Follow John Maeda’s career trajectory, and you can loosely track the shifting zeitgeist of the design industry. A student at MIT, Maeda went on to teach at the famous and experimental Media Lab, where, as the internet was starting to take shape, he found ways to get designers and engineers to learn each other’s disciplines. Just as design with a capital D started to be seen much more widely as a professional career path, and not just an artistic one, Maeda left MIT and became president of the Rhode Island School of Design. His mission there was to expand on the university’s traditional notion of design, bringing in more focus on innovative tech and arts. 

In 2014, Maeda moved on to become the first design partner at venture capital firm Kleiner Perkins Caufield & Byers, where he threw his weight into fostering a new cadre of startups that employ service design, experience design, product design, you name it, as a competitive business advantage. He’s remained at KPCB as an advisor, even after departing in 2016 to take on the newly-created title of global head of computational design and inclusion at Automattic, the open-web publishing company that runs, among other things, WordPress.com.

When I asked Maeda for an interview for 99U's "Hurts So Good"-themed magazine issue, Maeda wrote back. “Maybe talking about the time I tripped at 5 a.m. jogging on El Camino Real and broke my arm and face? It is the key incident that made me focus on design and inclusion matters. I can explain why…” Intrigued, I agreed.

After all, if something has Maeda’s attention, it’s a good idea to follow his gaze.

The last time we spoke, you had just assumed your new role at Automattic. You were actually so new that you were still in a sort of orientation – which, for all new hires at Automattic, means spending a few weeks answering customer service requests. I can hardly think of a pain point more notorious and acute than being on the line with customer service. Did it feel like that at the time?

I realized in my first week that I was helping to solve problems that were more like fixing flat tires. Where does the help menu go? That kind of thing. You get a lot of questions about menus. Do I have too many? Does this look good? I guess people expect some kind of aesthetic response. There’s a bug, or there’s a misspelling – technologists would get rid of it; say, “I fixed it.” That’s how they fix the world.

But as a designer, I realized that I had to understand where they wanted to go in the car. I could help them solve their tactical problems – the flat tires – but if I could figure out where they wanted to go, I also addressed their longer-term strategic opportunities. I remember talking with a woman who was outside of London, and she had a dream to succeed as a parent blogger, because she wanted to talk about this new baby she had – challenges and tribulations about it. And she wanted to get sponsors, like from the local candy store. That’s hustling. For people like her, who want to do something different, people aren’t scrutinizing your menus – they’re looking for information about you. So, how I can help you do that became the question.

Was that the main takeaway?

It’s been part of my changing perspective. Some of this started in earnest a few years ago, in Palo Alto. I was jogging on El Camino Real. I used to stay in Airbnbs and take Ubers everywhere, to just experience living in this sharing economy. So I left the Airbnb and went jogging, and somewhere my foot caught onto something – the sidewalk. I remember seeing it coming at me, and I landed on my face and arm before realizing that my arm couldn’t move, and my face was bleeding. I had, ironically, just published an article on Techcrunch about health tech.

That’s very real, corporeal pain.

I was like, “I’m a piece of flesh on the ground. If I pass out, will someone find me? Where will I go? I’m staying in an Airbnb; I don’t have neighbors who know me.” Eventually, using lawns to lie on to take breaks, I got back. I took an Uber to the hospital, and they gave me a clipboard, but I couldn’t write. They said you have to write something. The doctor finally shows up and asks if I can move my neck, and he says, “Wow, you’re lucky.” Then an hour later a nurse comes in. He says, “I hope you were wearing a reflective vest. You could have been hit.” So I had these two moments of gratitude, of things that could have been worse.

But still, by having a broken arm, travel and work get really hard: putting stuff on an airplane; I couldn’t type as fast. That’s very minor, but it was a catalyst. It made me realize that I like advising companies [at KPCB], but maybe I should actually do something. Work in a company instead, and if I do, I want to advance this kind of thinking in the space of technology products.

John Maeda photographed by Julia Hembree.

"This kind of thinking” meaning inclusivity in design?

Right. In Silicon Valley or New York, you have a lot of access. People who are advanced in the technology world; they sound like they’re in the ivory tower. And I’m from the ivory tower, what with MIT. The reason that inclusive design is important is because of computational design. It impacts everyone; it’s not just technology for technies. So what can I learn from a lot of people who we’ve ignored because we don’t think they are Flipboard-able?

Is that what inclusive design means? It’s become a hot, buzzy term to use lately. That’s something that gets discussed in a really good interview that Mark Wilson, at Fast Company, recently did with Microsoft’s Kat Holmes, who brought inclusive design thinking to that company.

I think if you follow what Kat says in that interview, she says it’s a process and that the first step is to recognize exclusion. How do we find exclusion? It’s by being in environments unlike the ones we’re used to. We’re talking about pain, and I think that pain can also be read as a problem. And designers are problem solvers, so it’s important that they be in situations where they see a problem and try to understand it.

