I was scanning through lobste.rs and found this post on organising bookmarks by Josh Leeb and of course I was interested. もちろん!

So far, I’ve added 116 bookmarks to Pinboard, which is hardly a large number. Yet, keeping them organized has already become a challenge. And it’s a hurdle for wanting to add more and continue using Pinboard.

Organising bookmarks with tags

The primary way bookmarks are organised is with tags. You give one word or multiple word descriptions of the bookmark. For example nytimes.com could be tagged with nyt, nytimes, news. These are user generated tags and as you can already see it is very subjective. The idea is to associate a word or words to the bookmark that makes it easy to find later.

From the first time I used Pinboard, I was already asking myself what sort of tagging structure to implement. I didn’t want to over-engineer some complex system, I just wanted it to be simple. But most of all, I didn’t want adding bookmarks and maintaining tags to be a chore. It should feel effortless, and only take a couple of seconds.

The cognitive load of deciding which tagging system to use is unnecessary in my opinion. This presents and opportunity for innovation. Could AI help with this? Could we replace tagging with search instead? AI and search are ubiquitous these days. A low-tech solution is to provide suggested tags from your collection and system suggested tags probably based on what most people are using to tag that url.

Organising bookmarks by projects

The final problem with basic tagging also has to do with context. Not of terms, but of projects.

I work on a lot of research-heavy projects, or projects that are inspired by blogposts. And as the project continues more and more articles and resources are amassed. However simple tagging isn’t well setup to help collecting links in this context.

I can see the need to group bookmarks according to a project, that way you can go to a /projects route and see all the bookmarks connected to that project. For example if you're working on the Millennium Falcon project, you can have a /projects/millenium-falcon and see all the bookmarks you have saved for that project.

Possible Solutions

I’ve been thinking about an alternative approach for organizing bookmarks. One that solves the problem of overloading terms, helps with near-duplicate tags, and has first-class support for project specific bookmarks.

This approach involves a system of tagging using a hierarchical namespace, and persisting filters on the hierarchy into collections.

Josh spells out his solutions in his post which involves the projects route and having a collections route, it is really worth a read if you're interested in this kind of thing as I am.

Dear future self, make a note to add Josh Leeb to the alpha of Brief.