Over the past year I’ve been using a service called Readwise.io to surface highlights from books I read on my Kindle and from articles I read on my iPad using Instapaper.

The service has its flaws but all in all has been useful to me in helping me to remember what I’ve read and found important.

That said, I’m finding myself less inclined to wanting to read long form journalism on my iPad, especially at night in bed when I’m trying to stay away from screens or at the beach where my Kindle feels easier to read than my iPad.

I have spent the past couple of weeks cobbling together a collection of tools that makes reading long articles on my Kindle easier as well as saves any article highlights I’ve made to Readwise.

I wish that I could use Instapaper for this workflow but, while you can read Instapaper articles on the Kindle pretty easily, tracking highlights doesn’t work so well. So I’ve landed on the following:

Push to Kindle from fivefilters allows me to easily push web articles to my kindle from my Mac (via Safari extension), iPhone or iPad (nice, easy to configure dedicated iOS app)

I then read/highlight on my Kindle paperwhite

When I plug my Kindle into my Mac’s USB connection, the highlights are automatically sent to my Readwise account

This last bit requires a good bit of AppleScript sorcery but it’s pretty easy to achieve using EventScripts.

Basically, EventScripts notices when my Kindle is plugged in. Once it sees the Kindle is plugged in, it executes this AppleScript which emails the My Clippings.txt file automatically to readwise who then imports it.

Really pretty elegant stuff here that, I hope, shows the value proposition of many small/lightweight tools loosely coupled as opposed to some monolithic solution.