside is given their current circumstances, and how much variance they can absorb.
In organisational settings, these factors vary considerably across individuals, roles, and departments, yet they are rarely surfaced in decision processes. A finance team and a product team presented with the same risk profile will often reach different conclusions for reasons unrelated to the data. Making risk tolerance an explicit part of how decisions are framed, rather than assuming it is shared, tends to produce better-calibrated outcomes and fewer post-decision recriminations.
The asymmetry between walkers and riders in organisational culture: Most organisations have an implicit default, either towards caution, preferring a certain outcome, or towards opportunity-seeking, preferring the best. This default is rarely articulated and often inconsistent, varying by seniority, function, and recent organisational history.
Teams that have recently experienced a high-profile failure tend to shift towards the equivalent of walking in this analogy, regardless of whether the specific circumstances warrant it. Teams in growth phases tend to “ride” regardless of the actual odds. Neither tendency is inherently wrong, but both can produce systematic errors: persistent “walking” means foregone upside in high-opportunity environments, and persistent “riding” means unnecessary exposure in low-margin ones. Periodically examining which default is in effect and whether it is appropriate to current conditions is more useful than debating individual decisions.
Regret as an underacknowledged variable in organisational risk assessment: Standard risk frameworks assess the probability and magnitude of outcomes. They rarely capture regret asymmetry, the well-documented tendency for people to feel losses more acutely than equivalent gains, and to weigh anticipated regret disproportionately in decisions. In the bus dilemma this shows up as the particular aversion to being later than if you had walked: the same lateness feels worse when it results from an active choice to wait than when it results from simply having started walking.
Organisations exhibit the same pattern. A decision that produces a bad outcome is judged more harshly when it involves an active choice to take a risk than when it involves passive continuation of the status quo, even when the probability and magnitude were identical. Being aware of this bias does not eliminate it, but it can prevent risk assessments from being systematically skewed towards inaction.
Further reading
On decision-making under uncertainty and expected utility:
Struck by Lightning: The Curious World of Probabilities by Jeffrey Rosenthal. The source of the walk-or-ride dilemma itself. Rosenthal’s broader account of everyday probability is accessible and directly relevant to the story’s approach of finding decision theory in mundane situations.
Against the Gods: The Remarkable Story of Risk by Peter L. Bernstein. Covers the development of expected utility theory from Bernoulli onwards, providing historical context for why the bus dilemma is not a trivial puzzle but a compressed version of one of the central problems in the mathematics of decision-making.
On risk tolerance, loss aversion, and regret:
Thinking, Fast and Slow by Daniel Kahneman. Kahneman’s treatment of prospect theory and loss aversion is the most thorough account of why the certain-but-modest-loss option consistently feels more attractive than probability calculations alone would predict.
Thinking in Bets: Making Smarter Decisions When You Don’t Have All the Facts by Annie Duke. Duke’s framework for separating decision quality from outcome quality is useful for organisations that tend to judge past risk decisions by their outcomes rather than by whether they were reasonable given what was known at the time.
On satisficing, optimising, and decision thresholds:
The Paradox of Choice: Why More is Less by Barry Schwartz. Schwartz’s account of the psychological costs of optimising in uncertain environments connects directly to the story’s observation that neither walkers nor riders are categorically right, and that the drive to find the best option in genuinely uncertain conditions tends to produce worse outcomes than setting a threshold and committing to it.
Algorithms to Live By: The Computer Science of Human Decisions by Brian Christian and Tom Griffiths. The chapter on optimal stopping, covering the secretary problem and related decision puzzles, provides the most accessible formal treatment of when to commit to a known option versus continuing to search under uncertainty.
About the image
One of the many exhibits at the London Bus Museum at Brooklands.
Photo montage and photo by Matt Ballantine, 2026
Random the Book 