WordPress vs. Squarespace

WordPress is the undisputed king of the CMS world, but Squarespace has a lot going for it: excellent UI (user interface), stability (no manual updates), excellent uptime (and transparency about it), full CSS control, very fair pricing, great add-on features including eCommerce, eMail list management, and scheduling. But the most interesting thing is that Squarespace is almost hack proof.

How we got to the age of the CMS:

I’ve been making websites since 1997 when Creating Killer Websites was the web designer’s bible. Everything was a hack back then. The age of Blogging officially started in 1999 when both LiveJournal and the original version of Blogger.com launched. This was the first time someone with no web design skills could easily place content online. Still, the idea of a client-editable website didn’t seem feasible until Macromedia Contribute was released at the end of 2002.

It wasn’t long before web designers who built websites without a CMS (content management system) were looked at skeptically. Web designers who built websites without a CMS were installing themselves as the gatekeepers of a website. After the CMS revolution, it was considered by some to be almost unethical for a web designer to insert themselves as a barrier between a client and a website. The thing is, popular CMS options (WordPress, Drupal, Joomla, Magento, etc.) are still quite technical. They are confusing and if you click the wrong thing, you can do serious damage. Many clients are happy to have an expert deal with the nuts and bolts of a website for them.

But what if there was a CMS that actually worked? A tool clients could use to make changes as easily as editing a Word document and to publish blog posts as easily as writing an email? Now that would really be something.

In 2021 we are well into the age of WordPress. But the thing about WordPress is that it is incomprehensible to most people. I get calls and emails from bright, tech-savvy people asking me to make very basic updates to their WordPress websites. Clearly WP isn’t the solution it's touted to be.

I’ve been on the hunt for a really good CMS since the early 2000s. I’ve even built a CMS from scratch with this focus: stability and simplicity first. My philosophy has always been to make the frequently performed tasks as simple and easy as possible. I’d rather have a client call me for complex changes rather than make the entire CMS so complex and confusing that they give up and rely on me for everything… like I’ve seen countless times with WordPress.

What WordPress Offers:

WP powers 60% of CMS-driven websites. I’ve dug deep into it several times. Every time I emerge completely unimpressed. It is ridiculously complicated, disorganized, and has never had a decent editor for clients. For web designers and developers, it's no picnic either. WP suffers from what I call “ship-in-a-bottle syndrome.” Every setting and piece of code is accessed through a tiny pop-up window. I have three monitors at my workstation, yet I have to peer into a little box that’s about 2% of my available screen to make CSS changes. Nevermind the fact that the CSS I need to edit could be located in any one of 4 or more locations. As someone who has spent 25 years with easy access and full control to the code of a site, working with WP is an infuriating waste of time.

What WordPress does provide is the ability to launch a complex website insanely fast. Spinning up a copy of WP is a single-click operation at most web hosts. From there you grab one of a million cheap themes, throw in a logo, a few plugins... and bang! You’ve got yourself a beautiful, modern, full-featured website! The vast number of very powerful plugins and excellent themes make WP incredibly alluring. A web designer can make a crazy-powerful website in less than a day. The problem is living with it.

WP sites require constant maintenance. There are DAILY security updates to deal with. PHP, WP, the themes, and all those plugins all require maintenance. Every time you login, you’re going to see that a handful of them require an update. The scary part is that any one of these updates could cause the entire house of cards to topple. And scarier still is that not running these updates virtually guarantees that your site will be hacked. The only solution seems to be to hire your developer to continually update and repair the website they sold you. I have to conclude that WordPress websites are not just unethical, but a scam.

In my opinion, the only way to justify WP is if you have an in-house expert. And I don’t mean an expert with the user-interface. I mean someone who understands the server, the database, and the PHP code in addition to being a web designer. Or, if your business model permits, go in with eyes open and understand that you will need to hire someone to maintain the site. Someone needs to run weekly updates 9at a minimum) and deal with the fallout of resulting incompatibilities for the life of the site.

Why Squarespace?

I was slow to embrace Squarespace because it is touted as a DIY solution. I have seen countless “code-free” web design tools over my career and they ALWAYS suck. The code these systems generate has tons of heavy, redundant garbage that performs poorly by every metric. I first took Squarespace for a test drive by making a few edits to a site for a client. I was impressed. Squarespace’s interface is super intuitive, well organized, and very very fast. It's almost like having a native application. The code it generates isn’t as clean as hand-written code, but it isn’t that bad and it’s well organized. A lot of this cleanliness has to do with what Squarespace accomplished in version 7.1.

