Experience improves decision-making up to a point. Past that point, the schemas that success has reinforced begin to filter new information in ways that make the environment look more familiar than it is — and make the decisions that the changed environment requires feel genuinely wrong. The cognitive entrenchment that success produces is invisible to the person it has happened to, which is precisely what makes it consequential.

How success reinforces the schemas that built it

Dane’s (2010) cognitive entrenchment research provides the foundational mechanism. Success reinforces the schemas that produced it: the strategies, heuristics, and frameworks through which the entrepreneur perceived opportunities, evaluated options, and made decisions that worked. Each success makes those schemas larger, more complex, more interrelated, and more stable. Each application of a schema that produces a positive outcome deepens the schema further — through exactly the reinforcement learning mechanism that makes habits automatic.

The danger is not that the schemas are wrong. In the environment where they were calibrated, they were right — which is why they produced success. The danger is that the schemas developed in one environment are being applied to a different one, and the deepening that made them powerful also makes them rigid. The successful entrepreneur applies their schema to new situations not because they have evaluated its applicability but because the schema is so deeply embedded that it activates automatically — and its activation feels like insight rather than habit.

The subjective experience is the specific problem. The entrepreneur whose success has produced cognitive entrenchment does not experience themselves as applying an outdated framework. They experience themselves as applying deep expertise to a new problem. This is subjectively indistinguishable from genuine expertise until the environment changes faster than the schema updates — at which point the entrepreneur is genuinely confused by a market that has stopped responding to the approaches that previously worked.

The attentional mechanism that blocks better solutions

Bilalić, McLeod and Gobet’s (2008, 2010) Einstellung research provides the specific attentional mechanism. When a problem with structural similarities to a previously solved problem is encountered, the familiar solution is activated automatically. This activation does not simply make the familiar solution available — it actively directs attention away from the territory where alternative solutions exist. The chess players in their research could not see the more efficient solution because their attention had been captured by the familiar solution and could not be released from it through deliberate effort alone.

For the successful entrepreneur, the Einstellung effect operates on market problems, hiring decisions, and strategic choices. The entrepreneur who successfully navigated a previous competitive challenge through aggressive pricing approaches new competitive threats with the pricing solution already activated — which makes it structurally harder to perceive the repositioning solution that the changed competitive environment actually requires. The familiar solution is not considered and rejected; it prevents the perception of the alternative in the first place.

What 300 expert forecasters established about success-induced rigidity

Tetlock’s (2005) Expert Political Judgment research, conducted across 300 experts over 20 years, provided the most rigorous empirical documentation of success-induced rigidity. The “hedgehogs” — deep specialists who organised everything through a single powerful explanatory framework — showed systematically worse prediction accuracy than the “foxes” despite significantly higher confidence in their predictions. The mechanism is Dane’s cognitive entrenchment at the forecasting level: their investment in a single framework had made it so stable and available that it organised new information whether or not the new situation genuinely belonged to the framework’s domain.

The most important finding is the confidence-accuracy relationship. Hedgehog confidence was positively correlated with their investment in their framework and negatively correlated with their accuracy. The more successful the framework had been — the more thoroughly it had been reinforced through past correct predictions — the more confidently it was applied to situations where it no longer applied, and the more systematically wrong the predictions became.

The organisational version: competency traps

Levitt and March’s (1988) research on organisational learning documented the competency trap — the tendency for organisations to increase their competence in successful activities at the expense of exploring alternatives. The mechanism operates through the same reinforcement pathway as individual cognitive entrenchment: success in a capability makes it more available, more efficient, and more deeply embedded in organisational routines, while simultaneously reducing the exploration of alternatives that might produce superior performance as conditions change.

Nokia’s failure to respond to the smartphone is the most thoroughly documented case. Their leaders had genuine, deep expertise in mobile phones — and that expertise produced the cognitive architecture through which the smartphone’s disruption could not be perceived as disruption. Their schemas directed attention toward the new device’s limitations relative to existing products rather than toward its definition of a new product category. Their industry expertise was not a neutral asset; it was the specific cognitive architecture that filtered out the signal they needed to receive.