What does that mean, exactly, at Automattic?

There are people using Automattic’s services to try and earn $1 more a month; that’s a big deal to them. They will be psyched. A lot of my work has been to put a spotlight on people who want to earn online. Which, if you come from the blogging world, there’s an older belief that it’s about freedom of speech and saying what you want to say, and you don’t have to make any money. But working with Hajj [Flemings, a brand strategist and design entrepreneur in Detroit], I’ve learned that there are so many people who want to earn online.

One year ago we made it easier – this sounds so simple and obvious – for anyone to take a payment off their site. In the system, you just add a payment button. It seems really obvious, but it was just perceived as something someone didn’t need. Because if you look at any Silicon Valley system today it’s about the likes and the comments – that’s the measure of engagement. I think that’s been the dominant thinking.

Back to what you said about being in environments unlike the ones you’re used to: Is that something you’ve taken to doing?

Just in the job, in getting to know customers better, I think I have. It got me really excited; I was chatting with people whose background, I just thought, “Oh, this is neat. I don’t meet someone like you every day.” I’ve also met more people who aren’t necessarily a part of this really old technology, of communicating on the web. I might have five websites. But many people don’t have their own home on the internet; maybe they’ve only had a rented home, on a social platform like Facebook. So that’s different. 

But physically, too, I’m addressing how ignorant I’ve become. I’ve been forcing myself to go to places I haven’t been to. Especially when I met Hajj. He’s a mid-forties African American entrepreneur in Detroit, and he has a conference, and he reached out to me three years ago and asked if I’d come speak. Marina, my assistant, said I should look at this. It was a thought leadership conference where I think 80 percent of the attendees and speakers were African Americans. And I was like, I’ve never been invited to something like this.

Spending time with Hajj has been eye-opening in many ways. While I was driving through Detroit with him, he pointed out to me one building that was owned by an African American family. This was after he said to me that over 85 percent of Detroit is African American. One little thing I remember from then as well: We had to drive like 15 minutes to another ATM that was kind of safer. Hajj explained the whole situation to me, that there were some streets or areas where you couldn’t just take cash out and assume you wouldn’t get mugged. Which I never would have thought of. You just take it for granted that if there’s access to water, there’s access to cash.

This reminded me of my childhood: I grew up in Seattle, in what’s now called the international district, but it was called Chinatown then. It wasn’t a good place to be, even though it was a good place to be. When you’re a child it doesn’t feel dangerous. But my parents were always worried; they thought everything was dangerous. They knew stuff that I didn’t.

What do you actually do, then, with all these observations, all this new awareness that everyone is having very different, nuanced experiences?

This will sound weird, but I had this epiphany recently that I’m an Asian American person. Which was like, “Oh, I’m not a white American person.” I had detached myself from my identity and how I look, and then I realized that maybe, by being an Asian American, I can go everywhere. I’m like a Type 0 minority – I can go many places, and people will say, “Are you one of us, or are you not?” I’m trying to use that to connect dots that are disconnected.

We did this big project with a school district in Paintsville, Kentucky, which is in coal country. So many people were like, “Have you read J.D. Vance’s Hillbilly Elegy?” And then people were like, “Have you been there?” And I was like, “No.” Being there made me check my biases. I visited on a tech jobs tour initiative, and I didn’t realize it at the time, but Paintsville is famous for being visited by LBJ in the ’60s, as representing one of the poorest parts of the United States. Automattic is totally based around remote work, so we set up this program where students can be remote and learn about jobs in graphic design. We also set up video calls so they could interview designers about their work, and they talked to people like Hajj.

I’ve connected David [Gibson, the superintendent of the Paintsville school district] and Hajj together by text-messaging, and it’s like they are two worlds apart – Detroit and Appalachia – yet both of them are dealing with similar levels of inequality. They’re both using technology, but not Silicon Valley tech geek stuff. It’s practical technology, like videoconferencing and other “blue collar tech,” as I like to call it, to expand their zone of opportunities. The people reshaping how the tech landscape will work, it’s not just people in their twenties and thirties, and it’s not just Silicon Valley.

Which is to say, thinking about diversity in design doesn’t just have to do with race and socioeconomics, but with age and just plain digital literacy.

It is. Something about falling so hard, and lying on the sidewalk in the darkness bleeding alone – it gave me focus. The process of recovery kept teaching me new things, partly because the experience let me see what my body might feel like fifteen years from now, if not sooner. With the luck of my health turning out fine, it got me to think more carefully about what I do with my remaining time on earth. So inclusion became my passion.

John Maeda photographed at the 2018 Adobe 99U Conference by Ryan Muir.

This article first appeared in 99U's "Hurts So Good"-themed magazine issue. Watch Maeda's 99U Conference interview here.