Exercising digital thinking and why Highlighter Pens are really bad

Insights, software showcase, and our manifesto for the transformation of content highlights

To fully utilize transformative technologies we have to move beyond our analog habits and our analog mindset. But what does that mean and how can it be practiced? How do you change an analog mindset to be a digitally transformative one? In this article, we want to practice it from the case of digital highlighter pens. You know, the act of highlighting sections of content in various colors. Something which, we argue, has hardly been digitally transformed at all! By the end of this article, we’ll use our findings to present a manifest for what “smart-content highlights” should be.

The field is stuck in a paradigm entirely based on these analogue metaphors of files and folders.“

Conor White-Sullivan

Conor, the founder of a promising and hyped note-taking tool called Roam, described brilliantly the current state of software for many knowledge workers – a field based on analog metaphors of files and folders. What we take from Conor’s quote and the interview led by Thiago Forte, a productivity expert, is that digitizing analog ways is way too common in software, too rare is real transformation.

Content highlights, its “tech-history” and future

We can summarize a big part of the current software field of content highlights and bookmark management in one paragraph. For online articles, the digital-savvy are likely working with tools like Pocket, Instapaper, or snippet-extensions to digital notebooks like Evernote and Onenote. The majority of digital-first users, however, likely stick to their PDF readers and their web browser bookmarks. This means that their highlights get stuck in each respective PDF file, just like color highlights with marking pens would be in a book. Let’s show what it might look like.

Software showcase

Pocket, slogan “When you find something you want to view later, put it in Pocket”

Saving Bookmarks in Pocket

Zotero together with a print-screen PDF, slogan “Zotero is a free, easy-to-use tool to help you collect, organize, cite, and share research”

Evernote with its web extension snippet, slogan “Evernote is the home for everything you need to remember, and everything you want to achieve”

What about ebooks then? Well, the highlight features are usually part of the reader-software that the ebooks you bought are connected to. For example, Kindle, Apple books, Google play books. If you want to move these annotations somewhere else, it is often by a capture-all-email address to Evernote and OneNote, or pure good old copy-pasting. Some platforms and tools, like GoodReads and Readwise, do have some integration where your highlights can be automatically imported, but they don’t really live up to expectations. A pretty good workaround for PDFs in regards to extracting annotations easily, we found in Zotero, a reference management software, used together with Zotfile, a plugin. This workflow can also be combined with Roam to get some cool effects. We’ll showcase this by the end of the article.

Software showcase

PDF-readers in this case “Preview”

Kindle’s content hightlight feature, slogan “Read ebooks and magazines”

Kindle together with a “Capture all-email-address” approach

Zotero together with Zotfile, an extension

But to better understand the digital transformation itself, we want to provide a history behind the landscape and the generational thinking that has shaped it. This is not a chronological history, but more of a story based on the digital maturity of the user. After, we’ll take a look at the future that should be demanded for content highlights!

The generations of annotations gone digital: past, contemporary, future

Generation 0: Printing out PDFs

More common than you might think, this is the people printing what they’ve got stored in files then grabbing their color sets of marker pens and going at it. To these users, the satisfaction of the tangible experience you get with the texture of paper is like a religion itself. Unfortunately, like religion, it can be consoling but not very efficient. Especially, if you need to work collaboratively.

Generation 1: PDF-readers becomes the key

These users like their books analogue, but have come to understand that for anything else, PDF is alright. They will be using whatever PDF-reader tools they have at their disposal (Apple Preview or Adobe Acrobat) and use its highlighting and commenting features. However, when you download a PDF they are sometimes locked and comments and highlights can’t be saved. For online-resources like web articles, these users save in PDF-formats, likely using Print Screen commands in the lack of something better. And understandably so, it doesn’t look like there is anything that much better on the software market. We’ve tried many. Long live CMD/Ctrl+P?!

Gen 2: A discovery of the ereaders

Now we’re talking about the really niched people. What characterizes the users of Gen 3 is the movement of notes and annotations outside the file or software-readers themselves into different note-taking systems before pasting them directly in word processors. When they move their notes and annotations, the typical approach is either copy-pasting, or exporting in various ways to their digital notebooks. For online resources they have discovered web-clipping extensions going directly to their digital notebooks, or smart bookmarking tools like Pocket or Instapaper. All shown previously in our software showcase.