What the outside view corrects and how to access it

Kahneman and Tversky’s inside view versus outside view distinction provides the most practically applicable debiasing mechanism for success-induced rigidity. The inside view — the application of specific experiential details to a new situation — is the mode that cognitive entrenchment produces automatically. The corrective is the outside view: what is the base rate for situations structurally similar to this one, across all comparable cases, regardless of the specific details of my previous experience?

The outside view forces a confrontation with the possibility that this situation is not as similar to the previous success as it feels. It requires the entrepreneur to specify the reference class — what category of situation is this actually, at the structural level? — and to use the base rate for that category rather than the inside-view estimation that their schemas generate. This is cognitively uncomfortable precisely because it requires holding the schema’s confident answer at arm’s length and asking whether the situation actually belongs to the schema’s domain.

Lovallo and Kahneman’s (2003) Harvard Business Review account documented how systematically executives fail to take the outside view about decisions in their domain of expertise — and how reliably this produces the optimistic projections and the failure to anticipate disruption that successful entrenchment generates.

Cross-domain exposure as structural prevention

The most reliable structural prevention for success-induced cognitive rigidity is deliberate cross-domain exposure. Epstein’s (2019) Range research established that breadth of experience across multiple domains is the primary predictor of innovation performance in complex, changing environments precisely because it prevents the single-schema deepening that success in one domain produces. The entrepreneur who regularly engages with problems, industries, and intellectual frameworks outside their domain of success is maintaining cognitive flexibility through the specific mechanism that entrenchment threatens — the availability of multiple non-entrenched schemas that can be applied when the entrenched one is failing.

This is not a recommendation to avoid deep expertise. It is a recommendation to pair deep expertise with structured exposure to environments where that expertise does not apply — where the schemas are not calibrated and the entrepreneur must genuinely perceive the situation rather than pattern-match to the familiar solution.

Books worth reading on this

Being Wrong by Kathryn Schulz. Schulz’s account of the phenomenology of error — specifically the finding that being wrong feels subjectively identical to being right up until the moment of correction — is the most emotionally precise available treatment of why cognitive entrenchment is invisible from inside. Her account of how the feeling of certainty is a property of the belief rather than of its accuracy maps directly onto the Einstellung and hedgehog mechanisms: the confident expert applying their schema to a situation where it no longer applies experiences the same certainty as the expert applying it correctly. Seeking Wisdom by Peter Bevelin. Bevelin’s systematic account of the mental models that protect against cognitive entrenchment — covering the specific reasoning patterns of the most accurate long-term thinkers across multiple domains — provides the most comprehensive single-volume reference for the cross-domain thinking practices that Epstein’s Range research predicts will maintain cognitive flexibility as expertise accumulates.

If the dynamics described here are significantly affecting your wellbeing, speaking with a psychologist is the right next step. UK: Samaritans (116 123, free, 24/7). Mind (0300 123 3393). BACP: bacp.co.uk/search/Therapists. Crisis Text Line — text HOME to 741741 (US, UK, Canada, Ireland). International: internationaltherapistdirectory.com.

This article is for educational and informational purposes only. Sources: Dane, E. (2010), Reconsidering the Trade-Off between Expertise and Flexibility: A Cognitive Entrenchment Perspective, Academy of Management Review, 35(4), 579–603. Bilalić, M., McLeod, P. & Gobet, F. (2008), Why Good Thoughts Block Better Ones: The Mechanism of the Pernicious Einstellung (Set) Effect, Cognition, 108(3), 652–661. Bilalić, M., McLeod, P. & Gobet, F. (2010), The Mechanism of the Einstellung (Set) Effect: A Pervasive Source of Cognitive Bias, Current Directions in Psychological Science, 19(2), 111–115. Tetlock, P.E. (2005), Expert Political Judgment, Princeton University Press. Levitt, B. & March, J.G. (1988), Organisational Learning, Annual Review of Sociology, 14, 319–340. Kahneman, D. & Tversky, A. (1979), Intuitive Prediction: Biases and Corrective Procedures. Lovallo, D. & Kahneman, D. (2003), Delusions of Success: How Optimism Undermines Executives’ Decisions, Harvard Business Review, 81(7), 56–63. Epstein, D. (2019), Range: Why Generalists Triumph in a Specialised World, Riverhead Books. Kay, J. (2010), Obliquity, Profile Books. Schulz, K. (2010), Being Wrong, Ecco. Bevelin, P. (2007), Seeking Wisdom, Post Vestera Media.