Reflections on My 2 Weeks Writing for The Tavern

As my 2 weeks as a guest writer at The Tavern wind down, I thought y’all might be curious to hear some of my reflections on the experience.

As James wrote, bringing 7 writers in for 2-week stints is kind of like The Hunger Games – many go in, two get the job.

That “Hunger Games” analogy seems to have stuck – many of the people I conversed with for stories over the past two weeks asked me a variation of the, “How is The Hunger Games treating you?” question.

The truth is that every interaction I’ve had with one of my fellow writers has been a combination of productive, nice, charming, and helpful.

When fellow writers finished their trials, I mostly felt sadness. Not only will I miss our conversations on The Tavern Slack channel, but I’ll also miss the energy and reporting they brought to The Tavern. This version of The Hunger Games has been a ray of sunshine to my eyes.

How did I decide what to write about?

Emotions Emotions Emotions

What did I learn in these 2 weeks of writing for The Tavern?

I hadn’t applied to a job in decades.

What is it like working with Matt?

How would I improve The Tavern?

What’s next for me?

Would I do it again?

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How did I decide what to write about?

I was surprised by the different types of content each of us writers produced for The Tavern. One of us did long-form video content, some of us were curious about reporting on new and interesting things in the WP community, some of us shined a light on long-underreported people in our community, some focused on tech, others focused on humans, etc.

As you likely noticed, I am, personally, curious about how the WP community changes and rolls with the times. For example, you saw me writing about how small businesses are taking on the big dogs, an analysis of popular themes on wp.org, and how plugin shops have integrated accessibility best-practices into their day-to-day jobs.

Emotions Emotions Emotions

While I felt very prepared to do the work that would be required, I was unprepared for the whirlwind of emotions that would flood my body during these two weeks.

Almost everyone I spoke with for my articles was exceedingly professional and helpful. In fact, some people went out of their way to help me find sources and to cajole quotes out of people.

And yet, at times my discomfort with waiting for email/Slack responses to my inquiries left me an emotional wreck (“Are they ignoring me? Did I offend them? Were my questions stupid?” etc.).

Then there were times I accidentally manufactured discomfort – like when I pushed to get a straight answer about a difficult topic out of a PR person at a big WP plugin shop.

There was the scary time when an online accessibility forum misunderstood my line of questioning and came after me with pitchforks (for the record, my articles highlight people who are making a positive difference on the accessibility front).

I think the waves of emotion I experienced are part of starting something new and challenging. I hadn’t written articles with this intensity for decades – it makes sense that I would be forced to deal with my internal emotional issues.

What did I learn in these 2 weeks of writing for The Tavern?

Over the past couple of weeks writing for The Tavern, I learned so so so much. Here are some of the many lessons I learned since Feb. 29:

I learned that people appreciate being part of a good yarn. My articles on plugin businesses and people doing great work on web accessibility seemed to be appreciated by both the commenters and the people featured in the articles.

I learned that hitting “Publish” can be scary.

I learned off-the-record conversations are oftentimes more fun than on-the-record ones.

Related, I learned that off-the-record conversations build trust that a reporter can leverage into more compelling on-the-record interviews and articles later.
For example, one of my off-the-record conversations led me to a curious string about a sensitive topic – I pulled that string, and before you know it, we agreed to put that part on-the-record and included it in an article.

I learned the hard way that you’ve got to be careful about how and where you tell people you are a journalist. That lesson cost me a lot of heartburn and sleep.

I learned that I need to help people help me. One person I interviewed early on asked, “What’s your angle? I want to give you a quote that’s relevant.” That question saved us from a lot wasted of back-and-forth time.

I learned that some people want The Tavern to be hard-hitting “gotcha” news source.
(Fwiw, I see The Tavern’s role in the community a little differently – It needs to be a trusted source of information and a hub for conversation in the WP community.)

I learned (to no surprise) that the writers at The Tavern truly do have the editorial freedom to cover topics that are critical of WP power brokers, including the people paying our paychecks.

