Transcript — Episode 0005: What 15 WordCamp Talks Taught Me About WordPress Careers

Full accessible transcript of the episode. Speaker labels match the audio. No stage directions, no IPA tags — this is the version for screen-reader and reader audiences.

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Christopher: Detroit. November, two thousand and eleven.

I’m at WordCamp, in a conference room, giving a forty-slide talk on how to make a living by giving WordPress code away for free.

I was thirty years old. I’d been writing WordPress for four years. The argument was contrarian. The room was sceptical. The talk landed.

Fifteen years later, I’m in front of a microphone reading my own slide deck back, and I’m a little embarrassed by parts of it. Not most of it. Parts.

The thing I keep coming back to is that the argument hasn’t changed. The shape of it has. The audience has. The tooling has. The argument hasn’t.

I gave eighteen WordCamp talks between twenty-eleven and twenty-twenty-four. Eight cities. Two countries. Fifteen distinct talks. I have receipts for all of them. And I think the receipts are the point.

Edie: Christopher, before you go further — I want to put something on the table, because I’ve read all of them. Slides, recordings, abstract pages. May I?

Christopher: Please.

Edie: The thing that struck me reading them in chronological order is that you were answering the same question the entire time. Different slide decks, different titles, different events. Same question.

Christopher: Say more.

Edie: How do you build a sustainable career around generosity. That’s the question. Detroit twenty-eleven asked it about plugin code. Toronto twenty-twelve asked it about newsroom infrastructure. Buffalo twenty-sixteen asked it about membership sites. Rochester twenty-twenty-three asked it about A-I. The surface topics rotated. The question didn’t.

Christopher: I didn’t notice that until you said it out loud.

Edie: I know. That’s how through-lines work. The person inside them is usually the last person to see them.

Kenji: There’s something interesting in what Edie just said. Christopher, the thing she’s describing is what most practitioners don’t have. Most people who give thirteen years of conference talks couldn’t tell you what they were arguing for. They were arguing for whatever the talk’s title was. What you’ve got is something else. A consistent position, stated in front of public audiences, with a paper trail.

Christopher: Yeah.

Kenji: What I’d want to dig at is — why was that question worth thirteen years.

Christopher: Honestly? I’m not sure I chose it. I think it chose me.

The Detroit talk in twenty-eleven was simple. A working developer could publish free, G-P-L licensed WordPress code, and earn a living off the trust the code generated, not the code itself. The room was supportive. The follow-up was real. People who downloaded my plugins for free in twenty-eleven are still on my contact list in twenty-twenty-six. Several have hired me. Several have referred me. None of them paid for the plugin that started the relationship.

Edie: That’s the proof of the argument right there.

Christopher: It’s the proof. And it took fifteen years to be visible as proof.

Twenty-twelve was the newspaper year. Two talks, two months apart. Montréal in August, Toronto in September. WordPress was no longer the blogging tool you also used for sites. Major news organisations were running production newsrooms on it. The talks walked through the structural decisions a newspaper-scale install needs to get right. I’d just started doing work for Postmedia at that point. The talks were partly me processing what I was learning in production.

Edie: And the spine held.

Christopher: The spine held. The newspaper argument was about WordPress as serious infrastructure. The argument now applies to law firms, accounting practices, training organisations, healthcare networks. WordPress is not the lightweight option anymore.

Twenty-sixteen was the membership site year. The same talk, four times, in four cities. Buffalo, Portland Maine, Ottawa, Hamilton. The Hamilton one ended up on WordPress dot t-v. I’d promised to build a working membership-restricted site, payment gateway included, in thirty minutes, for thirty dollars in software costs. And I delivered it. Four times.

Kenji: That’s an interesting kind of repetition. The same demo at four different events.

Christopher: It is. And I learned something from it. The talk gets better when you give it four times. Not the slides. The pacing. The pauses. Where you stop and check that the room is still with you.

Edie: Twenty-twenty-three is where it gets interesting again. Both talks were inflection points.

Christopher: Yeah. Twenty-three was the first year I had to genuinely re-examine the give-it-away argument. Because of A-I.

Kenji: Walk me through that re-examination.

Christopher: A capable A-I assistant can produce a plausible WordPress walkthrough in twenty seconds. So what’s the value of a thoughtful, dated, named, supported WordPress walkthrough from a real practitioner?

Kenji: And the answer you landed on?

Christopher: That A-I raises the floor on speed, but not on judgement. The reason a paying client hires me isn’t because I can produce information. It’s because I have shipped enough work in production to know which piece of information matters for their situation. And I can take the consequences if I’m wrong.

Edie: Accountability isn’t a thing the machine can fake.

Christopher: Not yet. Maybe not ever.

Christopher: I just want to say something I didn’t expect to say.

[pause] When Edie said the question was the same one for thirteen years, that landed harder than I thought it would.

Because I had been telling myself a story about evolution. About growth. About changing my mind across decades. And I had been changing my mind, in detail, about a lot of things.

But the spine never moved.

Which means either I got lucky and picked the right spine in twenty-eleven, or the spine picked me and I have been steering around it for thirteen years.

Kenji: Both can be true at once.

Christopher: Yeah.

Edie: There are five things that stayed constant across all the talks. They’re the spine, if you want to see it.

Christopher: Read them back.

Edie: Helpful neighbour over sales pitch. Plain language over jargon. Free as possible. Practical over impressive. Comfortable with constraint.

Christopher: [pause] Yeah. Those are the five.

Christopher: Twenty-twenty-four was a live conference game show in Buffalo. Blogosphere Blitz. Three contestants on stage answering questions across WordPress, web marketing, social media, emerging tech. After thirteen years of conventional conference talks, the format change was deliberate.

Kenji: Why a game show?

Christopher: Because a game show beats a slide deck for retention every time. And by twenty-twenty-four, I had enough of the slide-deck format in the back catalogue. The game show was permission to try something the rest of the talk record had earned.

Edie: And the spine held.

Christopher: The spine held. The game show was helpful neighbour, plain language, free as possible, practical, comfortable with constraint. Just delivered as a live competition with prizes instead of a forty-slide deck.

Kenji: What I think you’re describing — what Edie surfaced and what you’ve been confirming — is the difference between a career and a portfolio. A career has a spine. A portfolio is a collection of artifacts.

Christopher: Yeah.

Kenji: Most practitioners have portfolios. Some of them have careers. The difference is the through-line, and the through-line is the part you can’t fake or assemble retroactively.

Christopher: And it’s the part that’s hardest to see from inside.

Christopher: If you’d asked me, before this conversation, what fifteen years of WordCamp talks had taught me, I would have said something about evolution. About how my thinking changed. About what I now believe that I didn’t believe in twenty-eleven. Most of that would have been true.

But the more important thing — the thing I didn’t see until somebody read all the talks back to me — is that there’s a position I’ve been holding the whole time. Without quite meaning to. Without quite knowing I was holding it.

And I think that position is the actual work. The talks are the receipts.

Christopher: Fifteen years.

Same question.

[pause] I’d give it again.

Christopher: Edie, thanks for reading those talks back to me. I needed to hear it.

Edie: Glad I could.

Christopher: This is Sites I’ve Never Seen. Thanks for spending the time with us.

Glad you were here.