Version 7.1

Now it wasn’t love at first sight. I’m working on my 5th Squarespace site as I write this (if you count sites I was hired to update). There is a learning curve to it. Some features are so transparent that they can be elusive. I spent quite a lot of time hunting for controls to adjust columns only to discover they don't exist. Column management happens automatically via drag-and-drop!

There are many web designers who have been using Squarespace for years. So I don't really have an opinion of the 7.0 and earlier versions. I know some features and controls have been lost, but the Squarespace team seems to be adding new features regularly and I haven't run into a problem that couldn't be fixed with a little CSS or JavaScript. But what has really impressed me is what they've done with code management in 7.1.

Separation of content and presentation:

All Squarespace 7.1 templates are essentially the same template. This is an epic move that few people appreciate. A basic principle of modern web design is the separation of content and presentation. The basic idea is that information should be stored as simply as possible so it can be displayed in multiple ways. HTML was conceived with this in mind. Text could be coded with headlines, links and paragraphs; but how it appeared would be up to the viewer and their browser settings.

Even in 2021, the raw HTML render of a web page should look like a simple text document. The design and layout is determined separately by the CSS (cascading style sheets). Colors, fonts, positioning, etc. are determined by the display requirements and design esthetics. Will the text be shown in 1 column or 4? Well, that depends on the size of the screen. This concept is one of the reasons responsive design is possible.

Making all “templates” essentially variations of one template is a crazy bold and powerful move by Squarespace. All the structural HTML differences that used to come with each template are gone. They now rely on CSS3 to do most of the actual design… which is frankly bad ass.

What Squarespace does well:


The user interface is by far the best I’ve seen for any CMS. It’s clean, well organized, and straight forward. Editing a page happens inside the page via a WYSIWYG interface. As options get more complex, there are some things that can be a little confusing, but it's really really good.

Stability, Uptime, and Transparency:

I’ve only used Squarespace for a year but I haven’t experienced any downtime. I’m also super impressed with their transparency about any issues that happen.

CSS Control:

I love me some CSS . It is crazy powerful, and crazy complex. I’ve been using CSS for almost 20 years and I learn something about it every week that blows my mind. With the clean 7.1 code structure and full CSS control, a designer that really knows CSS (and there aren’t that many) can accomplish almost anything.

Price and Features:

It’s quite a good deal. You can’t edit CSS until you get to their “Business Plan” for $216/year but it includes basic eCommerce. There are a ton of add-on features too like eMail marketing and scheduling that are impressive and reasonably priced.

The Downside of Squarespace:


There are some barriers in Squarespace. While CSS, custom code blocks, and code-injection let you get past some of the limitations, the results can be less than user friendly. (I try to avoid situations where my clients have to edit code). I’ve already documented a series of hacks to create what should be basic features. Still, Squarespace does seem to be adding new features frequently and my personal philosophy is to do the basics correctly and without headaches...which is exactly what they are doing.

You’re stuck in the walled garden:

Squarespace is a closed platform. You can’t see what’s going on inside the black box and there are lots of things you cannot tweak. This has repercussions for SEO and portability. Those who argue that WordPress is superior will make these points. A Squarespace site cannot simply be picked up and moved to a new host. Some search engine optimizers balk at the lack of access to the core code to really improve performance (which is becoming a bigger issue every day). Still, there are plenty of fundamental SEO tools available. If you really need complete control over the code and/or the ability to develop web applications, then Squarespace isn't for you.

Interestingly, Squarespace has made some impressive progress on portability. You can now import pages, blog posts, and perhaps more form a WordPress export.  You can also export your site to WordPress. These techniques won’t be perfect but they drastically reduce the labor involved compared to starting from scratch.

Also, remember that websites don't have an infinite lifespan. Planning to move a site to a new host seems silly. I’ve had sites that last for a decade, but that isn’t the norm. After 2-5 years, it's probably time for a redesign and a rethink of the content. So don’t sweat portability. It's a chance for a fresh start!


If you have more than 100 employees and a huge budget and/or an in-house team of developers, then you can do whatever you want and may not need to bother with managed systems like Squarespace. For most of the small businesses I work with, the benefits of Squarespace far outweigh the limitations. Squarespace is really impressive. It's stable, powerful, easy to use, customizable and affordable. For companies that don’t have a web agency on retainer, it’s definitely worth a look.

Web Design, CMS