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 that can be frustrating. Dropping the images into the post splits up the text [2] in seperate blocks, which don’t always line up the way you want them to. Often I have to adjust the wording of the post to make the image sit right. Or I can use another workaround by inserting what Squarespace calls a spacer, but that results in excessive white space through the post. There is more, the Squarespace interface shifts your whole site top the right to accomodate its sidebar as you edit design elements. This may well be a by-product of the template that I use, but something to be aware of, you can get things looking the way you want them, only to have them move out of place again when you leave the style editor.

Delivering mixed content blog posts is one thing, and to date I have been willing to persevere with it, but the most vexing side-effect of that is the way it pushes me to do so much of my work for this site on my Mac. Don’t get me wron, I love working on the Mac, but these days I am doing more and more serious work on the iPad Pro, and I want to be able to manage the site on the go. Sure enough, Squarespace has an app for creating and managing your posts on an iPad, but it has some bothersome problems. First, the images problem is made worse by the fact that the app considers those mixed content posts to have complex layouts. If you edit posts that have images placed alongside or wrapped by text, it will collapse their layout so the images are at best inserted between paragraphs – the images are then increased in size to fit the margins. The app will warn you before doing this, but if it happens you have little choice but to return to the Mac. You can of course access the web editor on the iPad, but it is designed for precision use with a mouse, so you are asking for trouble trying to use it with a touch interface.

Unlike WordPress, there is no longer a posting API for Squarespace, meaning the only way you can use a third-party editor for composing your blog posts is cut and paste. This applies to working on macOS just as much as it does to iOS, but it provides nothing like the same degree of difficulty. Crafting a Workflow, or a similar process in Editorial or 1Writer on the iPad will allow you to manage the Markdown to HTML problem, but the app’s integration with the iOS share sheet is poor, so you are still left with cut and paste at the end of it – and that is before you get to the images. It is true that you can just simplify things, and working with simple layouts in the app does work well enough.

There are design elements on Squarespace that are dependant on the site template, but even when available might not work very well. The nature of The Appademic, as a site for bringing together tech and education, lends itself to link posts. I have separated them out from the main blog, as I’m not a big fan of sites dominated by link rolls [3]. Unfortunately, the template that I use doesn’t render block in a sensible way – there is no indentation, for example. This leaves me with another awkward workaround, among the bad options for this I have landed on adding a rich text block, but this adds yet more layout complexity – and to posts that should be the simplest of all.

I want to be clear, this is not a post bagging Squarespace. There is so much to like about the platform – both for functionality, and the company’s support of content creators more generally. For a lot of people, it is an obvious choice given how easy it is to use if you are happy to work as the platform wants you to. The visual design aspect is pleasing, one thing I have been very happy with is the way the site looks. It took no time at all to get everything setup. For photography sites, the CDN, and template the gallery designs make for one of the best experiences going around. This site, however, is not a photography blog. Neither is it a store front, another area that Squarespace excels in. Squarespace also gets a hard time about search engine optimisation, which I would urge you to take with a grain of salt due to the army of affiliate marketers working on WordPress selling would be bloggers on themes, plugins, and all manner of other snake oil to ‘make it rain’. The free source and extensible architecture of WordPress is its biggest strength, but it also opens it up to the current zeitgeist of internet sharks.

Having said that, I do have a genuine problem on Squarespace in that my use of Markdown and HTML seems to create errors in the data that Google and other search engines index [4]. If you are going to use the platform in the way it was designed – composing and posting with rich text, using a simple structure, and so on – you will not encounter the same problems. If you are an edge case for the way you work, like it appears I am with this site, it is worth considering how this might affect your discoverability [5]. The other side of that equation is that you are more likely to have readers stick around if they land on a slick looking site than if they find a dog’s breakfast on the end of those search results. Squarespace is not going to let you down in that regard. But more than that, Squarespace is in some sense a set and forget situation, you don’t have to concern yourself with more moving parts — there is hosting to manage, so you don’t have to deal a server. You don’t even have to go outside the platform for your domain management, everything is self contained within Squarespace. These are compelling selling points for the service. Again, be wary of affiliate marketers when choosing between WordPress and Squarespace, while WordPress is not difficult to use or to learn, it still takes time to master, and to my mind not only will Squarespace will get you up and running a lot quicker, but nobody is getting a cut to tell you that [6].

Why post any of this? Well, the workaround I mention above have created enough friction for me that I have made the decision to migrate to a self-hosted WordPress installation before the site gets too big to contemplate that. The main reason is the workflow, I need the flexibility that WordPress can offer for working with Markdown, and on iOS. If you have made it this far through this post, you can probably tell it hasn’t been an easy decision – even now I have my doubts. This site is paid in full for another six months on Squarespace, which is another reason to not take this decision lightly. As I have gone back and forth, reading innumerable frustrating and vapid articles, sifting through the noise of resellers, affiliates, hosting companies and self-appointed gurus, I have continually come back to the one thing that matters to me most in this, my ability to work in the way that I want to. Ultimately, The Appademic is a site about doing your best work – whether as an academic, a student, or any kind of creative nerd – and I feel it is bordering on disingenuous to be writing about that via a means that contradicts the message. I looked seriously at static engines, particularly Jekyll, which is not only a brilliant solution, but is perfectly adaptable for mobile use. Inevitably I settled on WordPress for the flexibility and better ability to eventually open out the site to other writers.

The Appademic will still operate as usual for the moment, as I clone it and test it elsewhere. However, any content going up in the next few days will be basic by necessity. There are bound to be mistakes, although I am working hard to mitigate them. If you happen to find any, please contact me to let me know. I will post an update on the other side to report on how it all went, but it should be obvious when the site design changes that the switch has been made.


  1. Such as this  ↩

  2. The Markdown blocks as the platform calls them  ↩

  3. There are notable exceptions, and they are not without their place  ↩

  4. You can address some of this by switching on Developer Mode to gain full access to the code, or using code injection hacks, but neither is an ideal solution  ↩

  5. Note, this is a contentious point too, there are plenty of people likely to say it won’t make a difference  ↩

  6. To be clear, this site uses affiliate links, in fact the only source of revenue – a very loosely applied term, as trust me this site runs at a loss by a long shot – is by way of links. However, not only is that is far from its reason to exist, but nothing is linked without personal experience and more often than not, considerable personal expense. I would hope the difference is pretty obvious. You can learn more on the disclaimer page  ↩