WordPress Vs Squarespace: A Guide for Creative Entrepreneurs

WordPress or Squarespace is an ongoing question. Unlike a trending topic, this one has taken up residence on the internet. I’m pretty sure there is a debate happening online at any given time in the 24-hour cycle over these two platforms.

For creative entrepreneurs, WordPress and Squarespace are the two leading choices for a website.

Naturally, this is one of the first decisions when thinking about a website.

As a Squarespace Web Designer, I might seem bias. I’m not.

Squarespace will not work for everyone.

Before I discovered Squarespace and started offering websites to female creative entrepreneurs, I built websites on Wordpress.

Each platform has its merits, so the question really isn’t whether or not Squarespace is better than Wordpress.

A good place to start would be determining what are your business needs are. Follow that up with asking yourself what are your business goals and figuring out what you need from your website.

Answering these questions will help you figure out if Wordpress is best for you or if Squarespace just cannot be beaten!

To help you decide which platform is best for you, this post dives deep into both. It provides enough information so you can compare and contrast.

Table of Contents

What is WordPress.png

What is WordPress

WordPress started out as a tool for bloggers. As blogging became popular, several companies created sites that allowed individuals to share words, photos, and graphics - content. Many of these companies charged for this service. WordPress was free.

In addition to its low cost, WordPress offered a major feature. With a few tweaks, WordPress could be expanded beyond a blog into a full website. And it was still free.

WordPress grew from being a simple blog to a Content Management System - software that is used to create and manage content. Sure, there was the WordPress branding in the domain name - the address of your website, but this didn’t diminish its draw.

In fact, since at its heart WordPress is a blog, it could look like a website but still function as a blog. Unlike a website that remains fairly stagnant after being built, a blog is updated regularly.

Regular updates in the form of a blog post increase the chances of being noticed by search engines like Google.

Strip away the themes and plugins from WordPress and basically, you have a blog.

If your primary goal with your new site is to blog, WordPress may seem like the obvious choice, initially. While WordPress is a robust blogging platform, it comes with a steep learning curve.

Additionally, you will have to decide if you want to start with one version of WordPress over the other.  

Wait! What?

Let me explain. WordPress comes in two forms - WordPress.com and WordPress.org. WordPress.com is hosted on WordPress by WordPress. This version does not offer customization and creative freedom.


When individuals suggest WordPress because of the flexibility and creativity offered, it is WordPress.org they are talking about. When the differences between Squarespace and WordPress are being discussed, people compare WordPress.org to Squarespace, usually.

WordPress.org is free version but, and this is a big “but,” you will have to get a host - a service that houses your site, and a developer - someone to install, build out, and maintain your site. WordPress suddenly becomes expensive, fast. It is also time-consuming since you will have to find a reliable developer to turnaround your site.

Once the site is up and running, you will need to keep the developer on a retainer. WordPress requires regular, and in some cases, daily maintenance. This is something that really cannot be skipped.

In addition to regular maintenance that keeps your site up and running, you will need to do this to also keep your site secure. WordPress can be hacked, easily.

Remember above I mentioned WordPress.org is free? It is free because it is an Open Source software. This means that the source code - the programming that makes WordPress work and run - is open to anyone.





Anyone with the technical skills can look under the hood of WordPress and make their own changes to it, which is great when individuals are interested in making the software better but bad when there are less than positive intentions at play, like hacking.

It isn’t just the WordPress software itself that is vulnerable to attacks either. All the plugins - additional software installed to expand a WordPress site and make it more robust, they ultimately open the door to hacks.

If there isn’t any time to run through your site daily to ensure plugins are working properly, your site becomes vulnerable. Having someone available or having the skill set yourself is essential to the safety and security of your site, and more importantly, your brand.

If this all sounds really complicated, you are on the right track. There’s a reason for this, too! WordPress was never intended for individuals without a technical background. This is why it can be a really complicated piece of software to learn and use.

Individuals who work on WordPress sites usually have the following skills:


  • CSS

  • JavaScript

  • PHP

  • Domains

  • Hosting

  • FTP

  • Git + GitHub

  • Responsive Typography

  • Flexbox

  • Media Queries

  • And more...

