Lessons Learned the Hard Way: My Top 5 WordPress Fiascos

As developers, our mistakes evolve alongside our careers. This is especially true in WordPress development, where our blunders shift with our growing understanding of its codebase.

Matt Mullenweg once said (or something like it) that most people repeat their mistakes, smarter people learn from them, and the smartest learn from others’ errors. I like that, and I’d add that everyone makes mistakes, humble folks keep them quiet, but the bravest write them down and hit “publish”!

Enough philosophy, you’re here for a disaster story, and I’m your guide. So, buckle up as we revisit the five most cringeworthy moments of my WordPress journey.

Disaster #1: Updating a Hacked WordPress Core

Fresh out of shady CraigsList coding gigs, I landed a real agency job! Nervous and eager to prove myself, I was a staunch advocate for WordPress best practices, especially about never “hacking core.”

My first task was to resurrect a stalled project involving tricky WordPress login customizations. The previous developer, I was told, made progress by directly editing core wp-login files.

Knowing this was a no-go, I installed a backup/restore plugin and replaced the core with a fresh version. Confident I could replicate the existing features cleanly, I thought nothing of it.

Big mistake. My new boss was furious. She didn’t grasp the gravity of “hacking core,” and I lacked the composure to explain it. My only saving grace was promising a rollback using the backup plugin.

Plot twist: the plugin only backed up the wp-content folder. The core hacks? Gone. My email to her (since I was banished to my home office) still haunts me:

Guys, I can’t do the backup.

Despite my willingness to rebuild the features properly, she wasn’t having it. Fired, threatened with a lawsuit, and unpaid for two weeks of work, I was utterly humiliated.

The lesson? A backup is useless until tested and confirmed. But more crucially, it highlighted how to approach backups in WordPress, especially with the core.

I’ve grown to love managed environments like WP-Engine with their robust backup/restore systems. While other hosts have their tools, WP-Engine’s simplicity stands out. It’s fast, user-friendly, and even my clients can understand, monitor, and verify its use, unlike some obscure CLI command or Plesk setting. I’m a huge fan.

Disaster #2: The Great Platform Drag-and-Drop

New to both the professional world and Macs, I was adapting quickly, except for the “magic mouse.” Bluetooth hiccups led to accidental drag-and-drops, and my unfamiliarity with it didn’t help.

Back then, we used FTP for production deployments. I’d often spend days coding, chatting, and emailing, all with Cyberduck connected to production. Sounds reckless? It was.

One day, our entire platform vanished. Our sysadmin suspected a DDoS attack, and we developers, trusting his judgment, waited.

Hours turned into a full day, then two, with the platform still down. Finally, by the next morning, things were restored, and I was summoned by our CTO.

The culprit? My user, according to FTP logs, had moved the entire platform into a sibling directory. wp-content was now nested under wp-includes.

Mortified, I was met with unexpected understanding. Our CTO, seeing my remorse and potential, challenged me to prevent future disasters. This led to two key changes:

First, we found a CLI command to disable remote-to-remote file transfers in Cyberduck, a safety measure adopted company-wide.

Second, I delved into Git deployments. This culminated in a WordPress plugin integrating our Bitbucket versioning into the wp-admin update flow, practically eliminating our need for production FTP access. This plugin remains one of my proudest achievements. Today, Git proficiency is a given for developers.

Disaster #3: The Case of the Disappearing Content

Feeling confident in my WordPress skills, I received a seemingly simple task: add a “badge” to posts of a specific category. Scoffing at the idea of adding another conditional to the template file, I proudly implemented this filter:

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add_filter( 'the_content', 'myprefix_add_a_badge' );
function myprefix_add_a_badge( $content ) {

    global $post;

    if( ! has_category( 'sponsored', $post )  ) { return false; }

    $out = $content . myprefix_get_badge();

    return $out;

}

Spot the error? A quick staging test confirmed the badges were applied, so I deployed it to production and called it a day. The universe, as you might expect, had other plans.

Posts without the badge were rendering empty on the front end! The culprit? Instead of returning $content in the guard condition, I returned false. But this pointed to deeper issues.

