What’s Old is New Again (back on WordPress for the nth time)

I seem to have a problem: I can’t seem to make up my mind if I should blog or where the blog I can’t make up my mind to maintain should live. I started on WordPress. Then I switched to Squarespace. I got tired of the limitations in Squarespace then went back to WordPress.com. Then I got tired of the limits of WordPress.com and did a self-hosted install of WordPress running on a Digital Ocean droplet. Then at some point I got tired of having to maintain that myself and gave Squarespace a spin again and was thrilled with it. It had come a long way since the last time I had tried. But inevitably I got tired of the limits of Squarespace again and now I’m back on WordPress.com.

Don’t get me wrong, Squarespace is an amazing platform to keep a personal website and the pricing is phenomenally cheap for what they give you but I had three major issues with it:

  1. Their Markdown editor sucks.
  2. They no longer have an API for external publishing tools.
  3. Their idea of image handling is ridiculous.


It’s hard to describe just how poor of a Markdown implementation they have implemented. The editor is buggy beyond belief and it only handles bare bones Markdown. I was not the first one to request a more advanced flavor of Markdown, and I’m sure I won’t be the last, but the requests seem to have fallen on deaf ears because there has been no movement on that part of the tool in a long time. I write everything in Markdown and my preferred flavor is GFM (GitHub Help, or something similar like PHP Markdown Extra because I frequently use the extra items provided by those implementations like footnotes and tables.

Lack of API for publishing tools

I can see the reasoning behind ditching their old posting API because of the way Squarespace pages are built. Every page is usually made up of multiple blocks so that would make creating an external API pretty difficult. It wouldn’t be impossible of course…they could easily limit the API to publishing simple posts (as they seem to do with their own iOS tools) but they obviously think it isn’t worth the cost. I need the ability to post from other tools though and I want the ability to use automation tools like IFTTT with my website. That just isn’t an option with Squarespace right now and from the looks of it won’t be an option anytime soon.

Image handling

Squarespace can certainly afford to take a look at how WordPress (either self-hosted or on WordPress.com) handles a media library. Every image uploaded to WordPress is easily managed using their media library tools. Squarespace, by contrast, offers no such tools. When you attach images to a page or post they are essentially tied to that page and there is no central place to manage them. Want to get a list of every image asset on your site? Good luck with Squarespace because they don’t have a way to see that type of information.

If Squarespace fixes these things I might consider switching back again. Their pricing and feature set for most people is superior but they just have lousy support for the items that are the most important to me. I might have to dump more money into WordPress to get what I want but at least it is an open environment that has far more advanced management tools.

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