Hello Octopress!

A few days ago I stumbled upon a neat project named Octopress:

Octopress is an obsessively designed framework for Jekyll blogging. It’s easy to configure and easy to deploy. Sweet huh? – Octopress

Sweet indeed! The more I read about it, the more intrigued I became. After a few hours spent exploring the code, importing the posts/pages from my Wordpress install into Octopress, and tweaking the default theme to my taste, I've taken the jump and moved my site over to using the Octopress platform.

Octopress is a simple blogging platform aimed at hackers. It's built around the Jekyll engine, which is the blog-aware static site generator that powers Github Pages. The "database" for the site is simply a collection of flat text files using Markdown (or Textile) mark-up. You can setup either "posts" or "pages", all as you'd expect. When you're ready to deploy, you use Rakefile automation to "generate" the static site files.

It also has a great default theme (IMHO) – very clean and simple – which was actually my original attraction. It was only after reading more about the project that I realized it had huge appeal to my geek-side too.

Why Octopress?

It was Matt Gemmell's "Blogging With Octopress" post which resonated the most with me:

WordPress is excellent, but it’s over-featured for what I need, and its PHP/MySQL guts are opaque. I don’t really like the idea of all my writing being inside a big database either; it’s a single point of failure, and that makes me uneasy. – Matt Gemmell

For what I do with my website, Wordpress was overkill. It ended-up being Yet-Another-Thing-I-Needed-To-Maintain-Security-Patches-On™.

I was immediately attracted to the simplicity which Octopress provides: editing pages and posts as plain-text text-files, all static files so no security-patches or vulnerabilities to worry about, and easily portable and backup-able. It combines a lot of things which I have grown to love: I can keep all my content in a Git repository so that I can publish from multiple locations (if need be), I can work on the site entirely in text (vim + screen), and it's dead easy to deploy and backup.

Migrating from Wordpress

It really didn't take that long to migrate everything over to Octopress.

It took a few hours to get a cleaned-up import of my old Wordpress content. Based on the recommendation of others, I used exitwp to create Jekyll-style posts based on my Wordpress content. This went fine for the most part, but there were some parts in the Wordpress export file that I needed to fiddle to keep the exitwp script from crashing. The end result was that I had a directory full of simple *.markdown files which represented all the content from my Wordpress site. I spent a few hours going through those files and cleaning up the Markdown syntax until it matched what I wanted. Some of my original Wordpress posts were a mixture of Wordpress mark-up and raw HTML, and that threw the exitwp parser for a loop in some places. It did a great job overall though.

From there, I spent some time looking through the guts of the Octopress source code getting acquainted with things and seeing how I might be able to fiddle with some of its inner fiddly-bits. It's written with native support for customization, trying to keep a clear separation between the core "code" of the site (which can be overwritten during a future upgrade) versus any "customization" files which the user might make changes too. It's a fantastic paradigm and one that you don't often see too much of in projects.

Last but not least, I spent some time tweaking the theme to my tasting (…a bit of pepper here, a bit of salt there…). As I mentioned above, it natively carves out files which are earmarked for user-customizations, where you can tweak the CSS (SASS), colors, page/sidebar dimensions, etc. It's all just extremely well-thought-out and a joy to use and extend.

Ending Thoughts

This has been a fun pet project for me. It's the first time I've used a Ruby environment. It's also the first time I've played with SASS (*.scss), and boy is it going to be hard to go back to writing plain-old CSS. SASS's color functions are ridiculously slick: being able to do things like desaturate(lighten($nav-bg, 8), 15) in a *.scss file is awesome and makes tweaking a site's color-scheme oh-so-much easier.

I'm a bit sad to have lost the lifestream (wp-lifestream) functionality from my old Wordpress site. But then again I'm already doing full exports of most of my lifestream'd websites (Google Reader, Delicious), so it might not be too hard to generate static lifestream pages using a cronjob or something. That's a project for another day…