Why didn’t I test that other posts remained unaffected? Why deploy so late in the day? Why was my quality control limited to clicking around?

The answer: lack of maturity. It took countless similar blunders to drive me towards tools like visual regression testing and unit tests. This specific mistake was a turning point, leading me to embrace phpUnit and xDebug. These tools, in turn, taught me about writing testable code, preventing more bugs than the tests themselves.

Disaster #4: The Infinite Loop of Doom

The task was simple: make the blog post byline display the date as “XYZ ago” instead of “10 November, 2011.” Unsure how, a quick Google search provided a working snippet. It was filled with math, especially division, nested loops, remainders, and rounding. But hey, it worked locally, so to production it went.

30 minutes later, a frantic Skype call from our sysadmin. Production was down, completely crashed. “Dividing by zero lately?” he asked, leaving me utterly clueless.

Here’s what happened: that “working” snippet, given a large enough dataset, had a nasty side effect. With certain combinations of days, hours, and minutes, its convoluted logic attempted to divide by zero. Remember high school math?

In ordinary arithmetic, the expression has no meaning, as there is no number which, when multiplied by 0, gives a (assuming a ≠ 0), and so division by zero is undefined. - Wikipedia

For computers, this usually means an error message. But in my case, it was catastrophic. The error messed with the loop logic, creating an infinite loop and a white screen of death. To make matters worse, each iteration logged the division-by-zero error, bloating the log file and crippling our file system. It was a self-inflicted DDoS attack.

The damage to a high-traffic site was bad, but the impact on my approach was invaluable. Ashamed of my blind implementation, I vowed to never again paste code without understanding it fully, even if it meant contacting the author.

More importantly, I committed to writing highly readable code, even for beginners. I became obsessed with WordPress coding standards, text editor extensions, inline comments, docblocks, even tabs versus spaces. I prioritized readability over ease of writing. This aversion to blind copy-pasting sparked a professional interest in managing third-party dependencies, fueling countless writing and speaking opportunities over the next decade.

The irony? WordPress core has a one-liner solution for this.

Disaster #5: The Project Management Black Hole

I landed a dream project as the technical lead and WordPress developer, overseeing an Amazon AWS Lambda developer and a JavaScript expert. With multiple people reporting to me for the first time, this was by far the most complex project I’d tackled. Calling it a “WordPress project” was an understatement, but WordPress was the central element.

Used to being strictly a technician and a minimalist at heart, I neglected implementing proper project management tools like Jira or Basecamp. The first iteration went smoothly, relying on a spec document and occasional Slack messages.

Everything changed when we started incorporating client feedback. Our seemingly manageable team felt overwhelmed. Responsibility, task status, even communication lines became muddled. We surpassed Gmail’s 100-reply limit multiple times!

Discomfort set in. The client felt a loss of control and visibility, while my Amazon developer suggested, “Maybe we should use Trello.”

Trello? For a three-person team? My minimalist instincts protested. But with the project already a mess, why not?

I meticulously combed through emails, spec documents, and scattered comments, mapping everything onto Trello boards. The project instantly revived. Communication became effortless, with clear task statuses and feedback integration. It was like regaining our sight after slowly going blind.

While the code still required effort, the project’s infrastructure allowed us to focus on the technical challenges. We could finally see clearly.

Thankfully, the project was completed to the client’s satisfaction. Today, I consider Trello or Jira essential for any team larger than one.

Embrace Mistakes, Learn From Others

A valuable lesson from my military days: “Lieutenants can make lieutenant mistakes, captains can make captain mistakes. What’s unacceptable is captains making lieutenant mistakes, or lieutenants making private ones.”

It’s okay to make mistakes typical of your experience level. What matters is your growth.

I hope we, as developers, offer each other the same compassion we’ve received when mistakes happen. May we remain curious and accountable in the face of our own errors, constantly innovating and learning from them. May we always have a supportive community of WordPress experts to guide us, sharing their experiences and preventing us from repeating their mistakes. And above all, I hope my own blunders, like the ones shared here, serve as valuable lessons for others.