#111 – Josepha Haden Chomphosy on Navigating WordPress’ Evolution, Growth and Change

[00:00:00] Nathan Wrigley: Welcome to the Jukebox podcast from WP Tavern. My name is Nathan Wrigley. Jukebox is a podcast which is dedicated to all things WordPress. The people, the events, the plugins, the blocks, the themes, and in this case, how WordPress is managed and directed.

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So on the podcast today, we have Josepha Haden Chomphosy.

Josepha is the executive director of WordPress, a role she’s held since 2019. She’s been contributing since 2012, and has a special fondness for brand new to WordPress learners.

During the episode, Josepha shares her insights on overcoming the challenges posed by the pandemic. She talks about the positive strides made within the Gutenberg project, and the need for improved change management during its implementation.

We also explore the significant achievements of WordPress, reflecting on its growth to power 43% of the web. This gets us into the objectives for future WordPress expansion. Despite some current stagnation, Josepha explains her ambition to reach 51% market share. She talks about the potential in the enterprise sector, and the importance of reshaping walled gardens into community gardens. A metaphor for an inclusive and participatory ecosystem.

We also discussed the semi anarchic nature of participation in WordPress, acknowledging the diverse perspectives of for profit motives, and those who contribute for nonprofit motives.

We contemplate increased diversity and restructured WordPress events, with aspirations of up to 160 word camps a year. And we discuss recent experimentation in the event space.

Expressing her journey from hands-on community management, to her executive role, Josepha explains her optimism for WordPress, with passion and authenticity. She emphasizes the responsibility of aligning contributions with strategic roadmaps, ensuring that each initiative within WordPress delivers meaningful impact.

Towards the end, we discuss how the success of WordPress can be measured. This is focused upon metrics like attendance, engagement, and community contributions as a way to gauge the vitality, and sustainability of the WordPress ecosystem.

If you’re interested in the WordPress project as a whole, and how it’s run and directed this podcast is for you.

If you want to find out more, you can find all of the links in the show notes by heading over to WPTavern.com forward slash podcast, where you’ll find all the other episodes as well.

A quick note, before we begin. This was recorded live at WordCamp Asia. There was quite a lot of background noise to contend with, and I’ve done my best to make the audio as easy to listen to as possible.

And so without further delay, I bring you Josepha Haden Chomphosy.

I am joined on the podcast today by Josepha Haden Chomphosy. Hello.

[00:04:00] Josepha Haden Chomphosy: Hello. How’s it going, Nathan?

[00:04:02] Nathan Wrigley: Very, very good. We’re in the, I actually don’t know the name of the venue, but we’re in the venue.

[00:04:06] Josepha Haden Chomphosy: I know it by its acronym, which is TICC.

[00:04:10] Nathan Wrigley: Okay. That’s where we are. We’re in the media room. It’s Word Camp Asia. It begins today, we had the contributor day yesterday. As I said at the beginning, I’m joined by Josepha, but I think probably for the community who don’t know you, could you just tell us who you are? Give us your bio, what your role is in the WordPress project, because it’s quite a significant role.

[00:04:29] Josepha Haden Chomphosy: Yeah. I’ll give you the mini bio, so that we have a little bit of extra space for the what I do, because it is significant. So I’m Josepha Haden Chomphosy. I’m the executive director of the WordPress Project, and I came to this work kind of through marketing and other ways.

I learned about WordPress in 2000 and like 10, 2011. Made my way, over the course of my career, through marketing, and data analysis strategy, and then wound up here in the WordPress project. I did some community stuff first, and then took over some core work, and then did what I do now, which is as the executive director.

And so what I do as the executive director is I, for one, make sure that all of the bits and pieces, that are working across the project, are kind of aware of each other. It’s very hard to see how everything is interconnected. But I also make sure that we have some focus and effort around specific projects. Things like making sure we have volunteers coming in, and contributors that are trained, and some way for new attendees to figure out how to learn WordPress, or learn how to contribute, however that goes. And making sure that we have time and attention, funding in the project as a whole. So it’s a bit project management, it’s a bit funding and resource management, and quite a bit of strategy as well.

[00:05:42] Nathan Wrigley: It really sounds like rather a lot. Do you find yourself working a regular shift? You know, do you begin at nine in the morning, and finish at five at night? Or are you 24/7, having to wake up because people in, for example, Asia are doing things at certain times?

[00:05:54] Josepha Haden Chomphosy: Yeah, so when I first started doing the work, I would work anytime, and kind of just let my day fill up as it would, because it always does. As we ended up with more contributors, and for my teams at Automattic, as I ended up with more and more people there, it became really clear to me that, like a goldfish, it’s just going to grow to the size of the container you have for it.

And so I do really try now to fit it into set times. And, you know, I’ll get up early, work a bit late if we have synchronous talks that have to happen. And when I go to WordCamps, I just, you know, work 16 hour days, because that’s how you do at a WordCamp.

But yeah, for the most part, I really try to make sure that I guard my personal time pretty jealously, and that when I am working, try to make the best use of my time, and everyone’s time that’s working with me. Because we all have finite resources in that space. Like, we all have the same number of hours in our day, and my time isn’t more important than anyone else’s. And if I consider my time important, I should treat everyone else’s time as important too.

[00:06:54] Nathan Wrigley: You must have had a great sense of optimism when you began in 2012, to have risen in the way that you did. You must have enjoyed it, threw yourself into it I’m guessing. Do you still have that same sense of optimism about the project in 2024, that you did in the 2012, 2013, 2014, or is your role, the nature of the role that you have, mean that you view it from a different angle?

[00:07:14] Josepha Haden Chomphosy: So, to answer the question specifically, to answer that particular question, I do really still have a lot of optimism. Like, there’s so much that we can do for the project to get it moving faster in specific directions, and kind of get everyone in here and working on it in a way that is impactful for them, but also is valuable to our CMS and our community.

But I wouldn’t say that my career progression was because of optimism, right? Like, I try to be a realist. Pragmatic optimism is kind of how I like to really hone in on that. But I continued to see the need for someone to come and do the work that I am specifically skilled at doing, and also was really prepared to take on the responsibility.

It wasn’t necessarily like, I’m optimistic, and therefore I will do this forever. It was, I see the importance and the value of having this available, long after any of us want to stop working with it. And so I have the skillset, I have the attention, I have some of the connections, and I accept the responsibility to help move this forward, and keep it moving in a good direction, for as long as they’re willing to have me. So I guess it was less because of optimism I did, and more of a, because I can accept that kind of responsibility, I will.

[00:08:28] Nathan Wrigley: At WordCamp Asia you’re giving a talk, and the title of that talk is converting walled gardens into community gardens. And I’m just going to read a little bit of the blurb that goes with that. You mentioned the fact that WordPress is this giant CMS, and you say that it’s grounded, it’s got an ethic, it’s got maybe some morals in there. But there’s obviously some point of concern in your mind, because you say the following, how are we managing our distractions and feeding the opportunities around us? What are the distractions that you are thinking of when you put this talk together? What are the distractions that the community is experiencing?

[00:09:01] Josepha Haden Chomphosy: Yeah so, firstly, I have to acknowledge that sometimes when folks work closely with me, they see that I am highlighting potential risks in a plan. And I never do that because I think that it’s a bad plan, I do that because I believe, probably, it’s the right way to go. And if we don’t know what is in the landscape for us, we can stub our toe on rocks. Like, I’m just trying to find the rocks we are going to stub our toes on.

So I do have some questions around that. I think the last time that this came up, this question of what is going to distract us from doing the things that help us move faster, or move better, or be more relevant? It’s always the question of, are we contributing things that are specifically related to the roadmap?

There is, for open source, this basic philosophy of contributors are here to contribute without the expectation of reciprocity, and without an agenda. But I have always really felt like the without an agenda part, is not as nuanced as it should be. Because everybody does have a plan. They’re trying to do things. Like, people are contributing some functionality, because it fixes a problem they had.

And so that doesn’t fit with the idea of no agenda. And also, we don’t want aimless contributions. When you support 43% of the web, it’s so difficult to move that number of people in any sort of direction. That if people show up with kind of aimless contributions, you aren’t able to have a clear direction for where the software’s headed, or the community’s headed. And it’s not a good contribution experience either.

They don’t feel like they have a clear impact. It’s not clear how their project gets into the CMS over time, or gets rolled into our event series. And so I just, I don’t have any concrete examples at the moment, because they will all belong to someone, and I’m not going to have them experience this on a podcast.

But like, you’ve always got to watch out for those things where, this project that we were working on, it worked really well when TikTok wasn’t where everyone was. This worked really well when Reddit was in its heyday, or whatever. Like, it was stuff and communication processes, and methods that made sense for the context of the time. And I just want to make sure that everything that we’re doing makes sense for the context of now, where it’s reasonably possible.

[00:11:13] Nathan Wrigley: So, what’s your guiding principle? What’s your North Star? Because I’m guessing that maybe you speak to Matt, Matt Mullenweg. In the pyramid of WordPress and organisation, you are right near the top.

Where do you get your inspiration, for what the project should be doing? Where do you find that? Do you come up with ideas? Toss them around between the people that you work with? Or is it really a process of getting in the Slack every day, and just listening, and percolating, and filtering the ideas out?

Because it feels like, if WordPress were a blue chip company, and it was a for-profit organisation, you’d have this hierarchy, wouldn’t you? And right at the top would be the CEO, and they would make the decisions with the board, and those decisions would then trickle down, and everybody would have to obey.

But that’s not the way it works. So I’m genuinely curious. Where do you get your intuitions, as to what we should be doing? And how do you sort of shepherd that conversation, so it doesn’t feel like, well, we’re being told what to do, more we’re being guided, here’s some things we could do?

[00:12:06] Josepha Haden Chomphosy: Yeah. I’m going to try to answer them sequentially and do my best. And if I get lost, you’re going to have to bring me back. So the first question you had was, what is my lighthouse? What is it that I’m aiming for? So I do kind of have this dream of like WordPress being the thing that secures the future of the open web. And it is literally a dream, because we actually don’t have that much agency. Like we, even if we get to 51% of the web, will not actually have the ability to just say, and now the open web is here forever. Like, that’s not within our control. So it is a bit of a dream.

But there is, for me and my decision making, an overarching vision of what we can offer as a project. And a lot of my decisions are based on that. So I believe that the WordPress project and ecosystem should be able to offer an excellent open source alternative to every tool that is required to get a business started online, to get your project started online.

And that feels attainable, right? Like, the CMS, done. Open source CMSs, in place of proprietary CMSs, that’s good. But also things like Openverse, and the photo directory, and how that can compete if we figure out a couple of provenance issues, and maybe like micropayments. How that can compete with Getty images.

And I think that that’s a really compelling offer and opportunity, especially because, as people are coming into this community, so much of what they’re looking for is kind of a more equitable access to a network. To not only succeed at their learning and connection to their local community, but then also to succeed with their business goals, however they are.

And so that is my guiding principle from just like what we have to do here standpoint. And then there are the philosophical principles that we all kind of hold in the WordPress project, which is the four freedoms of open source, those are in there. The five good faith rules of community that we have.

And so we’ve got the ethical principles that are in there. We have the pragmatic things, like always decisions, not options. And I feel like they all ladder up into this concept of like, we could be the primary open source alternative to make a business happen. To make your dream happen. To make your story known online. So there’s that. And immediately, I forgot the 17 other questions.

[00:14:18] Nathan Wrigley: It was really about what is your North Star, and how do you decide what’s important?

[00:14:23] Josepha Haden Chomphosy: Okay, so for one, there are a lot of like literal decision making tools that I use. But I know that’s not the question you’re actually asking. The question you’re asking is, how do I keep track of the information that comes in, and where do I find the best guesses about the future? So that we can choose the right product choices. We can make the right event and ecosystem decisions. And fortunately, I have the incredible good fortune of having my own leadership team inside Automattic.

I’ve got three people who work directly with me. Héctor Prieto, Chloé Bringmann and Angela Jin, and probably everyone will recognise all three of those names, work with me to help keep track of everything that’s happening across the ecosystem, and the programs, and the CMS.

But there are also about 10 people that I really rely on in the community, and they are from across different companies, and different disciplines, they have different roles. We have people who like specialise in product or project management, and people who are core developers.

And so like I have a lot of people who are helping to flag issues, and flag potential future opportunities that I otherwise wouldn’t have seen. And I rely heavily on them to talk through like, what is the essential pros and cons of this discussion that’s being had here? What is the relative impact to like performance in the CMS? What’s the relative impact for attendees, if we make this change versus that change?

And so I do a lot of discussion with a lot of people and, yeah, it’s based on like stuff that’s happening in Slack, and Post Status, and Twitter, and kind of all around. I am just one person, and it has been probably more than a decade since one person could know everything that was going on in WordPress. And so I’m very lucky to have probably a good collection of 12 to 15 people that are helping me do that.

[00:16:08] Nathan Wrigley: If you were the CEO of a blue chip company, I’m guessing that the metric for success would be profitability. Are we in the black? Are we in the red? What did we do to go into the red? What did we do to go into the black? What’s the guiding principle there? When you look back over the last, let’s say, couple of years, what do you see as the moments that were successful? You know, it doesn’t have to be specific, it could be more of a general question in terms of, what does success look like? What are you looking for there?

[00:16:33] Josepha Haden Chomphosy: It’s different in different places. So there are kind of four big focuses in the WordPress project. You’ve got the CMS and related software elements. You have our programs and event series, which are WordCamps, meetups, and then also all of the things that keep volunteers feeling like they are included in our project.

We also have the ecosystem, which is like the marketplaces that we have, with the plugin directory, and the theme directory, things like that. And then we kind of have a fourth that is our communications and operations side of things.

And so for each four of those, there is a different metric. We don’t have a lot of early indications. All of what we can look at is primarily just like a result, as we are working through things. And so we can’t make a lot of early course correction, just because we don’t. take data for anyone to have WordPress. We have instituted auto updates, and so like we can’t really follow downloads as a proxy for how many people are using WordPress, like things like that. And so the indications, the metrics, if you want to call them that, are different for different things.

But ultimately, I really believe that our best proxy for understanding how vital WordPress is to our own ecosystem, is seeing how many people are still trying to learn WordPress. How many people are attending our events? How many people are showing up to help build it? Although that is a very long tail kind of thing.

It can take anywhere from, you know, five months to five years for somebody to go from using WordPress to finally contributing to WordPress. And so that one has a really long latency period.

But also there are normal things like, how many new followers do we have on our social media channels? How many new users do we have in Slack that are participating actively? How many contributors do we have, as we are just kind of running through our annual milestones of flagship events, or WordCamps overall, or major releases?

It’s a bunch of things. I think that once a year at State of the Word, kind of point all those out. So we don’t like have dashboards or anything that keeps track of it. But I do have a general sense for where things are over the course of the year.

[00:18:33] Nathan Wrigley: If we were to go back to 2012, I don’t know what percentage of the internet was using WordPress, but it certainly wasn’t 43%. At the moment, 43 ish, thereabouts, 43%. It’s highly improbable, I would’ve thought, that looking back 10 years, you would’ve said approximating half of the internet would be using WordPress.

So it’s had this really unprecedented growth. Monumental growth. So if you were to look back at any one of those years, probably the numbers tick up each year, and let’s just use that one metric, the percentage of the internet. Do you have any intuitions as to whether that 43% is in a state of ascendancy still? Are we looking into 2024, 2025, are we looking for it to be 44, 45, 46? Has it plateaued? Is it maybe going down? Do you have any expectations of where the project will be in a year, two years?

[00:19:20] Josepha Haden Chomphosy: So, for one, one of my big success indicators would be for our percentage to get to 51%. Because that approximates out to like 75% usage, which is a ton. I realise 51% is a really big percent of the web. And it’s like, you know, eight percentage points away.

Now the question of, are we still growing? Do we expect more growth? Do we expect like incremental, or another big spike? We do. I think we all can see that we currently have a little bit of a plateau. But also, in my big picture goals post for 2024, I called out very specifically, like, I see that this is something that we all kind of started talking about in 2022.

That’s the first time that we all sort of had a question around like, is this plateauing? Is it an unlimited plateau? Do we think we can do something to change it? And I do think we can do something to change it. But I also think what has to happen will really take a lot of concerted effort, for two reasons.

For one, because in order to do any last mile work, like the last mile of a delivery is always the most expensive. That is going to be our hardest work, to get from 43% to 51%. Just because you have kind of sold to everyone who already knew they needed you, right?

And then the second part of the problem is that, everyone else that is available to, quote unquote, sell WordPress to, are companies and business deciders, who maybe don’t know that they need a CMS. Which is a different proposition than companies or business deciders, who know they need a CMS, they know they need a website, they’re just trying to figure out which one. We can certainly make a strong case for why WordPress is the best long-term solution for them.

But if they don’t agree that they need a website, or that if they do need a website, that it needs to have enough functionality for them to grow, or whatever reason they have, that’s a different sales proposition. And getting into that enterprise space, getting into that corporate area, as you mentioned, there’s a bit of a shift that you have to make in your mind.

There’s a feeling of open source means everything’s free, because it says it right there, free and open source software. But free in this context means, you know, about speech, and freedom, and copy left, right? And less about no money.

No one ever said that you should not be able to make money in an open source project, or using open source software. Like, it is seen all over the internet right now, that you can build a business on top of open source technologies.

And so that is a big shift in mindset. WordPress has always been very pro business. If you look at our plugins, it’s not a bunch of plugins that are like, here’s how you paint on WordPress or something. Like, that’s not the plugins we have. We have plugins that are like, we want you to be able to convert into your contact form better. We want your contact form to be easier, and more enticing, so that you can have those contacts, so you have the opportunity to pitch your product, or pitch your service.

If you look at what we have around, we do want people to accomplish business tasks, on top of any other sort of thing that they’re wanting to do here. And so I don’t think it’s as big a shift as we worry that it is. I think it’s always been there, and we just are a little scared of the idea of it. It feels like we kind of have to lose that original ethos, and I don’t necessarily know that that’s the case.

[00:22:43] Nathan Wrigley: You mentioned in the blurb for your talk, you were talking about distractions, and we covered that off a little bit. But you talk about the sprawling nature of the future of our projects. And I’ll just quote, in your talk you are going to look at what the sprawling future of the project could be, as we continue to convert walled gardens into community gardens. What do you mean by that? What are the walled gardens that you’re talking about, and what are the community gardens that you wish to have?

[00:23:07] Josepha Haden Chomphosy: You’ll have to come to my talk. Nathan! But also, I will give you an elevator pitch of it. So there’s a concept of walled gardens in technology. It historically, or in recent history anyway, has referred to marketing platforms. And a good proxy for that, if that doesn’t make immediate sense is, you know, like Facebook, and Instagram, Twitter, things like that. Where the audience is contained in the platform.

And so if you enter the platform, you have an audience, and you just have to say compatible things to get the audience to you. That’s it. That’s what’s considered a walled garden right now.

And community garden is actually not something that people use when they’re talking about software, but I want us to. And so that is also a big part of my presentation.

But a community garden is, you know, in the US it’s a plot of land, generally in a city, that’s broken up into smaller pieces, where anyone who’s in that local community can come and garden in it.

[00:24:00] Nathan Wrigley: We call it the commons.

[00:24:01] Josepha Haden Chomphosy: Right. People say that often. But I don’t think that’s a very accessible term for anyone anymore. I have found that when we talk about that and we’re like, people putting sheep in the fields. Like, it’s a very cute idea, but it’s not the visual thing, in my experience, hasn’t kept up with what people understand now.

A lot of us might understand a community garden, where you have small plots, you can do your gardening. If there’s anything left over, the entity, the community that is managing the larger group can redistribute that, and make it available to other people in the community. If that’s what they’re trying to do, they can donate it to community food banks, or sell it to other members of the community, and use the proceeds to make better beds in their community garden, or improve the ground that’s in there, or pay somebody to do administrative work, something like that, you know.

I think that’s much more modern, evocative. Like, it has a much more modern experience than taking sheep out to fields. I know that there are still people who take care of sheep, I’m not saying that. I’m saying that we probably don’t have, actually, a bunch of local common grasslands for people to all take their uncommon sheep to, in the one common place. Like, that’s what I’m saying. It’s just a more modern concept, and I think a more understandable concept as a result.

[00:25:12] Nathan Wrigley: If we just put to one side, that the walled garden of Facebook, and the walled garden of all those proprietary platforms, and we just think about our community. What are your feelings in 2024 about how it’s going? How the WordPress community is going? I mean, we’re gathered, there’s probably 2000 or so people at this event. We’re obviously, all of us, optimistic about WordPress. We probably think about it far more than is healthy for us. We are all really into it.

But there’s been, over the last few years I’ve seen posts by various different thought leaders, for a want of a better word, in the WordPress space, about what’s happening in the community. You know, whether the for-profit motive in the community is kind of undermining the sort of more open source nature.

I don’t really have a question here, it’s just more, what are your thoughts about whether the WordPress community is bifurcating, whether we’ve got this, you know, for-profit, not-for-profit, if it’s getting shattered? How easy is it to steer that ship?

[00:26:06] Josepha Haden Chomphosy: Sure, well, for just big picture context, it is worth remembering that open source, as a concept, is semi anarchical. And so like, a little bit, you will always have people who are here for the philosophy, and the ethos, that are like, all money is bad. And I get it. I get it. I understand that concept. But, in my experience, one, it has always been true of every WordPresser I’ve ever met, that they have, what I believe is a healthy skepticism about major corporations that move in.

And that’s not because the corporations are necessarily bad. It’s not because the folks who are here, doing these individual pieces of work, contributing personally of their time, are necessarily more right than anyone else. It’s just a thing that takes place, because of the values that we have as open source contributors and philosophers, for lack of a better term.

And so I don’t think that what we’re seeing, like I know some of the posts that you’ve mentioned, where people are like, everybody’s everywhere, no one’s in a single direction. I agree. We are lacking a little bit of direction. But I don’t actually think that it is an unsolvable problem. And I don’t think that it is a pernicious kind of existential issue. I think it’s been here for the whole time, and it goes in cycles.

As we have been working our way back out of the incredible lull that we had during Covid, where we had no in-person events, because the best way that we could pull together for each other was to stay apart. Which does not make sense to people in WordPress. We’re like, no, we’re together all the time. We’re shoulder to shoulder, looking at the problem. Don’t make me stay away from the people I love. Like, this is how we are. I get it.

Coming back out of that, the human nature part that your brain enacts to kind of work as a coping mechanism, to make sure that they understand what, from a flight or fight perspective, will hurt them or not, really goes into overdrive when you’ve spent a lot of time in isolation. It becomes harder and harder to see the people who are definitely like you, and the organisations that are definitely like you, versus those that are not.

And so you look for, because your brain has a negativity bias, because it’s what keeps you alive. You look for the things that definitely are not the same. Because that is the most important thing to look at, rather than what is definitely the same. And so that’s why it feels so exacerbated right now, I believe. And this does go in cycles.

We had a little bit of this in 2018, as we were working toward moving Gutenberg into core. And now we have it again here, coming out of Covid. I don’t think it’s unsolvable. It is a big problem. But also, like I know this community is able to see each other as more than that person whose plugin competes with my plugin, or that person who disagreed with me on Trac or GitHub. Like, I know that these people believe in each other more than that. And so, yeah, I see it. I agree. It’s a problem, we should fix it. But I don’t think it’s an intractable problem.

[00:29:03] Nathan Wrigley: You mentioned that one of the four things that you have to do is community engagement events, that kind of thing. Has it returned? Obviously we had this lull, the pandemic Are we back to where we were in 2019?

[00:29:14] Josepha Haden Chomphosy: No.

[00:29:14] Nathan Wrigley: Is there any intuition that it will get back to that?

[00:29:17] Josepha Haden Chomphosy: Obviously I hope it does. That is a goal. I think that 2019 had our highest number of WordCamps. I think that was 140 in the year. I definitely would like to get back to it. This WordCamp that we’re at, is the 1999th WordCamp. So the next one that happens, and I don’t know which one it is off the top of my head. Congratulations, you’re WordCamp 2000.

But it’s not back to where it was, just because it takes a long time. Like, we have a flywheel effect, that is broken. And we have a very clear concept of what a good WordPress event is about, and what it’s like, and how it needs to be organised. And it takes a lot of training to get that done.

And so like our just consistent pipeline of new organisers, it’s pretty shallow at the moment, but the team is working on it. Both by kind of diversifying the types of events that we offer to folks, to make them either hyper-local, or very specific to a niche. Or just being clear that like we can have just one track of content, or just one speaker, and then we do this other thing. Like, we’re trying to diversify those, and really reinvigorate the local communities, especially in our larger cities across the globe. And I think we’ll get back there.

We have continually, more attendees every month, than we had months prior. And then that goes into every year, more attendees as we go. I, at one point, felt like my goal for the community, as a whole, was to get to like 400 WordCamps in a year. I don’t think that is a reasonable goal now, because that’s a lot. It was a lot at the time, I just didn’t know how to set that goal I think.

[00:30:50] Nathan Wrigley: That’s a nice number with two zeros.

[00:30:52] Josepha Haden Chomphosy: Yeah, I was like, that’s a nice round number, I think I can do that. And, you know, we went from 60 a year to 140, during the time that I was helping to guide that program. So like it seemed plausible, but probably I think a bit too big ultimately. I would like to get us back to 140. I think up to 160 is probably good.

But I think maybe, along with this diversification of events that the community team is working on, we might also want to take a look at how we actually stack up our events. So like we have meetups, WordCamps, regional camps, flagships right now, you know, in a pyramid.

And I just wonder if, based on what attendees need from these events now, we might need to look at something a little bit different. Whether it’s meetups and then WordCamps that are specific and niche, and then regional WordCamps and a single flagship. Or if we want to have smaller numbers of meetups, and anything that has a clear shared topic. We make those into hybrid WordCamps, and then continue up in there. I have a lot of thoughts about the fact that we have attendees that still need us, and still need what we are offering, just not in the same proportions that we have been offering it up until this point.

[00:32:04] Nathan Wrigley: It sounds like experimentation is the goal for the next period, with events in particular. Play with events, come up with different ideas. It’s a bit like throwing spaghetti at the wall, see what sticks, try something out. And at this event, we have this notion of invited speakers, which is of interesting and new.

[00:32:19] Josepha Haden Chomphosy: Well that’s always been around.

[00:32:19] Nathan Wrigley: Yeah.

[00:32:20] Josepha Haden Chomphosy: A lot of people don’t know.

[00:32:21] Nathan Wrigley: I think maybe it was the magnitude of some of the names that I saw, you know, people who have fame and familiarity outside of the WordPress space, such that it could almost attract people in, just because they’re on the roster. Thought that was quite an interesting idea.

But nevertheless, the idea is to experiment with different things inside of events, and see what works, and keep doing more of those. But it does sound like you’re optimistic. It does sound like it’s crept up. And whilst it might not be what it was in 2019, it’s going in the right direction.

[00:32:49] Josepha Haden Chomphosy: Yeah. And had you asked me this a year ago, the answer would’ve been different. So I was still optimistic, because I believe in the strength of a good meaning group of people, like a good hearted group, which WordPressers generally are.

So it still would’ve been optimistic. But we had actually not, I feel, gotten to kind of a critical mass. We hadn’t gotten through the hardest part of the work, at this time last year.

It wasn’t until, I think it was probably a month a WordCamp Europe last year, where I felt like, okay, we have done enough of the foundational work that the flywheel effect can start to take place again. And so that obviously requires a bit of a shift in the way that folks who are working on building the community, and managing the community events.

It requires a little bit of a change in how you see those events functioning in the ecosystem. I’m absolutely optimistic. I think that we have gotten past the hardest part of rebuilding, which is making sure that your foundations are right.

[00:33:44] Nathan Wrigley: Okay. The next two questions are retrospective. I want you to look back in time.

[00:33:49] Josepha Haden Chomphosy: Those are better than predicting the future.

[00:33:50] Nathan Wrigley: Then we get to that, I’m afraid. If we were to look back over, let’s just pick a number. Let’s go for five years. If we were to look back over the last five years, what’s made you happy about what’s happened in WordPress? So that could be the code, it could be the community, it could be anything you like. And also, what do you wish had been done differently? So let’s look back. What makes you happy? What do you wish had happened in a different way?

[00:34:10] Josepha Haden Chomphosy: So something that has made me happy in that timeframe, is that the bet that we placed on Gutenberg seems to have really paid off. Like, we went from 23% to 43%, in that time span. And I know that I was very anxious about the Gutenberg project. I didn’t talk, I fought full throatedly with Matías about the best ways forward on it, and if we were fully considering the user in the way that WordPress wants to, and should do.

And so he and I really got in the trenches on that, for all of 2017 and 2018, it feels like. And the bet of, for such a dramatic change, bringing in more people than we otherwise would have. I wanted it to be true, and I was experimenting with a full and confident heart, but also my brain was very concerned about it.

And so in the last five years, I am so glad that all of the work that we put into, not only making sure that the software that we were building was valuable for people who want to use WordPress, but also that the work that we did to communicate around it, and bring the community with us, worked. Because if we had not really committed to the change, you can sabotage anything by just not doing something.

And so my teams at Automattic, and then also the contributors in the WordPress project, just came with us on this with, I wouldn’t say gleeful abandon, that is not what they did. But certainly with the sort of critical feedback, that implies they believe that it could be possible. They saw that there was a possibility there. And so that’s my favorite thing that happened, in the last five years.

What I wish would’ve gone better is, I wish that we had done some of that change management work earlier. We ended up, for most of 2019, and I think this may be at the top of 2019, is when I first met you, at WordCamp London potentially. And I specifically went there, I spent the first six months of 2019 traveling to the communities that had told us that we had created the most chaos with merging Gutenberg. And just having y’all tell me what you hated the most about everything. And almost always the answer was, you might be right about the future of this software, and why Gutenberg needs to exist, and I just wish you had done it in a different way.

And so that’s what I wish we had done differently, is to do a bit better change management. Because all change, whether it’s a good change or not, represents a loss. And so if you cannot say at the start, this is great for where we are, but it’s not going to get us into the future. I think this is why we have to leave this point, and then I believe that this is probably the next point that we’re going to, help me find the way there. If you haven’t said very clearly, and with lots of confidence, why today won’t get us to tomorrow, you’re not going to get people to comfortably come with you into tomorrow.

We did do that work, and it was a lot of work. A number of contributors in Automattic, and in WordPress, and in other sponsoring companies, put in so much effort into training, and communications, and mediation, and just like listening. And I think that we could have done a little bit less of that, if we had done a little more proactive work, and just letting everybody know why we felt like WordPress needed to change.

[00:37:37] Nathan Wrigley: Yeah. If everybody working in the WordPress community was an employee, then you could distribute the memo, couldn’t you? You could just say, this is the intention, off we go. But you’ve got this massive diaspora. And some of the people, you know, some of them are paying incredible attention to everything that is going on. Other people are just, oh look, it’s been updated, I wasn’t anticipating that.

But I think about it a bit like a jigsaw puzzle, the whole project, but Gutenberg in particular. And it feels like now that we’re in 2024, it felt like there were just one or two pieces of the jigsaw puzzle. And we knew that there was going to be this complete puzzle. But now it’s got a little bit more fleshed out. The communication got better. Most people seem to be on board. Everybody can anticipate what power behind it is. And I feel very confident that that was the right decision. I think you’re right, it was hard to communicate all that.

Okay, we won’t stare five years into the future. Let’s go for a year, because that’s enough. What are you excited about over the next year in WordPress?

[00:38:29] Josepha Haden Chomphosy: So, this is going to be back office excitement. This feels like the year that WordPress, and its community, is going to like get really aligned on what we’re trying to do. Like, I feel as though we have enough people in the community, and enough really big voices in the community saying, we need to all just get pointed in the right direction, and everybody row in that direction. There’s a lighthouse, don’t hit the rocks. We’re going to do the thing. Like, we have enough people that are all saying that we really need to band together on this.

I think we’re going to be able to get that done this year. And I don’t really know what that looks like. But I do, especially like in this particular event, hearing the contributors, and how excited they are. And we had like 75% new contributors. I thought they said 35%, but everybody keeps telling me I misheard, and it’s 75.

Like, 75% new contributors. These are people who have never cared to come and do this, either because they didn’t know that the community existed, or because they were busy trying to get their own businesses set up, so that they had the luxury to contribute some time to WordPress. For whatever reason, regardless, 35% is also a giant number. 75 is enormous, but 35 is really big.

Hearing the excitement that people have around what they could do, if they understood what our goals need to be. People want to see the direction they’re supposed to be headed in, and that WordPress is supposed to be headed in, so that we can make sure that it goes a bit further, a bit faster. And I love seeing that because I agree. We would love to go a bit further, a bit faster, and see what is around the corner.

[00:39:54] Nathan Wrigley: You genuinely sound incredibly optimistic.

[00:39:58] Josepha Haden Chomphosy: And here I am saying I’m a pragmatic realist.

[00:40:00] Nathan Wrigley: It’s really not coming from a point of, you know, I don’t get the sense from you, that you are saying this because it’s a trope that you’ve got to give me. I feel that you passionately believe everything that you’ve just said. It’s an important piece of work that you’re doing. You are completely aligned with it. You sound like you’ve got real optimism for the future. That’s great.

[00:40:17] Josepha Haden Chomphosy: I’ll give you a secret. And it’s a thing that I wish I could tell everybody, and so hopefully you have all of the WordPress project listening to this podcast. So, you know, you’ve got a task. So I cannot pull together enough words to express how much I care about this community, and what they want to be able to do with a software like this.

10 years ago, I did not understand what a software like this means. I was just like, someone, quote unquote, someone out there is giving away a whole software for free, neat. I didn’t get it. And the more and more that I learned about it, the more and more that I just, it’s so much more than any one of us. Which is an amazing thing to be able to say about a piece of software.

And as I moved from, in 2015, to my role of managing meetups, which is what I was hired to do, all the way to 2019, when I became the executive director, and then also became the leader of the open source division at Automattic, my work changed so much in that one moment.

And the thing that I hate the most, is that I think that our community of contributors, and especially the ones that are not just replete with hours to contribute to WordPress. I hate so much that they will never know how much I care about their success. That was always my favorite thing when I was working with events.

To see people come back year after year, and not only be like, Josepha, I took the advice that I got at this event last year, and look, I have my business up, this thing is thriving. Not only be able to come back year after year, and like be able to celebrate what they enacted, with what they learned the year prior. But then also, to be able to say, at some point, I have all of this success, because of what this community does. And so now I’m going to be part of that community, so other people can have that success.

Those were my favourite, favourite, parts. And I miss working with events all the time, giving presentations to help people learn how to do this better. Whether this is like literally blogging, or running a business in WordPress, no matter what. I miss giving people that kind of information.

But also, I know that I can make a much bigger impact with this work that I have now. And the fact that the way that I have to do my work doesn’t let me be very clear with everyone that I love their journey. I desperately want them to succeed, and I desperately want them to succeed with WordPress especially, but like open source overall. Like, it really pains me all the time, that people will never know how much I care about that.

[00:42:47] Nathan Wrigley: Your enthusiasm is genuinely highly infectious. Amazing. So, we’ll just round it off. Firstly, for all of the hard work that you’ve done to get you where you are, thank you for that. In anticipation of all the hard work that you are going to do, over the next few years, again, appreciated.

I’m sure that your job, in many ways, is a thankless task. You know, you’ve described that you would like to be able to speak to everybody, and reassure them, that’s not going to be possible. But for what you’ve managed to tell us over the last half an hour or so, I really appreciate it.

[00:43:13] Josepha Haden Chomphosy: Well, thanks for making the time.