For academics, the early stages of a writing project should be a time of exploration and discovery. Yet the tools we use often constrain our thinking in subtle but powerful ways.

Most of us default to writing in linear documents like Google Docs or Word. While these tools excel at many things – including collaborating with colleagues around the world – they enforce a regimented structure that can stifle creative thinking. You start at the top and work your way down, with each thought following the next in orderly succession.

But what if there’s a better way to capture ideas when they’re still forming?

What is structured serendipity?

Recently, Ben Gordon and I found ourselves frustrated with this linear approach during the early phases of a collaborative writing project. Our solution was what I’ve come to think of as “structured serendipity” – a mindful approach to creating spaces for non-linear thinking within well-defined boundaries.

Structured serendipity provides enough focus to keep your thinking relevant to your project, while allowing flexibility for surprising connections to emerge organically between concepts. It’s about creating conditions where ideas can collide in unexpected ways.

Breaking free with Obsidian

To implement this approach, Ben and I set up a shared Dropbox folder containing plain text files that we could edit in Obsidian, a note-taking app designed for connected thinking.

What made Obsidian different from our usual tools?

• We could have multiple notes open side-by-side, making it easy to develop parallel threads of thought
• We could seamlessly link between related ideas without forcing them into a rigid structure
• We didn’t need to worry about formatting or document structure – we simply captured thoughts as they came
• Ideas could spread out in a more natural, web-like fashion that better reflected how our thinking actually works

The result felt like a playground for ideas rather than a production line. Our thoughts could branch, merge, and evolve organically without the pressure to immediately fit them into a linear narrative.

The benefits we discovered

This experiment yielded several advantages that traditional writing approaches couldn’t match:

• More novel connections – Ideas that might never have encountered each other in a linear document naturally intersected
• Reduced cognitive load – We didn’t have to maintain a complete mental model of the entire document structure
• Greater collaborative flexibility – Each of us could pursue threads of interest without disrupting the other’s thinking
• Preserved context – Related ideas stayed connected even as the project evolved
• Enhanced creativity – The freedom from structure allowed more divergent thinking

While we’ll eventually need to wrangle our ideas into a linear form for sharing, the ideas themselves are richer and more nuanced thanks to this non-linear exploration phase.

How you can implement this approach

Here are some practical steps to try this non-linear approach to collaborative writing:

1. Choose the right tool – Obsidian works well, but so do other connected note-taking tools like Roam Research, Logseq, or even simple mind-mapping software
2. Define boundaries – Establish what your project is and isn’t about to provide productive constraints
3. Start with seed notes – Create a few initial notes with core concepts to build from
4. Embrace fragmentation – Don’t force all your thinking into one place; let ideas live in their own notes and connect them later
5. Set aside dedicated exploration time – Schedule periods specifically for non-linear thinking before attempting to organise
6. For collaboration – Use a shared folder in Dropbox or a similar service to allow multiple contributors

Final thoughts: Creating space for connections

Every academic needs to find their own workflow for productive thinking and writing. But if you’ve been feeling stuck in a linear rut, creating space for more open-ended ideation might be just what you need.

The most valuable insights often emerge not from methodical progression, but from unexpected collisions between ideas. Structured serendipity gives those collisions space to happen.