Review: Wordpress vs. Squarespace for Beginning Writers

What I am: a tech enthusiast, Mac certified technician, and gadgeteer (I love gadgets and making up words).

What I'm not: a web developer. I have little experience with CSS, hosting, or backend server code (or code in general).

I know that most likely both types of people will read this article, and will attempt to make two separate recommendations.

Origin Story

Back in my college years I fooled around a good bit with Wordpress trying to make a website for a campus organization at Samford University I was leading back in 2010. While it was fun I easily burned a hundred hours tweaking, tuning, and twerking (I'm taking that word back, Miley) with plugins, widgets, and themes in what eventually led to one of the worst websites ever created. I can't link to it because it doesn't exist anymore. It died. It needed to die, it was awful.

However, when I decided to start around a month ago I decided to try Squarespace since I heard it financing all of the Internets: I wanted to try this new(er) guy on the block who was investing in the same things I was: Accidental Tech Podcast, The Talk Show, and all things Dan Benjamin over at 5by5

Ok enough background, here's my review:

Squarespace: the walled garden

Initial Cost: $0    Cost per month: $10

I was extremely happy with Squarespace for the first three weeks: sign up and setup was a breeze: I signed up and had a beautiful site running within fifteen. And it looked way better than anything I could ever do on Wordpress.

I didn't even know what I was looking for in a platform, I just wanted a place to write. Squarespace made that incredibly easy with built-in Markdown support, basic analytics with an option for Google Analytics support, and some way to post link-posts like John Gruber or Shawn Blanc.

Squarespace also had integrated hosting meant I didn't have to deal with an actual hosting company. ☚ Click that link for the exact feeling I had about not dealing with GoDaddy or some other sleaze-brained hosting company.

However the perfectionist tweaker inside me starting gnawing: Squarespace is great and all, but what if I could have more control.  Think of all the amazing SEO plugins and Twitter widgets I could use and themes I could use.

So I gave in to the OCD nerd inside and switch over to Wordpress. 

Wordpress: the 'open' platform

Initial Cost: $60 (for a great theme)    Cost per month: $20

First thing I had to do was get hosting, so I tried out Media Temple with their $20 a month Grid Hosting plan because I've seen their site listed . They were fantastic and I was up and running in no time. Their Wordpress installation was truly simple.

Now that I had my Wordpress site up, it was time to customize, customize, customize. I searched the web for the best Wordpress themes and landed on Enfold by, a beautiful theme that had the quality look and feel I was going for.

Good news: both Wordpress and Squarespace support importing and exporting to each other, meaning I could always switch back. Big thumbs up to both platforms for playing nice.

Importing my articles from Squarespace took three seconds and I had officially switched. One bad thing: it broke all of my previous permalinks and apparently the only way to fix it was to modify the .htaccess file: over my dead body. I got over it. No one was reading my site anyways (according to statistical data from Google Analytics, not false humility).

Because I knew my way around the Wordpress Admin page from earlier experience I knew where to find everything, but still it was overwhelming after using Squarespace's simple configuration pages. I was bombarded by ads to use Wordpress's Jetpack cloud features, articles starting feeding in the admin RSS block, two plugins that needed updating already, and a Wordpress update 😳.

After updating my plugins (which I didn't want or need) I started googling around to get the best plugins. Turns out they all are the best (if all are significant, none of them are). If you've done this before, you know that Googling 'Wordpress' leads you to a dark SEO ocean where every article has 'optimized SEO' and the best tips and maximized Google metadata. Gross. I didn't really need any plugins so I gave up.

Next was customizing the layout. I had to download Cyberduck and get it to work with my Media Temple FTP server (there goes another hour) and start tweaking with CSS, which ate up almost an entire day. Searching for how to tweak different CSS elements is another horrible experience ranging from "Here is every CSS modifier ever written with no explanation of how to use it" to "Oh just copy and paste this, you'll be fine". I wasn't fine. 

Many 'Wordpress tips and tricks' articles were written a few years ago and no longer apply to the newer versions of Wordpress or that particular implementation was broken with version 3.x of Wordpress. If I were John Siracusa I would go on a rant right now. (The whole experience was extremely similar to his rant on ATP about Minecraft mods, starts around 56:30)


The issue of support is a huge issue to me since I used to work for Apple: I need me some good support.

With Squarespace, if something happened to my blog or theme I could just talk to their support team about it. They have an easy-to-find support page with a knowledge base, customer forums, and an easy way to send a support ticket. Any question I had could be answered by a real human being: that's a big deal.

If something happened to my Wordpress blog or I couldn't figure out how to do some CSS trick with my theme, who do I contact? Now I'm dealing with three different entities that are in no ways integrated: a hosting company, Wordpress support, and the person who writes your themes: an unholy trinity of support.

Working with Wordpress brought on a lot of support fears: What if the author of my theme abandons the theme? What if a plugin I'm using is no longer supported by Wordpress? What if I get tired of this theme and wanted to use a different one?

The entire icky process starts over. No thanks.


There are endless possibilities with Wordpress and for me, as a beginning writer and non-developer, is it's biggest weakness. While the walled garden, Apple approach of Squarespace felt constricting at first, at least I felt safe in the garden. It was a cozy place that shielded me from my own ADD, tweaker tendencies and gave me a centralized support structure.

Wordpress felt like Android to me: it's openness means a great experience for those who love to tinker with their technology and a terrible experience for the everyman. It truly can do anything as long as you learn CSS, become a web-developer, and spend dozens (if not hundreds) of hours learning to do it well. 

The bottom line is that Wordpress took my focus away from writing and onto the 'platform'. One reason I love Apple so much is because the OS X and iOS platforms are designed to fade away and let you unleash your creativity without incessantly tuning their UI or kernel or backend code.

I believe this is what Squarespace is going for and it just works.


If you want an open, flexible platform that requires hundreds of hours to master (for the normal person), go with Wordpress.

If you want something that just works and lets you focus on your content more than the platform, Squarespace will put you at ease.