How did a business teacher end up in WordPress support? Hallway Chats 106

How does a business education teacher end up in tech support, answering plugin tickets during nap time? That’s the story I told Tara Claeys and Liam Dempsey on Hallway Chats, a show where people who use WordPress share how they got there. I was the guest on episode 106.

🎙️ Episode details

• Show: Hallway Chats, episode 106
• Hosts: Tara Claeys and Liam Dempsey
• Guest: me, then credited as Courtney Robertson with my old site, CourtneyEngle.com
• Released: July 4, 2019
• Topics: teaching WordPress in high school, tech support for The Events Calendar, and balancing work with family
• Listen and read along: Hallway Chats episode 106 with the audio and a full transcript

🏫 From the computer lab to the classroom

I told the hosts I spent about six years teaching high school business education, which meant computer programming, before running my own web agency for about eight years. My college coding class still makes me laugh: notes on paper, then a walk to the lab, a disk, PICO or vi, and telnet. I decided I wanted to teach students a better way.

Later, covering for a teacher friend at a technical high school, I taught WordPress without calling it that. The pitch to the school was PHP, JavaScript, basic server maintenance and running a content management system. WordPress happened to cover all of it.

🧰 How do you teach something as big as WordPress?

Liam asked how I built a program around a topic that wide. My answer was a sequence. Students installed WordPress locally first, with a DesktopServer license donated to the class. Then they learned to be good users: posts, pages, custom post types and default themes.

After that came a child theme, starting with something as small as heading colors, and finally a bare Hello Dolly style plugin. I ran the class on LearnDash, which also served as my grade book, and recorded my SMART Board lessons as screencasts so students could work from home.

The school’s computers reset themselves on every reboot, which made a local install exciting in the wrong way. (Yes, that went exactly as expected.)

🎫 What did tech support teach me?

At the time I worked part time on the support team for The Events Calendar, about 15 to 20 hours a week. Support work fit a schedule built around two toddlers, because I could clock in, answer tickets and step away when my kids needed me.

I was also growing into managing the knowledge base, which had more than 260 articles. Gutenberg had arrived, so every feature needed screenshots and videos for both the classic editor and the block editor. That job pulled on my teacher mindset: explain the task at the reader’s level, so they don’t have to wait for a reply.

⚖️ Balancing tech support work and family

Tara asked how I balanced work and family. I said I had narrowed what I take on. Technology tempts me to help with everything, so I asked what was manageable for that season, given my priorities, and where I wanted to grow next.

🧪 What can you take from this tech support story?

• Educators: teach WordPress as a vehicle for standards you already cover, such as PHP, servers and content management.
• Tech support teams: treat the knowledge base as teaching. Every article answered once saves a ticket later.
• Anyone returning to work: a scoped, flexible role can keep your skills current while life is full.

📝 What I wrote when I first shared this

I first posted about this episode on March 4, 2021, nearly two years after it aired:

Did you know that I used to work in WordPress tech support release communications? It was the perfect job while juggling 2 babies that were less than 15 months apart. I learned so much in my time at The Events Calendar about the inner-workings of a WordPress products company. I grew in my understanding of the workforce and also in my interpersonal skills. Thanks Liam and Tara for having me on Hallway Chats to share about it.

Also, more conversations like this one live in my podcast and speaking archive.

🗓️ Archival note

This episode was released July 4, 2019. On November 9, 2026, I moved this post to that date (it was dated March 4, 2021) and rebuilt it from the publisher’s episode page and transcript. I kept my original 2021 note above and removed later generic paragraphs that didn’t come from the episode. I reviewed the transcript, not the audio.