Why Choose WordPress

People love WordPress, and they choose it for a few reasons:

Limitless Customization

WordPress makes it possible to create a website that is very unique. While WordPress offers themes - templates, essentially - these themes can be modified without many limits, if any at all. This creates the possibility of having all of the needs of your site met.

Capabilities Extended

WordPress uses something called plugins - pieces of software that can be installed to expand the functionality of a site. These plugins cover everything from improving a sites SEO - search engine optimization, eCommerce, and spam blockers - to name a few.


The WordPress software itself is free. There aren’t any monthly fees from WordPress.org to use it. There are other costs associated but, WordPress is free to use. Upgrades to WordPress are often free and some plugins that improve the functionality of a site are sometimes free, too!

WordPress is used by large companies all over the world. Media brands especially took to its robust content management capabilities. It is the choice of sites people use daily such as, The New Yorker, Tech Crunch, and MTV News. And bloggers love it, too!

Professional bloggers and content creators often choose WordPress as the home for their business. It is considered the go-to for both bloggers and content creators.

Many did not start off using WordPress because of its considerable investment. In the world of creative entrepreneurship, anyone looking for a site to share their content will often be told to go with WordPress.

Going with WordPress can seem like a dream solution. There are downsides to note. For some, the downsides are enough reason to choose Squarespace over WordPress.

Earlier I mentioned that I built my first websites on WordPress. At the time I needed a website for a project and there was no budget. What I did have in lieu of a budget were some coding and design skills so, I took on WordPress.

It was super frustrating. From my experience, I can offer some of the cons of WordPress.

No One To Call For Help

When I ran into an issue, problem, or simply had a question my only source was the forums. Because I was new to WordPress, I did not know the lingo and couldn’t always phrase my question in a way that generated the right search results.

As you’ve probably already guessed, this led to more stress and frustration, lol! Fixing a problem took a lot of time, and while I didn’t always have the time to focus on one problem, I did not have a choice; I had to invest the time to fix problems myself.


I’ve mentioned before that WordPress requires regular maintenance. This is non-negotiable because without the maintenance your site will either not work properly or will be exposed to security breaches.

With WordPress it’s good practice to look at your backend - the guts of your site, the area site visitors do not see - every day to make sure that everything is updated and running properly.

Plugins will often update or go out of date. This is important because an out of date plugin or plugin not updated is a way into your site for a hacker or some other security concern.

More often than not you will be notified of this, and unlike the updates on your iPhone, you’ll want to respond to these right away.


Since WordPress is chosen because of its expansive qualities, thanks to plugins, it’s worth delving deeper into this aspect. Earlier I mentioned that WordPress is Open Source so, in addition to anyone being able to look under the hood of the software, anyone can create a plugin.

There is little to no standardization with WordPress so, when someone creates a plugin it does not mean that it is compatible with other plugins. Plugins are installed at one’s own risk and their compatibility is really through trial and error.

Who has time for this!

Technical Skills

As you can imagine at this point, having some tech skills might be useful. You are 100% correct in this.

With WordPress, you will want some knowledge, even if you do hire someone to take care of your site. Being able to communicate effectively will save time as well as take the stress and frustration out of situations.


I’m just going to give it to you straight: There is misinformation about the cost-effectiveness of WordPress.

Yes, WordPress is free to download, use and install, but your domain name and hosting are not free, and this is just the beginning.

If you want your site to look and function a certain way, you will need to hire a developer. This costs money. The cost of an experienced, professional developer often starts at $10,000.

If you are not working with a large budget right now, you may be tempted to find a developer on a freelance website.

This is not recommended, nor is it a viable solution. Talk to friends or other creative entrepreneurs for referrals for a developer.

Your site is very important since it is the 24/7/365 face of your brand. You don’t want to leave this important task to someone who cannot be verified. Even still, things happen.

For a while, I put my WordPress skills to use and helped out on two sites. One site was for a professional coach and the other was for a non-profit.

