Deciding to Move from Squarespace to WordPress

This site is still in its infancy. While it was created in March, I only started posting in earnest in May, and have steadily increased the frequency of content over the past couple of months. I’m managing a couple a week, along with relevant link posts. It is still early days, but the traffic is increasing, and interest is growing.

The site is currently built and hosted with Squarespace, which is a fine platform for any number of use cases. The advantages of using Squarespace are obvious, it is quick and easy to build a site, the templates are visually appealing, and you don’t need to concern yourself with scaling hosting for spikes in traffic. I have been reasonably happy with Squarespace, for starting out. Something that comes with the territory, however, is learning certain things about your preferred workflow. As you start to develop your blogging style, you are more likely to pick up on shortcomings in the tools at your disposal. As I get further into this, there are some examples for the way that I work – or rather the way that I wish to work – that are starting to get in the way.

The first, and probably the biggest annoyance, is I write in Markdown. While it is possible to use Markdown with Squarespace, the service only supports a very basic implementation, which means adding nice touches like fancy looking footnotes [1] requires both implementing awkward hacks, and converting your posts to HTML before adding them to the site. Both of which undermine one of the platforms major selling point – i.e., ease of use. Further awkwardness is encountered when working with images in your posts.

Squarespace has its own content delivery network (CDN), which for the most part is great, but in some cases it is another double edged sword. The CDN takes care of compression, and makes the media assets of your site load easily, regardless of where your audience is. However, working with Markdown or HTML on Squarespace you lose some of the benefits of those formats when working with images. Essentially, you have to leave the images out of your composition and load them separately, and the file management is by far the poorest feature of the platform. If you want to use the Squarespace editor and work with images in the manner that the platform is designed form, then it is great. Unfortunately, that doesn’t suit my workflow at all. What I am left with is a fiddly process of uploading images after the text, and dragging them into place. This might not sound too bad, but the reality is a degree of trial and error