Photo by Katie Thompson
Over the last fifteen years, Chris Messina has enjoyed an unparalleled vantage point in tech. Chris was the Developer Experience Lead at Uber from 2016 to 2017 and worked with Google as an 'open web advocate' and UX designer from 2010 to 2013. Yet what sets Chris apart isn't those experiences at the giants of Silicon Valley, but the multitude of other projects and concepts he’s kick-started along the way.
In 2007, Chris invented the hashtag, proposing it as a solution for vertical/associational grouping of messages, trends, and events on Twitter. He's also known for his involvement in helping to create the BarCamp, Spread Firefox and coworking movements. Chris is now using his hindsight and curiosity to look forward to the next fifteen years in tech — and prevent it from becoming an enemy to our human nature and relationships.
In advance of his first appearance on the Turing Fest stage this August — and the workshop on becoming a more emotionally fit entrepreneur he'll be leading with psychologist Dr Emily Anhalt — we caught up with Chris to learn more about his journey so far, and what he's learned about building a fulfilling career in the frenetic tech business.
We called Chris at his brother's farm in New Hampshire — with a background chorus of sheep. Back in March, Chris decided to leave "the Willy Wonka bubble of Silicon Valley" to spend the next six months speaking, consulting, visiting friends, and exploring new corners of the world. It's another turn on a path that's intriguing in its unpredictability and diversity — and its impact.
"It's a funny juxtaposition," says Chris, "being interesting and having impact. Those two things don’t always go together." Yet in his career, he's made it work. Here are the philosophies that have guided Chris's career, projects, and focus in the rapidly-changing worlds of design and user experience...
“There are some first principles that differentiate my approach and the kind of success I’ve found,” shares Chris. These include never pursuing the obvious kind of success that people tell you to pursue.
Money was never really a thing that really interested me all that much. I was a lot more interested in a couple of things… one was changing culture and spreading the benefits of social technology to as many people as possible. Another was looking at ways of creating what are considered to be more generative structures.
When Chris first got on the internet and saw the scope for creating projects with it, he understood the potential of being able to participate without needing permission from anyone else. Through his work, he wanted to create more opportunities like that.
"I don’t necessarily think about conventional roles or titles as being all that meaningful. I suppose this is why I haven’t spent that much time at big companies, per se," he explains. "I spent maybe a total of four and a half years working at corporate companies. Going to those companies was a bit of a stretch for me, because I know how curious about the world I am and how uninterested I often am in just building a single product or building within a single team."
For Chris, it’s always been about the big picture potential of tech, not just a single product or a certain role on a career ladder.
Whether it was the early BarCamp events that he helped to organise, or launching the first coworking spaces, Chris found himself thinking, "How do I make something that’s bigger... something that allows others to participate with as little permission required from me or a central authority as possible?"
"There is a way to make money or a living doing that work, but that aspect was always secondary for me," he tells us. Rather than creating a franchise model where he would own the concept and selectively grant permission from others to implement the idea, he is more interested in applying open source philosophies to his work. "You can essentially create a blueprint that people can find on the internet, adapt that idea to their own context, and create a community around it," says Chris.
Giving your work away isn't for everyone, though. "It depends on your goals... and there's a difference between free as in beer and free as in freedom," says Chris. "In the UX and design space in particular, it’s particularly challenging as you don’t want to be doing your work on spec – giving away your work for free and then devaluing your work and everybody else’s."
If instead what you’re trying to do is set a standard, you can create a bigger pie for everyone to participate in. You're creating a space in which everyone is experimenting and sharing the results of those experiments to get to a better, bigger outcome.
This could be as simple as creating a platform, framework or set of standard widgets and components that others can build and expand upon, like WordPress or Bootstrap. Designers can then focus more on style over complex interactive elements, and lower the barrier to entry for new users.
Deciding whether to give away work for free goes back to your goals and your personal business model. Chris adds: "If you’re making a living doing design work, obviously you can’t do it all for free – but a lot of these basic things are about agreeing on a baseline. The way I think about it… I’m not really a big sports fan, but compare being a football player to a team owner to the [National Football League] itself: it’s the league that creates and maintains a set of standard rules so that many more people can compete around the same activities and goals."
I’m more interested in creating things more like the NFL, where lots of people can participate and there might be multiple teams or companies competing in the same space, rather than just trying to be an individual football player. When I think about things like the coworking movement or hashtags, those were designed to make it easier for lots of people to take up those core concepts and then to create different contextual applications that could solve problems for people.
In a Medium post titled, "The full-stack employee," Chris wrote that “innovation is found at the boundaries between disciplines”. This neatly applies to his own career too. "In many ways, some of my success came out of being trained as a designer, but working in more conventionally engineer- or developer-centric contexts where there just weren’t many designers," says Chris.
"Bringing together my skills in visual and communication design helped me help developers to tell their story better. Previously they thought their apps would sell themselves. But really they needed help to spread the word and raise awareness to what they were building. And helping them is a very basic example of how I brought design and software development together."
"Probably the other thing that’s impacted me the most, but has also been one of the biggest burdens, is my curiosity," says Chris. In the last couple of years, his interest has been in human-to-human relationships and the structure and psychology of those relationships.
