Optimising for books

I spent years resisting buying a Kindle, because I knew that it would mean the end of paper books (for me, at least).

I enjoy the tactile interaction, the smell, the sensation of turning a page; all rich, sensory experiences. But eventually, I found myself caught without a book, unexpectedly finishing what I was reading, not being able to get hold of that particular sequel, or damaging my back carrying around a couple of bulky fantasy tomes in a satchel one too many times. And so, to avoid that feeling of desperate booklessness (and bruised shoulders),I sacrificed paper and embraced digital.

Now, I have my entire library in my bag or in my pocket, just a ‘click’ away. And I’ll never go back to paperback. Because, whilst I miss browsing by cover and reading the back and inside pages and turning pages in bed, the efficiency with which my reading library and activity is now managed makes the crude, analogue interaction I have with books on dusty shelves seem archaic.

My total conversion to Kindle, however, is less about the device itself, and more about how I effectively I use it, and how I manage my reading. You see, I’ve optimised my reading experience. And I’d like to share the software, setup and processes which enable me to seamlessly synchronize, catalogue and manage my literature, so that you can, too.

*Note that I’m a heavy Windows and Android user, and whilst most of this should be adjustable to fit, your mileage might vary.


At the heart of my reading ecosystem sits Calibre. It could be lazily described as ‘iTunes for books’, as, with minimal setup, it does a great job of ‘albumifying’ your books, syncing to and from your kindle (and other devices)*, and allowing you micromanage metadata and collections. Calibre is a great tool for minimising what’s actually stored on your device at any given time, as well as managing what you’ve read vs what you haven’t, and other useful info.

It’s worth customising and playing a little – there are a ton of settings, including the ability to create custom columns, which I find particularly useful for marketing which books I’ve read, and some other bits and pieces.


It’s worth investing the time in tweaking book titles to separate their series from their titles (don’t forget to map any versions you have on your device to the updated version), just to keep things clean and tidy.

*I should point out that, in some cases, the content format stored on the Kindle device (particularly with some of the more recent Kindle models) cannot be directly exported to / synced with Calibre. In these cases, you can still go through your Amazon account and download the files. Hopefully somebody will have a less cumbersome fix shortly.

Calibre Cloud


Calibre really starts to come into its own when you start extending it and adding building blocks around it. In particular, the Calibre Cloud app adds some serious punch by moving your entire library to the cloud (or more specifically, to your DropBox folder), and syncing it to your phone – allowing you to easily send and browse books on the fly. Of course, the added benefit of running your library from DropBox is that it becomes incredibly easy to sync and share your whole library with family or friends (though you should of course consider the legal/piracy implications here – though Amazon is impressively liberal around ‘family’ sharing).

For bonus points, the pro version of the app allows you to push files straight into the Kindle app on your phone, without having to email the file across.

Calibre DeDRM Tools


If you’re reading content on multiple devices, or need to convert the format, you may run into some DRM challenges. Apprentice Alf’s blog provides provide a Calibre plugin which you can calibrate to your own Kindle or device’s ID, which will automatically strip out DRM at the point when you add a file to the library (as such, if you intend to use/need this, it’s good to get this set up early – although you can export, delete, and re-import files to get around this).

Of course, this plugin could be used for evil, so for the sake of clarity, I’ll quote the website which hosts the plugin,

Please only use this application for gaining full access to your own ebooks for archiving/conversion/convenience. De-drmed ebooks should not be uploaded to open servers, torrents, or other methods of mass distribution. No help will be given to people doing such things. Authors, retailers and publishers all need to make a living, so that they can continue to produce books for us to read. Don’t be a parasite.

Goodreads Integration


With a large library of books in play, it’s easy to forget what you’ve read, what’s on your ‘next up’ list, and so forth. This is something which Goodreads does reasonably well, and if you’re using a relatively recent generation of Kindle, you’ll find that Goodreads is automatically integrated into your device (they’re owned by / part of Amazon, and have been for quite some time), and that when you review and ‘share’ your completed books, it syncs the ‘completed’ status to Goodreads.

This is powerful, because it means that syncing your Goodreads account back to Calibre closes the feedback loop on what you’ve read. This plugin does the legwork of connecting your account, and makes it easy to use bi-directional syncing (individually, and en masse) between your Calibre library and Goodreads data.

Bonus tip – Articles

Reading can’t all be for leisure, right?

That’s where kit like Send to Kindle for Chrome comes in. It’s great for pushing the content of web pages or articles to your Kindle with just a click.

If you use Pocket to manage your consumption of articles, it’s worth looking at P2K, which allows you to schedule automatic and intelligent pushes from your Pocket account to your Kindle (the paid version, at ~$3, lets you specify a tag).

If you want to get really clever, you can build processes whereby Calibre classifies and stores these articles differently/separately, and build out not only your reading library, but the articles you plan to read, editorial, newspaper pieces, and just about anything else.


There’s still a lot of admin involved, I’ll give you that. This is a degree of micro-management which, a few years ago, I’d never have imagined investing into my books. It’s intimidating, initially, but it’s worth investing it.

…Because your book collection is only going to get busier, and messier. The rise of Amazon, Kindle and self-publishing has lead to a proliferation in the creation and distribution of new literature which has changed the way in which I – and all of us – read. Books are easier, cheaper and faster to purchase. Furthermore, increasingly, the new model is for teaser books (the first in a series) to be completely free in order to get you hooked, and the series themselves become increasingly composed of more-shorter books to recoup the value. So now I grab free books preemptively, in the knowledge that I’ll get to them eventually. I have hundreds which I’ve never looked at – yet.

I’m vastly quicker to acquire books, and to store them for a rainy day, with no risk of running out of shelf space – at a pace which would have been unthinkable without a Kindle. Managing this volume of books with shelf space, or even with a Kindle but lacking Calibre or an equivalent, would be nightmarish.

Without this system, I’d be piling up epub files in an ever increasing tower, never quite knowing what I’ve read, what’s next, or even what I’ve got. So I’m putting my eggs in this basket as the way I’ll manage my library for the foreseeable future, so it’s worth getting it right, and making sure it’ll scale and survive as it grows.

What’s your system? What have I missed? What do you do differently?

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