Alex Duner

The CMS Chronicles Part 1: The Trials and Tribulations of Using Squarespace

This is part one of a two part series about the Content Management Systems (CMS) I have experimented with during the first year of this blog’s existence. Part one deals with my short stint with WordPress and my longer, more complicated relationship with Squarespace. Part two, which will be posted later this week, covers my eventual discovery of Statamic, which I am currently using and loving.


When I first started writing here at alexduner.com I did what any aspiring blogger does and set up a WordPress install with a basic theme. I took advantage of the theme’s couple settings and changed some colors, installed a few plugins, and started writing. Shortly thereafter, the writing stopped.

There were two main problems I had with WordPress.

First, there was just too much friction between writing a post in Byword and publishing it. Second, I was not at all satisfied with the look and feel of my website. I wanted every aspect of my blog to be my own creation.

However, when I set about writing a WordPress theme from scratch, I was overwhelmed. There were so many resources that I didn’t know where to start. Whenever I tried to do something custom, it felt like any keystroke could break everything. I was lost in a jungle of code without a map or a compass and I had very little sense of what was going on.

A few months after initially getting started, I began thinking about moving to another CMS. I had been hearing about Squaresapce for a while on literally every podcast that I listened to 1 but it suffered from one of the same flaws as WordPress: I couldn’t own every pixel of my site.

That changed when Squarespace introduced it’s developer platform. The developer platform, which costs $20 a month, gives you the flexibility to control all of the CSS/HTML of your website.

After about a month of fiddling to get everything the way I wanted it to look, I took the site live and began posting a lot more frequently.

Squarespace has a (well deserved) reputation for providing great customer service. You don’t lug barrels of fuel up seventeen flights of stairs in the middle of a hurricane to keep your customers’ websites running if you don’t care about your users. That being said, at times I found the support system to be a bit of a black hole and some of my tickets and questions were never answered.

One of the biggest problems with Squarespace is its iOS apps. There is no nice way to put this: they are unusable. David Charier wrote about this problem in September of 2012:

The iOS apps have floated in various states of broken limbo since I started using the platform, but for a while I gave them a pass because I hopped onto testing the iOS 6 betas pretty quickly. Then more and more users started telling me they’ve been like that for three years. For example: if you create a new post from the iPhone app, it assigns a randomized slug like /AUYQKEKyIUIqYUU, and there’s no way to edit that from the app. The iPad app still isn’t retina, and while I’ll grant iOS 6 has only been public for a couple weeks, none of its buttons are wired up to actually do anything; it is literally broken.

It still hasn’t been fixed. If you edit a post, Squarespace changes its timestamp; fixing a typo on a day old blog post carried the risk of messing up the entire order of my posts. That’s unacceptable.

There were a other minor things missing from Squarespace too, like an API and MultiMarkdown support, which were not deal breakers by themselves, but when combined, add up to a lot of frustration.

In the last two days alone I have seen three people complaining about the Markdown block because the cursor sometimes gets three or four characters behind where you are typing, which makes it impossible to copy, paste, or generally edit anything.

Squarespace’s feature set is truly amazing. If you want to build a store, Squarespace lets you do that. If you want a nice commenting system, Squarespace lets you do that. If you want to host a podcast, Squarespace lets you do that too.

But what I wanted to do was write and I don’t care how nice all of your other features are if the cursor doesn’t work.

The final straw for me was the lock-in that I felt using Squarespace. Just like with WordPress my data was all stored in some database somewhere and unlike WordPress even if I learned SQL, I still had no way to access it. The export feature that Squarespace has only works with WordPress and gives you this really ugly XML file that is unusable with almost any other CMS without heavy modification. I wanted out sooner rather than later so that any conversion would be as easy as possible. Squarespace gave me control over the look and feel of my website but it didn’t give me control over my content.

Squarespace is a fantastic company that creates a fantastic product which I’d recommend to anyone with little to no technical expertise looking to create a well designed website. It’s a great CMS, just not for writing. It wasn’t the right solution for me.


  1. I’m pretty sure that Squarespace singlehandedly keeps the tech-podcast industry afloat. I shudder to think about what would happen to my favorite shows if Squarespace stopped sponsoring them.