"A lot of what I’ve learned about human relationships are informing how I think about conversational computing and the way in which we construct relationships with bots like Alexa or the Google Assistant," he explains. "What type of relationship do we want with it? What language should we be able to use to describe our needs to these things? And how should we expect those things to respond when we ask them about themselves? Like, 'Alexa, where did you come from?' 'Who is your father?'”
"As a designer, you have to be prepared to think about the various subtle nuances that need to be built into conversational agents to make them feel less creepy by eliciting the kind of information they need from users to serve their needs."
Chris explains that there were several benefits from spending time at big corporations like Google. "First it was humbling… all of a sudden I was amongst some of the most brilliant and intelligent people," says Chris. "The range and types and styles of intelligence gave me such a broader sense of the different capacities that people have. Not everyone’s the same, and the degree to which people interpret or experience the world is so rich and varied."
"When you work for a big company as opposed to a small company – where you might have a lot more autonomy or agency or ability to get things done – that can force you to slow down and work with people and meet them at their level."
Working at Google and Uber helped Chris to become more aware of his own biases and ways of thinking, he shares:
I try to recognise that everything I think comes from all of the experiences I’ve had in my life. This is true for everyone else as well. So when you’re having a conversation with someone and you’re not connecting or making sense, it’s important to dig deeper and ask, ‘What brought you to this conclusion?’ or ‘What’s informing you right now that happened in your life and is so clear to you that you’re fighting for this position, because clearly I don’t have the same experience and I want to understand'. It’s not that either of us is wrong, but we have a different kind of algebra of sense-making. Figuring out how to negotiate that space with mutuality is critical.
"When I went to Google I was actually quite resistant," shares Chris. "I thought, I’m going to this big company but I don’t want to sell out, I don’t want to become just a stooge for Google, I want to have my own identity still."
One of the reasons I went to Google was because I felt very strongly and passionately that the social web needed more competition, and I was very afraid that Facebook was going to become the sole identity provider and essentially be your gateway to the internet… that everyone would have a Facebook account to log in to all the different websites and ruin the NFL, so to speak. I thought Google was the only company that could mount a competitive contest and do it in a way that would ideally enrich the web as a platform, instead of trying to own it all for itself.
"Whether that was the right or wrong assumption, I went in there thinking I would be able to maintain my independence," says Chris. Looking back, he admits he did it in a way that was probably more prickly than necessary. But overall, he looks at his time at Google as a valuable learning experience.
"I’ve learned how to centre myself and my capabilities within what I know, what I can do, and how I think about things," says Chris. "I know that my specific uniqueness and the way I see things comprise the value I bring to anything that I work on. But it's taken me a long time to get there."
One of Chris's most impactful projects was working on designing the profile for Google+ and unifying 46 different teams’ approach to representing you for the same Google account. "Although there’s some value in these distinct representations, it also makes it very difficult for an individual to maintain their privacy with so many different choices," explains Chris. He also worked on creating the Google Developers brand, bringing together previously-disconnected teams in developer relationships, developer marketing, and other teams publishing documentation and with APIs for their products.
Chris adds: "Going through a big corporate brainwashing programme and having survived with my soul intact gives me confidence in myself and my own abilities to transcend those environments..."
When asked about his habits and if he blocks off time for focus versus consuming information, Chris laughs. "Unfortunately I don’t think I have really have great habits yet… I’m constantly grazing."
I consume an enormous amount of information, probably a little bit too much... but there’s so much to keep up with, so much going on, and so much to try and make sense of.
One of Chris's favourite sources of reading and listening content is Techmeme. In their podcast Techmeme Ride Home, they discuss the site's top stories and summarise the day’s news in tech. Chris explains, "It's a distillation of a distillation… the site is a cup of coffee and the podcast is an espresso shot. There’s so much information that comes through it and the way in which they group and review it is really effective to get a sense of what the most important stories of the day are."
Looking at his Twitter feed, Chris adds: "Kara Swisher is a great person to follow. She and Scott Galloway run the Pivot podcast, and I find their takes really interesting. I don’t always agree with everything they say, but from a more liberal-leaning side, they do a pretty good job of bringing that perspective to tech."
Chris is also known as being a very active user on Product Hunt. "It allows me to surf the future," he says. "I can see what young and new developers and designers are building and what problems they think people have.”
"The ability to see what people are thinking about and how their products attempt to solve specific problems helps me sample the leading thinking on emerging trends," he adds.
"When I do talks [like Turing Fest] it’s a moment where I can distill what I’ve been thinking. There’s also a lot of urgency, since I’m an amazing procrastinator and I always think there’s more information that I need to gather before I can say something intelligent," says Chris.
For Chris, preparing for a talk marks a point at the end of a sequence of thinking, a sequence of experiences, or a sequence of things he has been exposed to. "I can bring it all together and think, 'How is this story changing for me?' Or, 'What’s new since I last gave this talk?'”
"I wouldn’t say I’ve got it nailed down yet. I need much better discipline. With my travel, it's harder to get into a rhythm. But I think it’s about constantly grazing information, putting things out on Twitter, seeing how people respond to them, noticing what people find interesting or provocative, and following my curiosity. It got me this far, after all!"
Stay tuned for part 2 of our interview with Chris, with his take on how tech companies are failing society, and how they can become better corporate citizens...