Highlighting books for serendipity

Image: Notes in the margin of a Mallorcan noble’s book printed in 1748. Kind of like a mind map, isn’t it?

When I was younger I tried briefly to keep books nice and neat, ready to display, post-use, on a bookshelf – it seemed like that was the thing to do, the way to be. respectful of the text and to have display to the casual browser of one’s shelves not only that you were well-read but were also able to look after nice things.

Over time I came to know myself a bit better. I’m a reader who loves books – I want to get in and consume them – and I’m always starving for more. In the end I decided, switching metaphors, that my books worked for a living. They weren’t show-ponies, kept looking their best and worthy of rosettes fro presentation – they were going to be put to work in the employ of my bookish appetites.

Once I was over the keep-them-neat syndrome, I was much happier to mark them, to highlight things that I wanted to remember. I settled on a system of scoring horizontal lines with my thumb under passages and then indicating that there was a highlight on the page buy dog-earing the bottom of the page. That way I could review the key passages easily without having to worry about taking notes or inserting marker slips or post-its.

When e-books came along, the highlighting of text was a one of my favourite features of this format. In non-fiction books, I’ll often highlight up to a 100 or more passages (fiction books, even ones I enjoy, I tend to highlight less – and then only passages where the language or an idea has stopped me in my tracks).

Like the paper scoring and folding approach to highlights, the highlighting was probably as much about pausing and noting the text as setting down markers that I would ever return to – and while this was useful enough, every now and again I would need the ideas from a book for a project and could seize it and go quickly through the highlights to find useful reminders of ideas or pointers for further research.

Image: A highlight from the must-read chronicle of the first 200 days of the Trump administration, Fire and Fury.

Every now and again, when a book seemed especially important to my work, I would use the highlights to help me fillet it and share the key ideas and insights with colleagues and clients. I read a lot more books than a lot of people, but still can’t read all the books I want to – – I think of The Hard Thing About Hard Things, Creativity, Inc., The Checklist Manifesto and, recently, The Four by Scott Galloway – sharing fillets or excerpts I realised was a lot more useful than demanding that everyone should read a certain book. When I simply couldn’t wait for everyone to read them they needed to know about these ideas now and a briefing on the book might not only urge them into reading the whole thing, but at least have a clue about why I was suddenly obsessed with certain concepts.

There was a function in the Kindle notes and highlights website – I read most e-books, indeed most books, on the Kindle platform – where you could create flashcards of text that you’d highlight. Using a learning algorithm based on how many times you need to be exposed to a text to remember it. This was great – I created a short-cut on the home page of my phone to be able to review it.

There were two powerful bits of magic at work here. First, I was reminded of passages – ideas, bits of data, advice – that I’d read and loved but since completely forgotten. Second, it was a brilliant way to make my brain lucky – to recall things at a moment that would be incredibly fortuitous. It’s amazing when this happens, and it has happened to me a lot – a key quote popping up a day or so before delivering a big speech, or a bit of hard-won experience from an entrepreneur popping up just as I am in the jagged grip of a decision-making dilemma.

As a side note, getting lucky with knowledge and ideas is incredibly motivating. It seems to me that it pushes you into a “toward state” – seeking, curious, engaged – and that can be incredibly helpful.

The problem with this approach was that I often drifted out of the habit of using it – usually after a burst of clearing away clutter from my phone’s home screen.

Recently, an app was released and has been developed nicely, that takes your highlights. Readwise sends you a daily email with a handful of quotes to review. You can also click through to a web app which allows you to tag quotes, and share them with other apps.

Image: Reviewing a quote in Readwise. 

I’ve also been using it as a relatively a passive way of collating quotes and research for my new book idea’s outline. I share the quote to my task-app Omnifocus as an action to add it to Scrivener, a powerful manuscript editor. When I have a spare moment, or a few Scrivener tasks have built up, I open that app up and have a few minutes slotting the quotes into the structure and thinking about how the book outline is shaping up.

If you highlight books on Kindle, I highly recommend trying out Readwise, it’s a simple service that can prompt all sorts of useful ideas and thoughts and, as is the case with my book idea, fit into some useful work-flows without creating extra chores.

: : Bonus Kindle highlighting tip – Diigo, the excellent bookmarking service, has recently added a feature that lets you bookmark / add to your library all of the highlights from a Kindle book. Really useful if you use that service – and if you don’t, you really should…