More Muc Than You Can Handle

Migrated to Octopress!

It’s funny how many posts there are from people who have migrated to Octopress. What would motivate someone to post their migration experience? I think I understand why. It’s such a shift in thinking that it’s worth talking about. My migration experience was so much pleasant that I feel that I must let everyone know.

So what’s my motivation for moving to a new blogging platform? Was what I was using before broken? Not exactly, but I didn’t enjoy the blogging experience that much because I found the experience to not be a lot of fun. I want to start writing more and feel that removing any barriers to this activity will get more content out there. I also didn’t like having to rely on a server side application server. For a website that changes around 30 times a year, a database backed content management system was overkill. Also, the website was hosted on a friends server that I had no backups for, and didn’t want to spend much effort creating a backup/restoration strategy.

After some searching, I found jekyll, wich I love for its simplicity. I was going to use bare bones jekyll but then I was directed to Octopress which is a framework to make working with jekyll a lot easier.

Since I was on Windows my install was a bit different than the documentation. Luckily I have created a tool to make ruby installation simple on Windows. Here’s everything I did to go from nothing to having a working blog hosted on github!

  1. Installed yari, and got my environment using ruby 1.9.2
  2. Followed the octopress setup instructions
  3. Followed the octopress deployment instructions

I was blown away when I saw my blog appear when I went to


Unfortunately my previous blog engine’s export functionality is broken so migration had to be manual. Every post is going to be copy and pasted and re-linkified in markdown syntax. I wanted to get this new version up and running first so I made a few compromises.

  1. I decided not to migrate every post. Some of my old content doesn’t really fit with the rest of the content so I decided to abandon the posts. I’m keeping the old blog up and running so that people can still find the posts there if they really want them.
  2. Keeping links working is extremely important to me. Octopress provides the ability to set the permalink on an individual post which made this element of the migration super easy. Every blog post has “front matter” which is a little bit of YAML meta data. Adding a permalink value will make the post accessible from that URL path: permalink: /foo/bar/post
  3. I went live with an incomplete migration. I only have about a third of my posts migrated. I did this so I can get this live and sort out issues right away before everything is migrated. Also, it’s a way to motivate me to get everything into the new blog ASAP.
  4. Added a custom 404 to guide those who want to see non-migrated content to the old blog.
  5. Added “” to my CNAME file. I followed the instructions here. Note that this is enabled for non-paying users now! I use for my DNS and updating the A record and CNAME (for www) was a snap.

Other Stuff

When setting up the blog I had an online discussion about how url design. I decided to leave dates out of my url and to include them in the title slug only when appropriate. I came to the conclusion that url slug design is extremely important and doesn’t always have to be word for word related to the post title. Because Octopress is so easy to configure, the configuration setting for this is simply this value in _config.yml:

I’m now using other 3rd party services like feedburner, disqus, and With all of these things taken care of for me, authoring a post is a call to rake new_post[“post title”], edit in vim, and preview using rake preview to view the changes before I deploy them.

The one thing I would like to change is learn how to create a custom theme. It’s quite common to see a lot of octopress based blogs use the same default theme that I’m using now.


Octopress is awesome! I love the workflow for authoring new content. I much prefer markdown over using some WYSIWIG editor over a web connection. The ability to do everything local means there’s significantly less effort for me. I believe Octopress is an excellent example of how an excellent deployment mechanism can shift how work can be done. If pushing brand new code to production is that easy, it removes the need for complex server side code.

Lastly, if you would like to see what a raw blog post looks like, take a look here.