HeroPress: How Art School Led Me To Web Design

Here is Emily reading her own story aloud.

There are two, possibly conflicting, values inherent to my work and general enjoyment of life – collaboration and autonomy.

My background is in fine art. I studied painting in Chicago and New York in the mid-90s. I very much saw the web as another pliant artistic medium to work with, as well as a non-traditional way to show my artwork (since I didn’t have gallery representation). I created fun websites for myself, cropping my photographs for backgrounds and custom buttons, assembling content within tables, interviewing inanimate objects and making animated GIFs. And, yes, I did display an animated hit-counter and a “Built for Netscape Navigator” badge – if that helps you visualize this cacophony.

Living in capitalism, I was also governed by self-interest. I thought I might apply my creative abilities to the earning of a living wage since being a “professional artist” seemed to involve more social skills and luck than I could depend on.

Checking Out The Web

Aside from one class I took in college that covered HTML5 and Macromedia Director, I mostly taught myself by reading books by Lynda Weinman and Peachpit Press and building things. Learning HTML then, and later CSS, was powerful and a much more accessible entry point for a person like me – not especially technical but able to endure lots of trial and error to figure out how to make things work (eventually).

After graduating, I did not get a job at a prestigious design firm.

I was a terrible designer and I didn’t know how to dress or behave in a corporate environment. I probably still don’t. Instead, I waited tables and made websites for friends and fellow artists. After a few years of this, I started to wonder what I was doing with my life and whether I would ever be an artist myself. I volunteered to work with a small neighborhood arts group. I knew they needed a website, so I made one and later worked with a local web development company to migrate it to their proprietary CMS for our volunteer group. Finding I had an aptitude for coordinating people, creating content, and assembling something from nothing – being a web designer began to glimmer as a possibility in the back of my mind. I thought about pursuing arts administration but while at a nonprofit bootcamp had the epiphany that I needed to do my own art and not just support other artists. (Aside: This was to become the underlying struggle of my adult life, #WIP.)

Moving On

Back to waiting tables, I built a few more sites for friends who had started their own businesses. These early sites were all made with HTML, CSS, and a sprinkle of JavaScript. After a few projects, I began to realize that if I had to be the master of all content, I would quickly max out my capacity to take on new work. This was around 2010. I had recently met another web designer who lived near me in Chicago – Becky Davis. Becky also ran the Chicago WordPress MeetUp and, through her, I started my journey into WordPress theme development. I purchased “Digging into WordPress,” the non-official WordPress manual created by Chris Coyier and Jeff Starr. What could go wrong?

Learning a new technology came with its own challenges.

I landed my first non-friend client, hosted them on GoDaddy, and was almost immediately felled by some nefarious exploit. So, I figured out how to resuscitate a hacked site, I learned from bitter experience that I must always (always) have a backup, and I experimented with various commercial themes as I tried to figure out how to build a child theme in this new frontier of PHP code. It’s not as perilous for newbies now; hosts understand how to manage WordPress better and there is a ton of excellent documentation on how to do things (necessary for developing for the complexity and popularity of WordPress today).

Getting A “Real” Job

I worked on my own, slowly building up a business that supported me, but I felt that I was hitting a capacity ceiling again. This time, PHP programming was the biggest challenge. In 2015, I decided I was going to get a “real” job. My hope was that within a company, I would work directly with “real” programmers and develop my skills. I put “real” in quote marks because – people are just people, with flaws and failures like anyone else. Being a freelancer isn’t a “not real” job. There’s just pros and cons to each situation.

Also, even real programmers don’t understand semantic HTML or CSS.

The only designer on a very small team with remote developers, I was still working with clients and building websites with little direction. My work hadn’t really changed; I just had more pressure and no capacity to choose what projects I wanted to work on. I listened to lots of podcasts during this time – mainly Jeffrey Zeldman’s The Big Web Show, Jen Simmons’ The Web Ahead, Jason Ogle’s User Defenders – these inspired me with what was possible and what was important. I wasn’t finding this meaning in my day to day work however and that was a problem for me.

Back To My Roots

One day, walking back from the neighborhood grocery store, I saw a storefront for rent. It had high ceilings, big front windows and lots of wall space. Sure, the main view was a giant empty lot but this felt like an opportunity to reclaim some of that autonomy I was missing and maybe pursue my artwork again. I gave notice at my job and invested some of my savings into renting the commercial space.

From 2018 to 2022 I ran the storefront as a gallery showing emerging artists as well as my own work. I hosted artist talks, local musicians, and generally interfaced with the public. I also rebuilt my web design business in order to support this financially unprofitable venture. Though enjoyable, especially curating, I learned that running a gallery is also marketing, sales, writing, public speaking, and lots of people management.

So, I had effectively given myself two challenging jobs for the price of one with still less time to make my own art.

Although I wasn’t painting as much as I wanted to, in my web development work, I found that I had learned something working at a design firm with other developers after all. I no longer relied on commercial builder themes. I was coding custom themes with Underscores – albeit haltingly, with many Google searches. I started to follow more WordPress folks on the now extant Twitter, people like Aurooba Ahmed, Fränk Klein, Carolina Nymark, Nick Diego, Brian Coords, Birgit Pauli-Haack and many others. I was staying current on WordPress news and through the conversations online, felt more a part of a community than I ever had at my former job.

Refocusing

By March 2020, the pandemic mostly meant the gallery was closed. I couldn’t host public events. Without openings, there weren’t as many sales. Lots of neighborhood businesses closed. The vacant lot across the street that had promised to be a new apartment building remained a weedy lot with half-finished cement foundations and an increasingly elaborate display of graffiti. In 2022, the building I was renting space in was sold. I decided it was time to retrench. I went back to my home office and focused on web development work.

When Jonathan Bossenger tweeted that he was looking for a designer to provide a block theme that he could code up in a tutorial, I eagerly volunteered. It was still early days for block themes and they required a big mental shift from PHP development. A lot of traditional developers were unhappy and vocal about it. Although we didn’t complete the block theme project, it was exciting to connect with people in WordPress in other parts of the world and to feel that we were all invested in learning together. I’d like to try to build that theme at some point – I mean, I got the domain so I have to, right?

For a few years, I kept to a hybrid theme approach, adding theme.json to a custom Underscore theme.

I teetered on the edge of going for a pure block theme up until last year. Now, I believe it’s absolutely doable even for complex websites.

With block themes, I can now set aside the several, weighty PHP books I had intended to study, and remain a generalist. If my development / Googling time is reduced, I can explore other aspects of web design that are interesting and fulfilling to me – like content strategy and web accessibility.

Where I Go From Here

WordPress has enabled me to build a career for myself and to wholly determine my own path. It’s also, as self-employment options go, relatively profitable. The overhead is low, there’s a lot of avenues to follow a specific interest or stay broad, collaboration opportunities, and above all to keep learning (if you’re into that).

Web design and development in 2009 was different then it is in 2026.

I’m not sure I could do today what I was able to do 20 years ago as a mostly non-technical person.

Node, build processes, GitHub, tech bros, (not that those things are synonymous) are a little off-putting. The best way to learn is to do and, if there are too many prerequisites, you don’t.

But, WordPress is large and contains multitudes. The majority of people I’ve met through WordPress genuinely care about what they are building, why, and for whom. The open web is about inclusion, connection, and community – so, whether you are writing a blog post, contributing to a theme or plugin, or volunteering for WordPress in some way, everything we do matters. That cumulative effort is tangible and it’s a unique element of what WordPress is at its essence.