Migrating From Octopress to Squarespace

Unlike most other articles related to Octopress and Squarespace I am actually moving to Squarespace from Octopress.

I came to know about Octopress right around the time other people were talking about why static blogs were a better option than a) running a full blown CMS for yourself and b) hosting your blog on a service. I won’t go into the arguments about whether that’s true or not, but I bought into it. I used to run a Drupal site for myself, and when I started spending more time on Drupal security patches than I added content, I switched to use Blogspot. That worked for awhile, and you can read why I left that service. I toyed with Jekyll, gollum and some others, but ended up using Octopress.

I loved just about everything Octopress offered. It was really easy to generate my post, write some Markdown, and then deploy, all from the command line. The content was stored in git, which meant I could edit my blog from pretty much anywhere I wanted to without worrying about losing content. The default/only theme looked fine for my purposes, and with Typekit and Google Fonts I could customize what I wanted to. Everything was great right? And then, one time, I tried merging from the upstream branch to get changes they’d made to the Octopress core.

So that didn’t go very well. I decided I’d put it off for awhile since everything seemed like it was working, though I started to wonder if I was missing out on a cool new feature or some security issue. I also started to really feel the burden of hosting my own server. I was using a Linode server that was running a web service for my ill-fated iPhone app at the time, so having another virtual host was no big deal. After all the TLS issues in the last couple of years, again like with Drupal, I felt like I was spending more time with security updates than I was actually making content.

So when I read this post about how Octopress was going to change, I knew the day of reckoning had arrived. I either needed to wait to see what Octopress 3.0 was going to be about, or switch to an alternative. Then, I remembered Squarespace.

I created a a Squarespace page back in 2012 based on hearing about it on… well… every podcast ever. I didn’t do much with it, but I re-opened my account this weekend and started the (somewhat painful) process of importing my blog Markdown files into Squarespace posts. It seems like I am stuck using some ancient version without all the bells and whistles they advertise today, so I guess I have upgrading to that to look forward to. In the meantime, I am fairly happy with the results and can safely shutdown my server and not worry (much) about security problems and software upgrades.

I do not regret using Octopress, I really liked using it and I think it’s been a great project for anyone that wanted a slick static blogging system.

Now my only problem is figuring out what to write about…