The site for the life coach had a developer, but additional help was needed because he was not very responsive. It would take about two months or more for him to respond to basic requests.

Since he started building the site two years ago, it wasn’t ideal to start all over again with a new developer. Yes, the “new” site was under construction for two years and was still far from launching.

The nonprofit’s website on WordPress wasn’t in a better situation. While their site was done, no one was able to make improvements or upgrades to the site after the developer quit. This wasn’t due to anyone lack of knowledge of WordPress.

The developer intentionally made the site overcomplicated through the code in order to create job security. When he left the nonprofit he took all of his knowledge of the site with him. The nonprofit had no choice but to start all over again with a new site.

The developer you choose to design and create your WordPress site is exceptionally important. So, even if you have a large budget for your site and can find a reputable developer, having some tech skills when it comes to WordPress is still important.

Is WordPress Right For Me?

To recap, WordPress has its pros and its cons, such as:


Fully customizable

More themes/templates to choose from

Learn new skills


Steep learning curve

Knowledge of coding needed

Costly to start and run


Security issues

Seeking and securing reputable help


What is Squarespace

Initially, Squarespace began as a place for photographers and other creatives to make a portfolio. Squarespace also catered to bloggers.

These were two of the options available: make a portfolio site or start a blog. Squarespace made it easy to create either one. Without knowledge of code, one could create a rather chic blog or creative portfolio.

One could say that since the beginning, blogging has been top of mind for Squarespace. Over the years different versions of Squarespace have been released.

With each version, Squarespace has offered more possibilities to more people, but blogging still remains a robust feature offered.

Through each version, Squarespace has expanded upon its capabilities making more possible without the need for a lot of technical skills.

Currently, there are greater possibilities for entrepreneurs and small businesses, particularly creative entrepreneurs. Newer versions of Squarespace have the creative entrepreneur in mind.

In its essence, Squarespace is a website building platform meant for individuals with little to no technical knowledge. With a little bit of time, anyone can successfully use the platform.

With Squarespace, it is easy to create a clean, modern website thanks to their selection of gorgeous websites and a relatively low barrier to entry.

Squarespace is available as a monthly membership or as an annual membership. Included in the price is the use of their templates, hosting of your site, 24/7 customer service, and several helpful integrations.

Integrations are kind of like Squarespace’s version of a plugin, and basically, it is software that can connect with your Squarespace website to expand its capabilities and functionalities.

Unlike WordPress, there are fewer security issues with integrations than there are with plugins, and you do not have to maintain integrations yourself.

Why Choose Squarespace

Like WordPress, Squarespace has its fans. Squarespace is often the choice for creative entrepreneurs.

Even well-known bloggers choose to use Squarespace, and there is a good reason for this. Take a look below to see why small businesses, especially creative entrepreneurs choose Squarespace.

Easy to Use

With Squarespace, you do not have to download or install anything. There’s no need to look for a hosting service or pay for one either.

Squarespace is what is called a fully managed platform, which means they take care of everything for you!

Clean, Modern Mobile Responsive Templates

Squarespace offers many templates to choose from but each one is created with modern website trends in mind.

Outdated concepts are not part of the design. This includes acknowledging mobile users.

All of Squarespace’s templates are responsive. This means that it won’t matter if your clients or customers are viewing your site on a laptop, tablet, or their mobile phone; your website will look great regardless of the screen it is being viewed from.

Customer Support

This one is huuuge! The customer service. Real people are available 24/7 to answer your questions and point you in the right direction if you get lost. Support is available via email and live chat.

One of the features of the live chat that I love is being able to get a transcript of the conversation emailed to me so I can have it for reference.

The support team at Squarespace is stellar, but they also offer an online knowledge base with articles that are updated regularly and often, so no outdated material that leads to nowhere.

There are also quick video tutorials to help you out.


Squarespace offers their versions of plugins which are already built-in. You won’t have to worry about ensuring different pieces of software you would like to use in order to enhance your site are compatible.

Instead of offering plugins that can threaten the use and functionality of your site, Squarespace simply incorporated helpful software so you don’t have to think or worry about it.

