When knowledge isn't the problem
Context & Cringe did not begin as an attempt to create a game.
Over years of teaching application privacy in workshops and training sessions, we began to notice something subtle but persistent. The people in the room were engaged. They understood the rules, could explain regulatory requirements, and were comfortable discussing technical privacy threats and countermeasures. From a knowledge perspective, very little was missing.
And yet, when conversations turned to real design decisions, something shifted. Discussions that seemed clear in theory became murkier in practice. The issue was not a lack of understanding. It was a gap between knowing the principles and recognising their impact in context.
Privacy is not abstract - it is contextual
Application privacy is complex, nuanced and deeply contextual. Most of all, it is both very technical and deeply human.
In our broader work on privacy threat modelling, we describe privacy analysis as consisting of multiple conceptual layers: the feature itself, the surrounding system and technical ecosystem, the business context and rationale, and the wider environment that shapes legal, cultural and social expectations. Looking at functionality through only one of these lenses inevitably misses part of the picture. Privacy consequences rarely emerge from a single dimension; they arise from the interaction between layers.
The same data point can feel entirely acceptable in one situation and deeply uncomfortable in another. A feature that appears harmless when considered on its own, can feel intrusive once it is placed within a different app, aimed at a different audience, or combined with other elements.
What we observed repeatedly was that teams tended to evaluate these decisions analytically. Conversations centred on legality, intent and confidentiality. Those are essential considerations, but they do not capture the whole picture.
In many cases, the most meaningful turning point in a workshop did not occur when someone referenced technical privacy frameworks or data protection regulation. It occurred when someone reacted instinctively and said, “That feels wrong.” That moment, often brief and understated, carried more weight than any formal explanation, because it revealed something that rules alone could not. We could literally see the visceral reaction on their face, before they could even explain what they were thinking.
Designing backwards from a feeling
What makes the origin of Context & Cringe particularly interesting is that we were not trying to design a game at all. Their focus was on finding better ways to explain the nuances of “context” in application privacy and, more importantly, to give participants that visceral feeling that comes from truly understanding how privacy affects individuals.
We started from the desired outcome - that cringe feeling, and that recognition of how slight changes in context can amplify that feeling - and worked our way back.
In other words, the starting point was not “game” mechanics or format, but an outcome: the small but unmistakable moment when someone recognises that a combination of behaviour and context has crossed a line - and notices the nuanced details that caused the crossing.
From there, the questions became more practical. How could that reaction be surfaced deliberately, rather than accidentally? How could it be recreated consistently across different audiences? How could it be experienced safely, before anything is released to users?
The deeper they explored these questions, the clearer it became that explanation alone would never be sufficient. Context is not absorbed passively. It has to be experienced.
Beyond awareness
Much of what would eventually become Context & Cringe grew organically out of our training content. Exercises that compared scenarios, encouraged contrast and invited open discussion consistently produced richer insight than those focused solely on teaching theory. Participants began to move beyond what was strictly permissible and into conversations about what felt appropriate, and why.
It was only later we recognised that this pattern could evolve into something more structured, more repeatable and more engaging. The origin, however, remains unchanged. The goal was never simply to increase awareness. It was to move beyond explanation and towards experience, to help people internalise privacy decisions rather than merely understand them.
Context & Cringe exists because explaining privacy was not enough. Real understanding required something that could be felt.
In the next part of this journey, we will explore how that philosophical starting point, designing backwards from a feeling, gradually took shape in a form that made nuance not only visible, but playable.