Some digital savvy academics or researchers have taken it one step further. They use proper source- or reference management software like Zotero, Mendeley or Endnote. To extract annotations from their PDFs, which some do, there is the Zotfile extension for Zotero. The extracted annotations ends up in a HTML file which is stored as an attachment in the Zotero object. This makes for a compelling file library within Zotero, separating annotations from PDFs, while at the same time making it easy to create literature references in various writing softwares. However, this approach is far from perfect.

Now what does perfection look like? Enter Gen NEXT.

Gen NEXT: A manifest for smart content highlights

Ideally, you need a great PDF-reader tool that gives you the same kind of great reading experience that “.epub” software and other ebook formats provide. Whenever you create a highlight, being able to comment on it should be a standard-feature, not an exception. Another thing annotations of the future need is a lot more features. This is where the transformation really takes shape. Perhaps we can call it Smart-annotations or Smart-content highlights. To us, it would be something that provides…

A better experience of the context of where they were extracted. The digital experience right now of the surrounding content where annotations were extracted from originally needs to get better. A demo that gives a glimpse of what we want from the future, can be found in Roam used together with Zotero and the Zotfile extension.

Software showcase

Roam, slogan “a note taking tool for the connected thought”, combined with Zotero and Zotfile

One of the current limitations of Roam, is that you are free to set up the structure of each page and how to link between them. Great to cater for all individual needs, but bad to be able to run consistent analytics on top of your data. Also, we believe in building on each others’ experiences collaboratively. Because Roam starts as a blank page to build your own knowledge base on top of, it requires a lot of each individual, where you probably could be helped tremendously by using structures already developed by others.

Worthy of mentioning, there is also another plugin to Zotero where you can export your reference data including your extracted annotation in a JSON file. The JSON files (JavaScript Object Notation) can then be imported to Roam. That way you get all your Zotero references in the same format. This is a feature we’re currently toying around with ourselves and hope to demo more of in the future.

Separating annotations from the file-source and a full on library gathering all of your highlights. The tool Readwise gives us another glimpse of what an annotation library might look like in the future. Readwise is not yet usable for much else but nice emails of quotes from your highlights, but the thing that Readwise does well is how automated the extraction and access to your highlights are. Meaning, no manual or tedious copy-pasting! From a technical perspective however, Readwise requires downloading their app to extract the data for you, and we suspect it is using screen-scraping tools of Amazon’s webpage for your Kindle content online. Still, there is no official API for Kindle to get your annotations using code.

Software showcase

Readwise, slogan ”Don’t let your Kindle highlights disappear”

Filtering on various “source-types” etc. Smart tags and objects. Imagine having data-sets in Excel you couldn’t filter. Well, welcome to the software world of annotations! These kinds of smart features to work with your content highlights in a cohesive and collaborative system is really needed. Ideally you’d want a set metadata and tags to really get some analysis power behind your work.

Annotations beyond words. Remember a world without screenshots? Well, again welcome to the world of annotations. One of the principles we always talk about is that “all content forms are equal”. Podcasts, video clips, images – all should be easily highlightable. Currently, annotations and highlighting features are built for words. But in the modern world of content the strictly written word is far too limiting. Annotations only working with articles and books, is not good enough. We envision something applicable to any content format. Annotation features should be something available at the right-click of your very own mouse marker, undistinguishable even from a screenshot or a screen recording. If we want a small section of a video annotated, that should not be an obstacle. Want to add the video content together with an automated transcript? Yes, please!

Suggested highlights. When your content highlight library is growing, that should open up for some serious machine learning to give you suggestions of content that could be of interest. Annotations that are similar to each other should also be easily accessible. We’re talking groupings and perhaps semi automated meta-tagging in the form of organisations, individuals, relationships between various entities, word-classes etc. That means, your annotations are linked to specific database objects, representing that specific organisation. If it worked like that, it would be really easy to view in which content a certain organisation appears. Of course, the graph experience of the related content here should be highly visual and dynamic.

And, last but not least, collaborative! The world of highlight software right now is a lonely island. Something done alone, hard to replicate, and something that needs tons of work making understandable to someone else. In the future it needs to be easily understandable and accessible for anyone to view the annotations someone else has made. We have our own principle here for collaborative software. It goes like this: 

“If I would disappear but my work and data stays, how long does take for a colleague to take over where I left?”

Parsd principle for collaborative work.

That is a huge challenge presented not only to software, but also to the processes and workflows you have to design with it. 

What about you?

That’s our transformative manifest for content highlights and annotations. What do you think? How do you work with content highlights and annotations today? What are your wishes for future technologies?

Let’s keep the dialogue going. And follow us for more transformative thoughts. If there’s anything in particular you would like us to scrutinize or take a look at, please let us know!

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