Kris Black - designer, author, cartoonist, & illustrator


My Journal provides an overview into the work and creativity of being a designer, author, cartoonist, and illustrator.


Hello World! Rediscovering Squarespace

Squarespace Illustration by Kris Black

Squarespace Illustration by Kris Black

The title of this blog post is not original. It's a default title for a sample blog post used in a particular web publishing platform. I'll explain in more detail, but first, let me give you a little backstory.

The Backstory

From 2004 to 2018 I published my website,, using Squarespace. During that time I've had a specific career projection that has resulted in several key milestones. Many of which revolved around using Squarespace to build websites.

  • 1997—I began teaching myself how to design and code websites.
  • 2000—I graduated from college and started a career as a graphic designer.
  • 2004—I used Squarespace for the first time to make a website for myself.
  • 2006—I got my first paying freelance job designing an e-commerce website.
  • 2009 to 2011—I worked for Squarespace as a customer support specialist and continued doing freelance web design.
  • 2011—I left Squarespace and started building websites professionally for my day job. (See my LinkedIn profile for detailed career information.)
  • 2010 to 2013—I wrote two books about using Squarespace. -- Squarespace For Dummies (published March 2012) -- Squarespace 6 For Dummies (published August 2013)
  • 2012—I partnered with a colleague to start a small business, black&hue. We design and build Squarespace websites for creative professionals, entrepreneurs, and small businesses.

For the last 12 years, I've been hyper-focused on designing and building websites. While I love designing for the web, I want to change my focus to my first career love, illustration. For the next 12 years, I'm switching my non-day job focus to illustration.

The Future

I have a list of goals and actions to transition to a professional illustrator. It'll be a long journey as I build my new career but, most importantly, a portfolio of work.

One key factor in my success will be my website. Squarespace serves me very well, but earlier this year I thought it was time to move to another web publishing platform. This decision to switch from Squarespace to another solution wasn't an easy decision. As you read previously in this post, Squarespace has been at the center of my professional life for 14 years. Unfortunately, I thought that had to change.

Traditionally, Squarespace is a closed solution that offers only the functionality Squarespace, Inc. decides to put in their product. Don't get me wrong, Squarespace is not a terrible solution, but Squarespace's primary target audience is non-tech savvy users—ordinary people. Targetting these users means creating a product that works straight out of the box.

Enter WordPress

I'm not a typical website user. As a professional web designer and developer, I’ve grown accustomed to having total control building websites. I needed that level of access to building my new site.

From April 2018 until August 2018 I worked on my new website using WordPress. I bought a theme to customize and a fancy website building plugin that made it easier to customize WordPress.

After four months of building my new site, I was days away from my launch date. As I was wrapping up some content updates for the new site, I updated some plugins a core plugin I was using for my site, and things broke.

Like any good web developer, I had backups, and I was building my website in a locally hosted environment on my Mac. Reverting the plugin updates wasn’t hard, but I found my self in the exact place I was in early 2004 when I exclusively started using Squarespace.

Switching Back to Squarespace

My wife will be the first to tell you that I have a problem of always finding some way to distract myself. I like to think I pursue perfection before moving to the next step. Either way, I knew I made a mistake in trying to switch to WordPress.

I knew I didn’t want a website that required updating plugins, and troubleshooting compatibility issues between plugins. I didn't want the overhead of managing a local copy of my site and having to migrate updates and changes to my published site on a server. All these issues were the core reasons I choose Squarespace as my publishing platform in 2004.

While on a weekend vacation at the beach, I decided to keep my site on Squarespace. Starting that weekend, I set out updating my old Squarespace website with new content, pages, sections, and a refreshed design. After two weeks my site was complete and ready to launch.

Why "Hello World!" for this blog post title?

"Hello World!" is the title of a sample blog post automatically created when you set-up your WordPress site. It made sense to repurpose the title for a post about why I did not switch from Squarespace to WordPress.

I'll publish more details in subsequent posts about how I use Squarespace to promote and market my illustration. In the meantime, check out my portfolio work.