The Compass Maker's First North: A Case for Deliberate Red Herrings in Site Structure

We are taught, from the very beginning, that clarity is the highest virtue in structuring a website. The goal is a frictionless user experience, a pristine information architecture where every path is logical, every signpost is clear, and the user glides from intention to destination without a single moment of doubt. We aspire to build digital supermarkets, where the milk is always next to the cereal. But what if, in our obsession with efficiency, we have paved over a fundamental aspect of discovery? What if the most direct route is not always the most memorable journey?

The prevailing wisdom is to eliminate dead ends and unnecessary forks in the road. A 404 is a failure; a confusing navigation menu, a sin. We wield redirects and canonical tags like pruning shears, cutting away any growth that doesn't serve the singular, towering trunk of our primary content. This creates a clean and manageable space, to be sure. But it also creates a predictable one. It assumes that every visitor arrives with a complete shopping list, knowing exactly which brand of cereal they want. It leaves no room for the browser, the curious soul who clicks a link not because it promises a specific answer, but because the wording is intriguingly opaque.

I want to propose a heretical idea: that a deliberately placed ‘red herring’—a link with an ambiguous or even misleading anchor text, a page that seems to branch away from the main topic—can be a powerful tool for engagement. Not as a dominant strategy, of course, but as a carefully considered accent. Think of it not as a broken signpost, but as a trail marker pointing towards a scenic overlook that isn't on the main map. The user who follows it may not find what they initially thought they were looking for, but they might stumble upon something far more valuable: a unexpected connection, a piece of supporting evidence they didn't know existed, a tangential idea that enriches their understanding of the whole.

The Value of the Unplanned Path

This isn't about creating a confusing mess. It’s about acknowledging that learning and exploration are not always linear processes. The most resonant discoveries often happen in the margins. By structuring a site with a few deliberate, yet contextually relevant, diversions, we mimic the way curiosity works in the real world. We invite the user to become a co-navigator of the content, rather than a passive passenger on a pre-determined monorail.

Critics will argue that this harms usability metrics. It might. A user might spend more time on the site, traversing a less efficient path. But what are we measuring? If the goal is sheer speed-to-conversion, then by all means, stick to the straightest line. But if the goal is depth of engagement, thoughtfulness, and the fostering of genuine interest, then perhaps a metric like ‘time spent exploring related but unexpected content’ is more meaningful than ‘seconds to find contact page.’

This approach requires a subtle hand. The ‘red herring’ must be a quality piece of content in its own right, even if its title is a bit cryptic. It must be relevant enough to feel like a serendipitous find, not a punitive dead end. It’s the difference between a museum placing a small, fascinating artifact from a different culture in a room of European paintings—sparking a new curiosity—and simply mislabeling a painting entirely. The former expands the world; the latter just causes frustration. In our quest for perfect information scent, let’s not sanitize the digital landscape of all its delightful, discovery-rich anomalies.

Notes & further reading

A few pages I came back to while writing this: