Mary Hubbard is the Executive Director of the WordPress Project and brings a rich background in ecommerce and social media to her self-described work as a product-focused “connector”. Mary joins Luke and Jonathan to discuss the open versus closed web, what the WordPress ecosystem can learn from platforms like TikTok, and the importance of digital literacy in a world of AI. Mary helps Luke make a new connection, Jonathan geeks out about the Art of Gathering, and birds join in from the Australian coast.

Transcript#

Jonathan:
Our guest today is Mary Hubbard. She’s the Executive Director of the WordPress project. Mary, for someone outside of WordPress entirely, like if you just met someone at a party and they ask what you do and you say you’re the executive director of the WordPress project, how would you explain your role to them? Let’s assume that they know what WordPress is, but maybe that’s it.

Mary:
Interesting. ⁓ So first I rarely ever say that I’m the executive director of I usually just talk about, ⁓ I always default back to product. And then since I’ve taken this role, I talk a lot about community. So I like to call myself the connector. So I say I work in tech and I like to connect things and people to build cool stuff. And so with regards to WordPress, that’s exactly what I speak to, and I actually talk about more of the span and the scope of WordPress, because most people who think about WordPress don’t know what it can do or how large it is and what it entails. It’s not just some CMS anymore. And so then I kind of geek out and get excited about that, but I usually refer back to just basic tech and geek out on product.

Jonathan:
That’s cool. One of the things I’ve enjoyed about ~ so for the listeners, I’m wearing a shirt right now that has a WordPress logo on it. I like going out and about and occasionally someone will be like, “oh hey, I know what that thing is over there.” And I’m like, yeah, it’s great to have that common point.

Mary:
I love spotting people in the wild. ⁓ So I’ve traveled around the world and often, like we all know, I didn’t work in the WordPress ecosystem for a few years. And so I would be out representing TikTok and see somebody with a WordPress shirt on or a WordPress hat. WordPress hats I see more than anything else. And it’s like, ⁓ I’ve been a part of that. I really like that. ⁓ It’s been cool. I never have the guts to go up and say anything, but I’m like, you know..

Luke:
Well, let’s talk about your time at TikTok. what was your role there? When you were there at TikTok, how would you introduce yourself?

Mary:
Yeah.⁓ so I was the head of governance and experience for North America. I was responsible for the end to end experience as well as all of the governance and launching TikTok Shop as a product. yeah, ⁓ so, so my journey is funny with TikTok because as most people know, I was at Automattic first and I was in England at the time. ⁓ And so I was working at Automattic at wordpress.com and I started to consult for TikTok Shop in England.

So TikTok Shop launched in England first. ⁓ And my history has always been building ecommerce platforms. So I’ve been a part of the majority of the ecommerce platforms that people use today. And so that was the kind of my stepping into that. And then I was asked to take over and launch it in North America. And so I moved to the United States and did that. But it was phenomenal. It was a blast and an amazing experience. I was employee number four. So.

Jonathan:
That’s amazing.

Luke:
Wow.

Mary:
You can’t see it, but I talk about this often because I think when you’re a part of something new, you always talk about the swag or what you got, what was the founders, what was it. And so when we built out eBay Motors, I had this little diecast car. We had all of this really cool eBay Motors and the product developed for that. And then for TikTok Shop, I have a bright neon sign and it was the neon sign we would use when we were promoting it. And so it’s like this legit old 1990s, like it looks like from the 90s old bar signs and it’s like TikTok Shop. It’s like, yeah, hanging in my office. I really like it.

Jonathan:
When I first met you, I was working at WooCommerce at the time. I had a community role at WooCommerce and you were over at dot com at the time. I didn’t realize until I got to know you a bit, like how much ecommerce that you’d had in your background prior to that. And then you sort of continued that. I’m curious, like how much has the ecommerce lens shaped you? Like how often do you see that still coming back in like the work that you’re doing today?

Mary:
Yeah, think it’s more about building cool things. So like ecommerce, even when I started at eBay, was never about e-com. I actually started at eBay doing a completely different role. I was doing content translations globally. And so I was working on the content field and how we would roll it out, which was all developmental rollouts. And then I just ran into my future boss on an elevator and we started chatting and I ended up in e-com.

Jonathan:
Interesting.

Mary:
I ended up on the business side of it. So I have expertise in ecommerce for sure, but how I apply the principles of what we build out, I think is relevant across anything we do, right? ⁓ And so that’s, it always comes back to product development for me. I look at the world through a product development eyes, just agile functionality, frameworks, project management, all of it.

Luke:
One of my lenses for the world is the open web versus the closed web, Or apps and iOS and Android and all of that sort of thing. And to me, I mean, when I think about TikTok, I only have the context for the negative things. I’m not on TikTok. I’m way too old for that. so like when I hear about TikTok and TikTok Shop, I’m going, man, that’s like the antithesis of everything I stand for with the open web. How do you think about that? Is TikTok Shop just a competitor for WooCommerce or is there more to it? Is there a bigger picture?

Mary:
Well, first I want to say that you’re not too old for TikTok. I think that’s a common misconception is actually TikTok is for the older folk now. It leans more towards millennials, millennials and Gen X. All the younger gens have already abandoned it for the most part. ⁓ But when it comes to TikTok Shop versus WooCommerce, I don’t necessarily think that they are direct competitors. They might be indirect competitors, absolutely. But TikTok Shop is forming an entire new type of interactive shopping. Whether you want to call it social commerce, unintended shopping, the idea of that is the next gen and future shopping itself. ⁓

Luke:
Wow. Unintended shopping is not something I’ve heard of before. It sounds dark.

Mary:
Well, it’s like, from a business perspective, I don’t think it has any dark patterns, but essentially it’s when you meet a user or a customer at the exact moment of the time they need something or desire something or would fill a problem or a gap, it’s right where it was supposed to be. And so I didn’t intend to buy this, but it solves a problem that could either speed up my operations, my daily life, improve me in some way, shape or form, and I didn’t know it. And that…that’s huge on TikTok Shop. Like the amount of small communities that exist there, like BookTok, HealthTok, things that people are educating themselves on that platform and just so happen to link out. And linking was still very prominent for WooCommerce with TikTok.

Jonathan:
I was going to say like the BookTok is actually a good example. Because for me, one of things I still love about going to a local bookstore is the curation experience, the things that I wasn’t looking for or intending to buy anyway, because if I was intending to I know where to get it. I can go to Amazon or I can go to my retailer of choice. But it’s the unintended things. And that’s the experience that I had when I’m not as active on TikTok anymore. But I found some really great stuff like like little niche communities of like, “oh, interesting”..

Mary:
Yes.

Luke:
And that’s a social experience. I’ve got you. I made the connection. Yeah, yeah, that’s good.

Mary:
Yeah. And it’s interesting too because lives are very much a social experience. And people do want to interact and we, society itself - social media and how we interact with social media as a society is changing and shifting. But as we move further and further into AI, the idea of you and me having a conversation or me dropping into a live interaction with you, your weight of a trusted individual become a lot more important over the next couple of years.

Jonathan and I talked about it at CloudFest, like I really believe that the internet and your own personal website is about to have its day again, because people and human voices are going to become much more important when the world is full of AI.

And very similarly, when it comes to a controlled platform like TikTok, you and me would have a relationship. These people feel like they have a relationship with those influencers, those content creators. And that platform has really flatlined what traditional celebrity is. ⁓ And we’ll continue to see it as algorithms shift and change. You’re going to continue to see an ebb and flow of more influential people, depending on the area of which you are.

Luke:
Yeah. Mmm. This is fascinating to me because it’s like a confluence of two things. It’s like putting two ingredients together that you didn’t ever think, they’ll taste good together. And then it’s a surprising result because I guess I’m one of these people. And I think ⁓ a good chunk of our audience are people who - you must’ve come across us before - the social media abandoners, the people who are like, no, they’re the bad guys, right? Facebook, TikTok, Instagram. I wouldn’t use those products. I’m all about the open web. I’m all about open ecommerce and I wouldn’t even want to use Shopify for my own store. You know, I want to do something open.

And then at the same time, you know, you’re talking about our bread and butter blogging and the personal website, which I’m passionate about that. And you’ve brought those two things together. Help me make the connection there because I love blogging. I think it’s an art. I think it’s personally really, really helpful to, to get your thoughts out and it builds community. If people would only just use RSS readers, youw know? But at the same time, it doesn’t seem to be thriving. I hope AI changes that. But how do you make this connection back to like the influencer style thing?

Mary:
Yes. Well, how I put it all together is that I don’t think it’s thriving. I would question why. Why is it not thriving? Because who’s controlling your access to the web? How are people finding you? And now it’s become an ad-based thing to get your content, to get your information out there. It has been served. And it’s a multi-billion dollar business. I think it’s like a 200, 300 billion dollar business just in ads for Google alone to try to get your content up and running.

People now, or people have been taught, Google has become a verb, right? I’m going to Google it. And so people have been taught to go there. But what people fail, the masses fail to recognize is that that is a version of the web. And it’s not the web. You as an open source person is like, this is a version. I could get it through all these different search engines. But most people don’t. They go to Google. They get it. And so how AI is going to start changing that game is people are going to skip that search engine, which means all of society is going to be shifting and changing on what the next best thing is and how we access the open web, how we access what truly is.

So will another platform emerge? Will another way to access this individual content come out? Who’s to say? I think, ~yes, I think that human experience, human thought, whether or not something is going to be coming from you as a human will start to become more more valuable. How it’s accessed will become a product. What that means will need to be built out.

And like, and it’s - I lost my train of thought when I heard the birds, but even more so, ⁓ I’ve referenced eBay a few times already and I usually do when I’m talking about this in a theory, but I want to tie it back to TikTok for you in two ways. When we went out in the 2000s and we started talking to businesses who didn’t want to come onto the platform and their concern was, I don’t want to come onto the platform. I’m an individual business, you’re just going to take my traffic.

It’s like, well, we already have your traffic, dude. We dominate in traffic. And so you should use us as a platform as well as create your own identity. So you have your identity on the web. You know, you’re a brick and mortar store. You are creating trust with me and we are in access use eBay as an access point. Right. So you start to see that with the open web. And when it comes to TikTok, for example, when we launched TikTok Shop, I kept telling the team over and over again, we are training a society on what to do with this.

Luke:
Mm.

Mary:
You heard me say this is unintended shopping, it’s social commerce. This doesn’t exist in the United States, but it’s huge globally. Why? Because our society, our customers have to be trained on what it’s like and what a good experience is to, to interact with an influencer, buy a product. They have to understand what that means to get the product here, how to surface the product up correctly. There’s a ton of things that we are learning and teaching at the same time to move society in a certain direction. And now TikTok Shop is the dominant player for TikTok. It’s no longer the global business.

So like when you think about those two things and where we are with AI, it’s the same. We as open source people in WordPress are going to start to need to direct society on where to go and a whole bunch of products to short fill that will emerge and die. But that doesn’t mean that they weren’t successful in that moment. They served a purpose, but but technology moves very quickly. So you’re going to see this. You’re going to see these individual access to the web.

You’re going to learn and discover new monetization mechanisms. And those monetization mechanisms will likely die out as society lands on where we’re comfortable until the next big iterative shift. And you’re seeing that across the board.

Luke:
That’s amazing. I mean, it’s also like a beacon of hope. If I could sort of reframe what you said and tell me if I get some of this wrong is the open web is really the core of the internet. And you have trends come along. It’s crazy to talk about Google like a trend, but Google came along and it provided a centralized location.

It’s a centralized search and that’s how people would access the open web. And then we had this social media revolution and suddenly we had all of these different social media players. And you could even say that there was a less centralization if you think about people trusting specific influences as a range of influences that are then people’s access points back to the open web.

And as the culture maybe shifts away from some of that or maybe not, but certainly the culture is shifting more towards AI. And once again, we get this same thing happening, which is people interact with one product. Maybe right now it’s ChatGPT, who knows what it will end up being. And that at the end of the day is serving as a platform to access the open web.

Jonathan:
This is reminding me as I listen to you guys, I don’t know if you had this in Australia, Luke, or if you saw this Mary, there was the Home Shopping Channel, like way back in the day. And my mother would watch that and I found it kind of annoying, but also fascinating. And the form of interaction back then was that you could call in, but you couldn’t talk to the influencer, if you will, that had the wares. Whereas today with TikTok, you were able to get this. I can see it as a much more personal experience that you can have that gives that sense of connection to folks.

Mary, one of the things that caught my eye on your LinkedIn profile, you mentioned some of the books that you’ve been reading. And as I’m listening to the two of you, one of the ones that stood out to me was the art of gathering. I find myself thinking more, even as I get really excited about technology and how we can use AI.

I am finding myself thinking even more about the role and the value of human connection and relationship in this context. And The Art of Gathering was a book that stood out to me. I really enjoyed it. It’s been a couple of years I had to refresh myself and as I was reading back over some of the notes from it, I like, okay, yeah, this still resonates strongly with me. I’m curious, did you get it, I can’t recall, had you finished the book or did you just started it or?

Mary:
No, I’d finished it. But again, it was one of those ones that’s a reference, a referenced book. So like, it’s ~I feel like very similar to what you were just saying. It’s one of these things that you somewhat go back to, depending on the conversations that you’re currently having. And, you know, I think I just come off of Work amp Europe, I’m thinking about why we gather, I think about how we’re designing these, we’ve had a lot of meetings there, a lot of conversations, like, what does it mean, what’s the purpose of it and so it was really more like thinking and reflecting on that.

Jonathan:
So to recap for those who haven’t heard it and for your benefit, Luke, some of the things that at least stood out to me in looking back - and you’ve got it fresher than I do, Mary - is this idea that gatherings should have a purpose. Don’t confuse like a category with purpose. Like it may be a birthday party, but it can still have a clear purpose. And often there’s an implied purpose, but not always. ⁓ Like it’s sometimes people aren’t clear on what that is. The host of a gathering should be proactive and not passive.

There’s some interesting ideas about how to open a gathering with something that gets their attention and how to close it with intention. Like what’s the thing that you want to leave them with? And then one thing that stood out to me too is this idea of seeing gatherings is almost like this temporary, like alternate world, or this experience that you’re inviting someone into. ⁓ So yeah, does that match what you recall, Mary, or anything else stand out to you?

Mary:
It does. It does very much so. And I think that we use these a lot. We use these a lot with meetups. It’s the intention. I think a lot of the intention has to be set. Opportunity for vulnerability, opportunity for stillness. And I think we, think in, especially with WordPress in our day to day lives, we don’t open up the space for the stillness aspect of it.

We’re very quick, we move, we want to push things forward. There’s a lot of Slack pings. How does that work? And so like gathering together with intent, opening up, setting the purpose of this meeting, allowing people to have constructive conversations and then reflect and taking the time. Why are we here? What is this for? ⁓ Those types of things and how we can get the most meaning out of it, really.

Jonathan:
That’s so interesting. If I think back over my, I’ll use WordCamps and Meetups as an experience for me personally, and just think about some of my community roles. When I attended Meetups, what I’m thinking as I go, and maybe there was probably a lot more behind the scenes. I heard about this book from Andrea Middleton, who was a mentor of mine, and she was involved in the community side of things with WordPress back in the day. When I would go to a Meetup, for me, the implied intent was this, we’re gonna help each other.

And so you’d show up and someone’s got a problem and I’d jump over there. I had a question and I was usually helping someone else with theirs. But I genuinely like enjoyed that. And it’s like, we’re the purpose was this implied, like we’re going to help you have a success with WordPress. That’s where you’re going to win. And for me, that extended to meetups. That felt pretty clear.

With WordCamps, at least for me, was always a little bit less clear and more of this like it’s going to be what you make of it personally. And for me, I found this enrichment from like I want to connect with other people. So I brought my own like intention and purpose to it. But it wasn’t but like so I’ve been surprised sometimes people will express. Let me put it this way. Word camps have always been a win for me in that regard, because that intention was the my clear like it’s I’m not going to be picky about the sure I can care about the topics that are covered or whatever. But the intention is to connect and expand my horizons to meet with folks.

Luke:
Hold on, what about the catering?

Jonathan:
Well, sometimes the catering’s amazing and sometimes it’s somewhat to be desired. whereas I think some of the criticisms and concerns I’ve felt is it’s occurring to me that those could come from someone else had a very different expectation. Whereas with meetups, it tended to be a lot clearer like what that is. We’re here to help each other. We’re gonna solve some problems and everyone walks away and it’s clear what to do next.

Mary:
Well, and what I think too from the meetups that I’ve experienced is that they actually do take time to just bond. There’s just a lot of this. And I think that that human level is very much needed. we tend to, we experience things very transactional, but we’re all very different. And we experience the world very different. And I think that was one of the best things about meetups is especially when you’re when you’re a geeky person and you’re behind a computer like your communication style might be short you know you’re you’re not picking up on body language there’s tone and then when you get to interact with people you kind of feel that vibe right you understand how to work with people and that opens up a lot of I mean for lack of a better word it allows vulnerability it allows you to see people as people and then understand how to work better with them and I always thought that was great and I think that

That is deliberate. That’s a deliberate action to try to go and interact with people at something like a WordCamp to understand how your communication style is, meet people face to face, be very mindful and focused on that, which shows a lot of value, I think. There’s a lot of benefit of just getting to know people and talk about absolutely nothing. I think it’s great to talk about nonsense because those are passionate things.

When we were at CloudFest, we sat on the couch for… an hour talking about random stuff, but then all of these passionate ideas come out and you see what motivates people, how people are driving forward. It’s great.

Luke:
Yeah, I guess we call that the hallway track, don’t we? And I’ve recounted this story a few times, but it, mean, it’s really stuck with me. It’s really, really made an impact at WordCamp Sydney, the previous WordCamp Sydney. I met a whole bunch of people there who I hadn’t seen since before COVID because hadn’t been to WordCamps, you know, it was the first one back and it was so good to see all of these community members.

And I said, so what are you doing these days? And I reckon half the people I spoke to said, I actually don’t work in WordPress anymore. And I said, ⁓ that’s interesting. Why are you here? And they said, well, WordCamp’s not about WordPress. WordCamp is about the community. And this is where I’ve found my community. I thought that was beautiful.

Mary:
I think that’s beautiful too. And I think we should figure out how to welcome them back and engage with them. Right?

Luke:
Yeah.

Jonathan:
Yeah. Mary, one of the things that as I’m listening and thinking about this, one of the things that I’m curious about with this idea of meetups and WordCamps and then the social gathering, this art of gathering, it’s very much as emphasis on the human connection in a world where we’re increasingly like focused on the technology and the way that AI can help or not help and these things like how as you’re coming right off of reading that, did anything stand out to you about how tech or AI might impact what it means to gather or or what that looks like?

Mary:
I mean, nothing specific to AI. I don’t know. I think society has shifted since COVID where we were forced to kind of be in the tech zone, but tech’s going to make it a lot easier, right? Like technical, oh, go ahead.

Jonathan:
When I say AI, let me offer it this way. Like I’ve found that the value of human connection seems to be going up. At least for me, like this emphasis on having an in-person connection, to me at least, offers this opportunity to, as we have even better technology that can do things for us. There’s a greater value in knowing that there’s a real human, so to speak, like on the other side of it. So that’s more of like what I meant. I’d hate to think that we would use it. I mean, I guess you could try to use AI to like represent you or something, but please don’t.

Mary:
Yes. It kind of goes back to what we continue to speak about. There’s often this fear when I start to talk to my friends or family around AI and the future of AI or when I’m questioned about it, it’s like, it will facilitate connection. AI will handle logistics. It’s not going to be the connection. Like smart tools are going to help you interact. It’s probably help you translate. Like there was a great product I used, Lark, that was doing real-time translations. I keep talking about this because it’s an internal tool, you can use it and subscribe. ⁓ But I think this is very powerful tool, but essentially we would dial in and I’d be speaking in English, you might be speaking in German, and in real time the conversation is transmitting. And it’s picking up not just translations, but contextual translations.

Jonathan:
That’s amazing.

Mary:
And so we have the ability in real time to speak to one another, understand, to get to real time understanding very, very quickly. That product is called Lark. I’ve talked about it in WordPress, but today it’s just not as important or it’s not as prioritized to get it. But it can’t replace the human action, right? And it can’t replace social norms or social context. So it’s going to be increasingly important to have one-on-one time.

Jonathan:
Well, that to me is such a great example. I haven’t thought about it in a bit. I love, like I speak a decent amount of Spanish and I love the Spanish language. And when I go into a Spanish speaking country after a short period of time, like I start to shift some of my thinking.

And I could see so much power in that ability to like take a language that I have no context for to be able to go and have a meaningful human connection where technology and AI is a good example of that. need that the contextual, the context clues are part of what enrich the conversation. It’s not just the direct translations, right? That can allow you to have a meaningful connection where you wouldn’t have had it otherwise.

Mary:
Yeah, and we talk about it, we keep talking about it in ways of like, AI will replace engineering, it’s going to replace this, it’s going to replace this, and it’s like, it’s actually not. Most everything we do is going to be AI assisted, it’s going to be tooling, it’s going to help us be better humans, if we use it right, and we govern it correctly, but this would be how we would shape the future of and it is, it’s ours to shape. think these are the types of conversations, it’s going to be tech plus human.

Tools will make and expand what’s possible. And that’s how you need to, that is the mindset you should go into these types of conversations in. Because with every fear bait around, it’s gonna, we’re gonna do this, we’re gonna do that, there’s also the other side, right? There’s the other side of actually, it’s going to help people who are dyslexic be able to write.

It’s people who cannot read very well, going to help them learn to read. There are so many great things that are going to increase connectivity at a human level and bring people up. And so we need to put that headspace on when we think about it.

Luke:
So do you have any ideas or guidelines or suggestions on how we can use AI, right? do you know of any wrong ways to do it? Do you know what I mean? Like, this is something I’m thinking about a lot because I mean, for me, about my children, you know, and about, you know, any, anyone who I have the privilege of teaching in like a home education context.

Mary:
I mean… ~Yeah.

Luke:
I’m often thinking about, well, you know, should AI write this essay or not? And it’s not always super clear.

Mary:
Mm-hmm. I mean, again, we’ll go back to product. We had talked earlier, right? We talked about dark patterns. Dark patterns exist in everything we build. They will exist and do exist in AI. And so understanding what that is, how design choices can be manipulated, how it can put you into an endless loop, how it can shift or make large amounts of people think in a certain way, it matters. It matters a lot. We need to understand.

And what would be that ethical standard, what is ethically shady. I think a lot of these conversations are happening, but algorithms don’t have values, right? If you’re using something that’s algorithmic, I’d recommend you adjusting it and shifting it often. I actually was at Disney World with my children. We were on the waiting in line with Snow White ride, and my daughter started interacting with this other little kid. And so, of course, you know, there’s an old adage like, “we in this line together”, right?

Like, you start talking to people and, ⁓ she was asking me questions around TikTok’s algorithm and whether it was safe. So my advice to parents, like, first of all, children shouldn’t be on anything that’s not monitored flat out, flat out. My children aren’t on TikTok. My children aren’t on any of that, but, ⁓ you have the ability to reset your algo instantly on your screen. You have your ability to change your algorithm. You have the ability to put in blocks. You have the ability to not log in. You are seeing as only a minor’s view, right? So there’s a lot that you could do to control that. And you should be the advocate of it.

Jonathan:
Well, was, that’s such a great example because if I think back to what I really loved about my TikTok experience, I went into it with that mindset that I was going to quickly, I wanted to see how well it would do. And it did a great job based on my selections and a couple of searches to quickly give me an algorithm that I valued. I liked to see standup comedians. I had interest in particular like types of, like particular games that I enjoyed playing. And within a short period of time, it was giving me more of that.

And if I thought about this through the lens of like, I’d want my kids, I’ve started talking, my oldest is 15, I’ve started talking him about like the Instagram algorithm. And like, I want him to understand that, because it’s like, it’s not inherently bad, at least from my point of view, but the challenge is when you’re not aware of what’s going on, and then it’s just feeding, you end up getting into this little bubble of your own creation without realizing that you created it.

Mary:
Well, and let’s take a moment to recognize where we fit in, let’s say, like the generational scale, right? ⁓ We experienced this, like Zillennials, Gen X, Millennials, Elder, geriatric ones. ⁓ We, that’s us, right?

Jonathan:
That’s you, Luke.

Luke:
Back in my day. Yeah.

Mary:
But we also experienced, right? You had access to the free, you had access to the open web, probably way too young. And the same fears existed. Like the same, I mean, right? Like you, you just ran amok. And we saw things we probably shouldn’t have. Right? Yeah.

Luke:
Yeah.

Jonathan:
That’s fair. That’s fair. At 13, I had a wares site that was big online, my mom had no idea what I was doing online.

Mary:
And because the technology far surpassed her, my mother didn’t even have the ability. She’s like, what are you talking about on the computer? imagine, and then even think about the technological changes that you went through just in your high school years, from junior high to high school, and how you managed that. And of course, how you looked up when they were questioning, like, you don’t know who you’re talking to. You don’t know, be careful of this. Who’s creating these sites? these concerns are amplified with AI and algorithms.

But the principles remain the same. There are dangers to these things. There always will be. Technology has an aspect of that. There’s shadow and light in all things that we do. ⁓ And so I think our generation is very uniquely positioned to be that overstepping guardrail and then having those conversations as well. But we are in a very unique position for that.

Jonathan:
I like that.

Luke:
Especially since it feels like our generation understands the technology at a more fundamental, more foundational level than most other generations, younger and older, right? We’re unique in that sense.

Mary:
Yeah, okay. So I read something yesterday that I think is funny. And I can’t tell you where I read it because I read every night and then I go through things very quickly. But this is what it was. And it was talking about how you ⁓ the reason that is the case is because when you first received a computer, right, you went from like DOS to Windows, you these PCs, and then in the schools, you had all of these PCs. So you fundamentally understood the hardware and the software and you had and they weren’t very user friendly.

So when something wasn’t working, you debugged it, worked through it, you were trying to figure it out. And now things are so user friendly and so user intuitive. You’ve got younger generations who can’t actively debug things. Right? And so they’re like, Gen Z has now, and I don’t want to stereotype and like be like sweeping generations, but this is what the article was talking about. It’s like the younger generations have now actually matched the older generations.

Jonathan:
Right? Right, that’s a great point.

Mary:
And it’s the same theory, it’s because it’s not because they had access to the technology or even more advanced technology or different types of technology. It’s the scale at which technology shifted and changed. It was that adaptation that enforced and reinforced the fact that you can move within technology means you understand technology at a different level. ⁓ And I thought it was hilarious, like on the nose, right?

Luke:
Yeah. And, but then the question that comes out of that for me is how much does understanding the platform, how much does understanding how it works influence your ability to think critically about the way you interact and the content you receive through that platform?

Mary:
Well, and I think it’s different when you’re thinking about a software platform and the hardware that accelerates it. ⁓ You can understand how the platform works as a child because you want to be a YouTuber, and you can understand how to make YouTube content viral versus what they’re doing on the dark pattern side of that, or even have the emotional maturity or intellectual maturity to understand the effects of that throughout your life, right? Which is where parental guidance and maybe governmental guidance should come into play. But yeah, absolutely. From a platform perspective to the unique understanding of software and how software is built or how hardware is built.

Jonathan:
It’s interesting to me, I wanna pull on this thread for a moment of like what I’ll describe as the counterintuitive user experience or the ramifications of it. Something you said there, Mary, like I think it’s partly because it was so like hard to use. You’re right, like when I look at a computer problem, like I immediately go into debug mode and I remember at a young age, I noticed that differentiated me from the older folks around me is it didn’t scare me. I wasn’t worried about something breaking.

Luke:
And you broke things and that’s okay.

Mary:
And you broke things. You were probably the person who caused it.

Jonathan:
I was willing to go in and like try things and like tinker and figure it out until I landed on something. And I did break things. And I looked up, sometimes that was the case. And I would look it up and I’d figure out how to fix it. the other day I was helping someone update their DNS and I brought the same skills in. Like something broke and then we fixed it and it was this whole sort of series of things. And it’s almost like, if I think about people who are interacting with ChatGPT and tools like it, like there’s something.

I think it’s rightly winning because of this emphasis on like user experience and creating something that just gets you that doesn’t ⁓ slow you down with all the details. It gives you a good experience, but there could be a counterintuitive side effect of like you not learning how to ask those more critical questions or not being able to debug something or not being aware. Like when I’m interacting with a large language model, I feel really comfortable using all my debugging and like exploration and curiosity skills to keep at it. And the people that I’ve seen have success have a similar thing, whereas others I’ve seen just get frustrated or it didn’t do the magic thing that they thought it was gonna do. And it’s not that I could explain to you exactly how it’s doing it, but there’s something about the curiosity and that background in troubleshooting that to me is a byproduct of poor user experiences.

Mary:
Well, but it’s also why we continue to talk about how it’ll be more more important for you to learn how to prompt. Because prompting is critical thinking, right? It is actually using it as a tool to go back and forth and saying, okay, and also how you’re interacting with it is just a curiosity of thought. Like you’re like, okay, hold on, this isn’t working for me. Let’s go and go and go and go, which might be a personality trait, but also where we need to push people to start prompting effectively. Like you should be asking these things. Yes, it’s how you will learn it. Exactly.

Luke:
It’s a literacy. Yeah. Yeah. In the same way that like learning the YouTube algorithm, which is a great example is you become literate in what works and what doesn’t and how YouTube is trying to convince you to watch the next video or whatever. And there must be a literacy to using social media that obviously I’m completely illiterate in.

And there is a literacy to being able to interact with and a chat based large language model, how you prompt it and things like that. I’ve got a whole bunch of theories on, you know, Bloom’s taxonomy and higher order thinking and lower order thinking that probably don’t apply to the, in this podcast that may be more educational, but yeah, we’ve got to learn. I agree. We’ve got to learn how to interact with these sorts of models.

Jonathan:
The difference between a child or someone, it could be an adult pulling it up and like make game for me and they might be impressed with the output it could be a good thing versus like having confidence in what’s possible and then carefully like scoping out like what you’re after and being able to like write the specification for it which is the the critical thinking part right?

Luke:
Right.

Mary:
But it’s back to what Luke said, right? It’s actually understanding how, even at the service level, how it works. Like AI can hallucinate and give you false information. It can jump to conclusions. Even just understanding that it can will actually have you prompt and continue to ask to try to, okay, show me where you got this information. I don’t understand that. and interacting in that level will start to influence and change it. ⁓ And I think that that’s going to be.

It shows a different form of critical thinking. think that there’s a literacy problem in the United States. I should say, social media has probably helped exacerbate that. But being able to see or understand what’s real or not take something at face value is critical thinking to actually debug something in real time when you see a title of an article and then read that article and you’re like, wait, hold on, this isn’t what it says at all. So I think all of this will start to work in in a very different way because now, now, you know, you are typing or you’re speaking into this and it is, there are these different ways that even our brains function to help us learn and grow and interact and commit things to memory and thought. ⁓ I don’t know, we’ll see. It’s just very philosophical, right?

Luke:
I’d love to actually just come back around to a point you made earlier about bring it back down to humans, to the human level. And you said something earlier that was, I don’t know, it caught my attention, which is that maybe it might just be the case that with all of this AI, we seek out and value human written content or human designed apps or human made drawings or things like that.

My son, you know, he, loves drawing. He wants to be an illustrator and he’s completely frightened about, this even be a job in the future? But it sounds like you’re saying that maybe it might be even more of a job than it is now.

Mary:
I believe that it will. People aren’t making bets right now on it because they’re too afraid to see where society will go with it. However, you can go into large philosophical conversations around what is art. You code, code is poetry, right? This is something that we believe is true art. Who else in the world does?

So it becomes a point to where a person has something in their mind, an AI helps them put it into paper in an artistic format that they could have never done before. Your son’s an artist and draws and now feels that he might not be able to be an illustrator. AI, even if you look, I could spot an AI image from a mile away, right? Most people are learning. It’s going to get more more intelligent, sure. So, what is art? Why are there certain people paying 20 million for a painting? They see it as valuable, they see it as something that moves them.

Is it artistic because it was drawn by a human or is it artistic because it makes you move? And I can’t answer that for people. You’ve got digital printed art all over. You’ve got mass produced art, right?

Jonathan:
What I’ll offer as a qualifier for me personally is effort because for a human we have limited time like we’re finite, right? So I place a premium on the effort the time that was invested on behalf of someone else So the artists I don’t actually care if the artists use What tools that they choose to use but it’s the effort that they put behind those tools because the the prompt of make nice art To me doesn’t hold much value.

But someone taking a bunch of time to carefully write a prompt that produces this output. It’s the effort that I personally value and similar when people are reaching out to me like sure we all you can get people I don’t put much stock in low effort like cold outreach every now and then someone reaches out where it’s like clear that they put effort into it and they were paying attention. I have grown at least to place a value on human effort.

Luke:
Were they paying attention or did they have just a really good AI prompt?

Jonathan:
Right. Well, I’ve noticed the prompts are getting, I’ve noticed that the cold outreaches I get are getting a lot better because they’re using AI, but I can still tell. Like I, I’m like, no, you just, missed it.

Mary:
They got an dash and it’s too long. AI.

Jonathan:
⁓ I feel bad for the people who use em dashes actually because yeah.

Mary:
Yeah, it’s like no more. Yeah, no more man. I’m the key. I pause so much thinking I like I continue these sentences and I’m the queen of like parentheses and commas ~ it’s like my jumbled thinking is and so then the em dash. I’m like the Oxford comma queen and then the em dash entered the scene, right?

Luke:
Yes. man. High five for the Oxford comma.

Mary:
High five! I’m like, I can’t use en dashes anymore because it’s just and to me it’s just because the way that I think it’s like I have four thoughts in one and I try so hard to get it out that it’s just, you know.

Luke:
Yeah. Use the space dash space. That’s what I switched to.

Jonathan:
Yeah, I just use the em dash even more.

Last question for me, last thing I’m curious for your thoughts on. So if I think about social media as just a broad category, and I think about my experience, I don’t find personally much value in Facebook anymore. I’m still on it to occasionally contact people, or if I occasionally wanna see what’s going on with family that I haven’t talked to in a long time. To kind of just keep an eye on some interesting like conversations, people that I follow and I’ll interact with folks there.

One thing I’ve been surprised by, a couple months ago I got pulled into a group chat on iMessage. ⁓ Luke’s in it and ⁓ a few other folks that I knew personally before that happened to be in it, but there’s folks that I’d never met in person. And I got back to having this like, ⁓ what I would call like this more akin to like this IndieWeb, this small group experience where…

Mary:
The AOL chatroom.

Jonathan:
Kind of like an AOL chat room! All the way back to that and I’m like I actually find this valuable because if I go on to Facebook I’m not getting that anymore. It’s not a like sometimes you just want some other humans on the other side of like hey I’ve got a question about something or hey, I did something cool today and I’ve been surprised at how much I’ve actually valued that small group what I would describe as like a social media esque experience. I’m curious if you have any thoughts on that because I think part of it is

These big things, maybe this is part of what was so interesting about the algorithm ⁓ and experiences like TikTok is that it gives you something that feels much more personal and curated. ⁓ I don’t know. It’s something I’ve just been thinking more about lately.

Mary:
I’m not on any social media, and I’m passively on TikTok, but I use TikTok as an entertainment platform, not as a social media platform. ⁓ So I don’t think that those platforms have value. I don’t think Facebook has value. I think interconnectivity is exactly what you were saying. So if you have my phone number and you text me and we’re in these conversations, I much, I appreciate those much more. I think the platforms are there for a purpose and the majority of the people I know who are still on Facebook, it’s because of what you had just said. Oh, to catch up on family, to see photos and really? know. Like how, you know, it’s like long lost cousins. I don’t, I do see people just going back. There’s something to be said about how overwhelming we all feel. we are overwhelmed with the amount of information we see on a daily basis.

Like with the amount of context, how easily accessible, like I don’t think that we were meant to be so accessible to everybody all the time. ⁓ And then there’s, we’ve somehow created this need to respond immediately and bringing it back to these books, right? Like there’s a theme in all of those books about stillness and like just being in the moment, understanding that this is the moment, understanding that there is grace in that moment.

Because just because you have a hundred Slack pings doesn’t mean that you should respond to them all.

Jonathan:
That’s awesome. I love that. ⁓ Mary, are you going to be making it out to WordCamp US?

Mary:
I am gonna be at WordCamp US. Yes, my first one. So I’m excited about it.

Jonathan:
Is it really? Nice. That’s awesome. I enjoyed it a lot last year. I’m looking forward to it again. It’s driving distance for me. So it was a, I’ll make a long road trip out of it. I’m quite looking forward to it. No, it’s a little bit further.

Luke:
Not driving distance for me.

Mary:
No. But to be fair, everything’s a flight for you. ⁓

Luke:
That’s right, yes.

Jonathan:
Yeah. Even WordCamp Sydney is a flight for you.

Mary:
So, yeah, it’s always a flight. Now, I think WordCamp US is gonna be great. I highly encourage everyone to come to it. They’ve got some great speakers. The organizers are doing a great.

Jonathan:
I’ve been really impressed with how it’s coming together. Awesome.

Mary, thank you so much for taking the time and sharing your thoughts and perspective with us. I enjoy this a lot. If anyone does want to reach out, what’s the best way to get in contact with you?

Mary:
I mean, I’m on Make Slack. You can reach out via email. I do respond, but like I just said, I tend to not get overwhelmed, so I do respond. I get through them.

Jonathan:
That’s awesome. I think we can all take some inspiration from that. Thank you for sharing your time with us, Mary.

Luke:
Thanks, Mary.

Mary:
Thank you. Take care.