To get more out of your site though, Squarespace has partnered with other reliable companies to offer integrations.

This means the software that has been tested and determined to be compatible with Squarespace is made available to you at no additional cost.

Integrations with MailChimp email marketing and Acuity scheduling are including with your membership fee.


Squarespace has simple, straightforward pricing. It is clear and easy to understand what is included at each membership level.

Currently, they have a total of four options. If paying annually, prices start at just $12 per month. And this price includes your site, hosting, support, integrations, and more.

As a Squarespace Circle member, I am pleased to offer my clients 20% off their first year of service with Squarespace.

That’s a nice saving that can be put towards travel, art supplies, or crystals, just saying!

Inclusive Service

It’s worth nothing that, advanced website maintenance is included in the subscription fees for Squarespace.

Yup, that means not having to find a reputable developer to have on call because Squarespace has their own developers on staff to fix anything buggy or security related. If an issue arises, Squarespace handles it!

No muss, no fuss.

Squarespace offers a pretty sweet deal to creative entrepreneurs looking for a web presence. It seems like a done deal to choose Squarespace as the online home for your business.

Of course, I would be remiss if I didn’t mention some of the drawbacks of Squarespace.

Below is a list a few common concerns and complaints about Squarespace.

Limited capabilities/templates

Squarespace offers several templates to choose from, and they are designed with different needs in mind such as online store, portfolio, or blog.

The main goal is to prioritize the intention behind a website so, many of the template’s capabilities are focused on achieving said intention, whether it offers your customers an easy to use shopping experience or a beautiful portfolio site to show off.

The templates on offer to its customers are geared toward the creative entrepreneur, however; some may find that the templates available do not allow enough creative control.

Another drawback is the workarounds needed in order to create a large store on Squarespace.

Each product page is limited to 200 products. If you own a boutique shop with a limited line, this will not be a problem for you, but it is definitely something to keep in mind.


Not everyone agrees on Squarespace’s SEO capabilities.

SEO is an acronym for Search Engine Optimization or the set of methods and tools used to make your site appear in search results generated on Google or Bing.

Much of Squarespace’s SEO is built-in whereas WordPress will utilize plugins.

The truth about SEO is that sites like Google, Bing, and Yahoo play their cards close to their chest when it comes to discovering what actually improves one’s search results.

In fact, each site regards the recipe to top search results a very closely guarded secret. Still, many are under the impression that WordPress is superior to Squarespace when it comes to this aspect.

WordPress is Open Source and Squarespace is fully managed so, Squarespace has a team of people who work solely on SEO. I’ll let you be the judge on this one ;).

Let’s recap: Squarespace is a one-stop shop where your website and hosting is in one place. Because of this, much of the routine maintenance is done for you.

This can make your need of retaining someone to take care of this for you unnecessary. Squarespace is easier to learn, but if it’s not your thing, or you want greater customization from your template, you can hire a Squarespace web designer who will give you the site you want and show you how to use it!

Is Squarespace Right for Me?


Easy to use

Many integrations

Less maintenance

Small business, solopreneur, and creative entrepreneur friendly

Either you or a Squarespace Web Designer can help you customize

Better security


Limited templates

Less customization

Is Squarespace Better Than WordPress?

You have a tough decision ahead of you but, it’s certainly not impossible.

Hopefully, this post has helped you sort through some of the questions in your mind and provided some advice based on some experience.

Some things to keep in mind about choosing Squarespace or WordPress is that ultimately your website needs to be capable.

It needs to support the functionality you need.

Your website is an incredible ally in your business, and for you, it just might be your business - the place where you showcase your products or services, where you meet customers and clients, and the face as well as the personality of your brand.

It’s worth it to ensure that your site can meet these needs.

Squarespace serves new and mid-level businesses and creative entrepreneurs quite well.

If you are running your business yourself and collaborate with others to make it all possible, then Squarespace might just be your unstoppable business partner.

For us solopreneurs out there, having all the right tools on our side certainly make it feel like doors are opening for us and we’re in the right flow.

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