Creative thinking with Obsidian

In this video I’m talking to Ben Gordon about an experiment in creative thinking with Obsidian, which we tried in the early stages of a writing project. We were frustrated with the limitations of working in Google Docs. Even though Docs is great for many purposes – including collaborating with someone on the other side of the world – it still enforces a linear way of working. You start at the top and work your way down, one thought follows the next in an almost regimented way. For free-flowing idea exploration at the earliest stages of a project, this structure felt stifling.

So Ben and I decided to experiment. We set up a shared Dropbox folder containing plain text files that we could edit in a note-taking app called Obsidian. In Obsidian, we could have multiple notes open side-by-side, seamlessly linking between them and letting ideas spread out in a more natural, web-like fashion. We didn’t have to worry about formatting or structure—we could simply capture our thoughts as they came, while still maintaining connections to related ideas.

Read: Increase your writing output with distraction-free text editors.

Structured serendipity

I’ve been thinking of this approach as ‘structured serendipity’ where there are some boundaries to what we’re thinking about, that nonetheless opens up spaces for each of us to be surprised by the connections between ideas that come from the other person.

It felt like a playground for unexpected connections to emerge organically between concepts. The core idea of ‘structured serendipity’ is about intentionally creating spaces for non-linear thinking within well-defined boundaries related to your project. The boundaries provide enough structure to keep you focused, while the flexibility allows for surprise and creative leaps.

We’ll still eventually need to wrangle our ideas into a linear form—but we’re finding the ideas themselves are richer and more novel thanks to this little experiment in creative thinking with Obsidian.

Read: Using Obsidian for academic writing.

Of course, every academic has to find their own groove when it comes to productive habits and workflows. But if you’ve been feeling stuck in a linear rut, I encourage you to look for ways to create more open-ended spaces for ideation and creative cross-pollination within your writing process. You might just stumble into some unexpected insights.


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