Interacting with the other 6 writers led me to believe that any of us 7 would make great next-generation leaders of The Tavern. Seriously – I’d trust any of them with leading my beloved Tavern moving forward.

I learned that reporting on WP stuff is not an easy job.

I learned that the 2-week timeframe was both a positive driver and a limiter of output. Deadline pressure in journalism is real any way you slice it. Deadlines force you to get creative – to say “good enough”, hit the “Publish” button, and move on to the next challenge.

I learned that not as many people read The Tavern as I thought.

When I told my mom and sisters that I was picked to write for The Tavern, they were like, “Uhh huuuh. That’s nice, sweetie,” and more or less patted me on the head before returning to their respective days.

I was surprised to learn that even some of the WP pros I quoted in my articles did not check wptavern.com to read the articles. When I spoke with them a week after one article posted, they said, “Oh! Is that article live?”

I learned that, based on The Tavern’s Jetpack stats, these articles do have an extremely wide reach by my standards. For example, one article I posted has garnered over 2,000 views on the web, over 2,000 email opens, and 70 clicks from email. (I joked that I had 300 million impressions and 4,070 conversions – that’s a conversion rate of .0013%. Not great if it was a paid ad campaign, but, personally, I was thrilled with the numbers!)

I learned that constructive criticism I received on my article drafts from my fellow writers made my writing better.

I hadn’t applied to a job in decades.

One thing I found personally fascinating was the application process – because I have no idea how to apply for a job.

The last job I applied for was a student life position at the University of Minnesota in 2004. I quit that job in 2006 to become a WordPress consultant, which has been my primary job since.

Writing for The Tavern is a dream job for me. In my application, I wanted to communicate my vision for the job, my unique life experiences that might make me a great fit, my view that the news is a critical component of our democracy, as well as my quirky personality (didn’t want to surprise anyone there).

My application was a long email highlighting my experiences reporting the news, blogging, and contributing to the WP community. It also mentioned my respect for The Tavern’s history (I’ve been reading The Tavern nearly every day for 10 years or so).

When I didn’t hear back after a short amount of time, I got antsy and sent this follow-up:

When I didn’t hear back on my original application after a week, I sent this follow-up email.

What is it like working with Matt?

One of the more popular questions people asked me over the past two weeks was, “What is it like working with Matt Mullenweg?”

Matt was true to his tongue-in-cheek word from his Nov. 2023 post: “You can ask previous writers how much I was in their hair.” I had very few interactions with Matt or the Automattic/Audrey team.

I felt prepared to do the work of The Tavern, and I saw the lack of interactions with Matt as a sign that he trusted me to do that work.

I felt like Matt was available via Slack if I needed him, however the only time I needed him was when I needed access to the X.com account.

Also, I had read The Year Without Pants, so I was expecting this trusting, hands-off approach to leadership.

So, with all that in mind, it was great working with Matt!

How would I improve The Tavern?

I have a great love in my heart for The Tavern. Regardless of who takes over the reins, I hope they continue to pursue a deeper connection to the WP community.

The Tavern is a hub of our community – a place where people go to learn and to be heard. The format and history of The Tavern communicate an openness that has proven tough to replicate elsewhere on the web.

At the end of the day, wptavern.com is the humans who write, run, and interact on the website. I hope whoever takes over continues to push those traditions.

I see an opportunity to have the Tavern community provide more input into what gets reported on.

I can see the next leader reimagining the WP Tavern Forums, doing more outreach on other platforms, and looking for other ways to increase engagement on-site.

What’s next for me?

I don’t know what’s next. I feel like I could add some very positive and subjective direction to The Tavern based on my unique experiences in the WP community.

To be honest, I would love to be involved with The Tavern in any capacity that it needs me.

Would I do it again?

It’s been a thrilling couple of weeks, and I’ve gone through a rainbow of emotions and learnings.

I would absolutely 100% do it again. And who knows – maybe you’ll see this smiling face at The Tavern again someday!

Toby Cryns is a freelance CTO, WordPress consultant, and teacher at The Mighty Mo! Design Co. in Minneapolis, MN, USA.

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