WordPress – The Eras Tour (Taylor’s Version)

WordPress turns 20 in just a few days. I’m proud to have been contributing to Core for 13 of those years and being a part of the community for an additional 3. I learned WordPress in large part by coding under trees and in 24-hour coffee shops. During that time I didn’t listen to Taylor Swift, but that would change.

This summer, Taylor Swift is performing on her Eras tour. She’s playing some hits and deep cuts from each of her eras. While Taylor hasn’t been in the public eye for 20 years yet, if we look at each of her albums/eras we can find some commonalities with WordPress. So what do each of the WordPress eras look like? Let’s look at it from the lens of Taylor Swift.


In Debut, Taylor is introduced to the world. The first song, “Tim McGraw” is described by Pitchfork in its 2019 review as “…a saudade-drenched mid-tempo ballad that’s as much a love letter to music’s power as it is to a soon-to-be-ex-boyfriend leaving for college.” She was 16 at the time and a recent transplant to Nashville making country music but with hints of the pop star she would become. Similarly, When WordPress made its debut, it could only hint at what would become. The first version of WordPress featured hits like “Texturize — So good it’ll make your quotes curl”.

WordPress 0.71 immediately followed with enhancements like Post Statuses. These early releases had a small team with folks like Matt Mullenweg, Mike Little, Dougal, Alex King, and eventually Ryan Boren. But they laid the groundwork for the WordPress we would use today.

At this point, WordPress was a blog engine and for many a hobby project. The web in 2003-2005 was a different place and this era of WordPress was different than the one we have today. Instead of Plugins, Blocks, and Themes, WordPress had my-hacks.php. WordPress 1.2 brought the initial plugin system and 1.5 the theme system which saw this era come to a close. Imaging WordPress without Themes is like imaging Taylor without Love Story but both had their times.


The only thing better than Jazz is Taylor Swift.

Matt Mullenweg (As said by ChatGPT in an AI interview where I told it to say this)

The Fearless Era is where Taylor Rolling Stone’s review makes it clear that Fearless“…sets its starkly honest descriptions of love-crushed vertigo (“Abigail gave everything she had to a boy/Who changed his mind/And we both cried”) to thrilling pop anthems that effortlessly fuse styles while sounding natural as if Swift is her own genre.” If Debut is where WordPress and Taylor Swift made their introduction to the world, Fearless is where they grew up and defined themselves.

As with all growing times, The Fearless era is one that featured missteps and mistakes both by Taylor and around Taylor. This is the era of the infamous interruption at the Video Music Awards by noted anti-semite Kanye West. In this Era of WordPress, mistakes such as the quickly reversed articles fundraising debacle were just as present as victories like the first WordCamp and the first visual editor. For Taylor and WordPress, this was a growing, learning, and succeeding era.

Speak Now

I first made Speak Now, completely self-written, between the ages of 18 and 20. The songs that came from this time in my life were marked by their brutal honesty, unfiltered diaristic confessions, and wild wistfulness

Taylor Swift

Speak Now is a story of growing up and a story of imperfections which I think is a great analogy too much of the roughly 2.1 to 2.9 era of WordPress. This is when WordPress started to become more of a Community project. WordCamps went from 1 in 2006 to 7 in 2007 to 25 in 2008. This is the era that started to see Lead Developers like Mark Jaquith, Andrew Ozz, and Peter Westwood join Ryan and Matt in really driving WordPress forward.

This era also had the biggest redesign in the WordPress Admin. Growing up and imperfections often involve making mistakes and the Happy Cog redesign introduced in WordPress 2.5 included enhancements but it also lead to WordPress canceling the 2.4 release and was followed up very quickly by Project Crazyhorse and WordPress 2.7 which laid the foundation for the UX and most of the UI of the WordPress dashboard for years (and eras) to come.


Red is when Taylor went from country pop starlet to one of the biggest stars in all of music. It took good and made it great. The addition of custom post types, the “Big Merge” of WPMU and WordPress, and the Admin Bar similarly helped WordPress go from good to great.

This is the era when WordPress’s market share started growing at the rate of a Drupal or a Joomla a year (or more). At a time when open-source content management systems were getting more and more attention, WordPress took first place and hasn’t released its hold on the market.

WordPress currently lacks it’s own “All Too Well (10 Minute Version) (Taylor’s Version)” but perhaps the command center being in the admin bar would be this?


1989 and Reputation built on Red’s pure pop success and brought continued success and some of Taylor’s most recognizable hits. Instead of one number-one hit on the album, 1989 saw Taylor deliver banger after banger. The “Release Lead era” of WordPress from 3.6 through 4.9 saw banger after banger for WordPress. Features that had been relegated to SAAS could be included in your installation of WordPress out of the box.

In many ways, this was the cementing success era for both Taylor and WordPress. For WordPress, this meant evolving features such as updating plugin/theme updates to be inline or automatic instead of requiring page refreshes. WordPress did innovate with things like the addition of the REST API, but its user features were mostly about making things better.


WordPress logo on Taylor Swift Lover background

Taylor Swift’s “Lover Era” was a time of critical and commercial success. Lover is sonically diverse, and its maturity, honesty, and catchy melodies earned praise such as The New York Times calling it “a transitional album designed to close one, particularly bruised chapter and suggest ways to move forward — or in some cases, to return to how things once were” It’s not without controversy though as Swift was criticized for beginning her political activism. While other musicians such as Kid Rock supported the fascism that was on the rise, Taylor released “You Need to Calm Down” in support of the LGBTQ+ community.

Gutenberg is similarly controversial. While some haters gonna hate, hate, hate, hate, its inclusion in WordPress 5.0 included a very vocal minority sprouting that WordPress would end due to the change. Instead, this era saw WordPress continue its growth.

The release of Gutenberg also served as a close to the release lead era with Matt stepping back in to lead multiple releases in a row. Like Taylor returning to positive pop after Reputation, Gutenberg returned WordPress to revolutionary rather than evolutionary changes.


WordPress logo over a black and white forest like Tatylor Swift's Folklore's cover.

This pair of albums came at the heart of the Covid-19 Pandemic. They were surprise releases, but not surprise hits. These albums were less about individual hits and more about being sonic adventures you could enjoy with a glass of whisky, a box of tissues, and a longing for something else.

During the Pandemic, WordPress released block-based themes. Unlike Taylor’s albums, this was not a surprise release having been talked about for years in advance. These themes are more flexible and customizable, and they make it easier to create a unique and engaging website. As a result, they are becoming increasingly popular with WordPress users but learning them might require a glass of whisky, a box of tissues, and perhaps some longing for a different time. 

Midnights and (Taylor’s Version)

This leads us to now. Taylor is re-releasing her old albums and embarking on an extremely successful tour. WordPress re-released the widgets screen and the customizer but is calling it Full Site Editing now.

Each Taylor’s Version release and each WordPress release continue to show that they are still bejeweled and can still make the whole place shimmer.

If I have my way, in another twenty years, both WordPress and Taylor Swift will continue to be leading the way for the world. And perhaps one day around the time of WordPress 15.0 there will be a release named after Taylor Swift.

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