Hello! Who are you? Tell us about yourself. What are you passionate about? What do you enjoy doing?

Ahh! Hello! My name is Dezzie. I like to eat, think, and take things apart. 

How did you get started in product design?

Oh dear. There are a few stories. This is going to be long but it was complicated:

During high school, I started making websites. I was obsessed with modifying how my OS looked, I used to hack my Windows install so it would look like Mac OS, things like that. My very first website was on Geocities and it was a collection of things you could do to make your OS look like the dashboards in Starcraft. As I craved more control and freedom over what I could make, I would move my site to more “real” places, where I could use code, like Tripod, or Angelfire.

At the same time, unrelated, I was covering for a classmate who never did his homework because he went to too many raves (I was obsessed with electronic music, too, but didn’t get to go to shows). If I covered for him that week, he’d bring me a mix from that weekend. One time, he didn’t bring anything, and felt bad, so he offered me a burned copy of Adobe Photoshop 6. I asked him what that was, and he said, “It’s like MS Paint, but way better.” I took it home and it changed my life. Eventually I outgrew what I could do on the free hosts, and I started trying out for blog rings–which was a thing where, a person who owned a hosting account would give you a subdomain if they liked your stuff, and you just had to come up with a new layout for your website every week or so.

That was all a hobby, but it was all-consuming. If I wasn’t doing homework or at school, I was doing this. Once I was in college, this let me work for the university web group as a front-end developer, which, as far as work-study jobs go, it paid twice as much than other jobs on campus. Plus, I learned a ton from the people on the team. When the A List Apart article on responsive design came out, we started doing it immediately. When 37Signals came out with Ruby on Rails, the team made a timesheet app the next week. I got to work with a dedicated content strategist and an information architect. My code was clean and standards-compliant. Looking back at that situation, I had no idea how lucky I was and how much I would learn. It was such a blessing for the future. I loved what I did. I started skipping class. I did this in high school but in college it was not sustainable. A combination of working on websites for everyone, and also not being interested in my premed major landed me on academic probation, and then depression.

I got a strong message from professors and guidance counselors that this work was a bad idea, the the hobby was more like a vice. There was no “web design” major. People still remembered the dotcom crash. No one suggested computer science or graphic design because no one saw the connection between the two, and neither department took the web seriously. Plus, you don’t go to a fancy school, if your family is working-class and no one’s ever even graduated high school, to play on the computer. So at this point, for both practical and emotional reasons, I pushed it all away. I needed to get serious about graduating and landing a job after graduation. It turned out well in the short-term. I got deep into the psychology research scene at the university and started a PhD after graduation, intent on becoming a professor in academia. The irony in that turn of events is hilarious now, given the changes that academia and the tech industry have undergone since.

Once I was in grad school I sort of tried to bring back design and tech in my doctoral work, but it got major push-back, and pretty soon I was miserable again and ended up taking a leave of absence. Since I didn’t have my funding during that time, I started freelancing to pay the bills. I got a job as a Mac Genius too (which has its own story). I still fully intended to finish my PhD, I just wanted a break. But the Genius job, as much as it could suck, was one of the best decisions of my career, because it was watching users fail at using software day in and day out. It made me understand how things could be beautifully designed–but not always usable. And so the love affair with design started again. For the first time I realized that this was what I wanted to be doing, and I didn’t care about being successful in other people’s eyes. I kept failing at those careers anyway, and had to find a way to make a living.  By now both the tech industry and academia had changed enough that no one was denying that web stuff was just a hobby. Few people in academia were finding stable work as a professor.

When my leave of absence was up, and I went back to my program, I barely finished a semester of class. I remember going into my advisor’s office, where I just told him I was quitting and joining the tech industry. It was weird and freeing and awesome.

After that I worked for an immigration non-profit for about a year while I put together my portfolio and brought my skills back up to speed. Eventually I felt ready to start networking, and seeing if I could get my portfolio out there, since the DC tech scene was in a boom. I got lucky on my first try, probably because the president of that agency was incredibly wasted. They were hiring for a government contract, and sure, he’d interview me. I was not allowed to know who the agency was, or what I would be doing, which made me uneasy. I was planning to just go and do it for practice. The Space Shuttle was supposed to be doing a flyover of DC that day, and I really thought about skipping the interview to see it–luckily, I chose not to be a dumbass that day.

Audrey Chen was building a design and tech team at a brand new government agency called The Consumer Financial Protection Bureau–the brainchild of Elizabeth Warren, who recently announced her presidential bid. We had a conversation in that interview, where she asked me why I had never pursued design until now, and I told her it was because I couldn’t see myself truly helping people through it the way I could in other jobs. So she told me her own story, about how after she was a newly minted designer with an art and math background, she got a great job–but was assigned the Phillip Morris account on her first day. She never went back to that job. After years of doing very neutral work, she took the CFPB position because it was the first time she felt she would be able to help people. That really resonated with me, and it’s why I took the job.

The setup at the CFPB was great, they had a fellowship where they hired senior-level people from around the country with amazing experiences to work remotely with us. On top of that, we were a government agency, so we had different motivators and indicators for success. It was a great environment to learn how to champion users. The foundation of how you work as a designer is shaped by your early experiences and habits, and having these folks and design problems to work with was again–super lucky.

After a few years there, I realized I just didn’t really see myself in government–even though I was fully invested in the mission of the agency and I was inspired by the work we were doing. I was just getting an itch to do something different and I didn’t like how everything found its way back to an election. I was also mad that I was making about 30K less than a government worker for the same exact work, could not be promoted or lead projects, and couldn’t go to conferences.

So I went and worked for an agency. They had a great UX team. I learned a lot from my manager there and got promoted really fast. But the drinking culture was too much–one time me and another female colleague were asked to go to a meetup where our president introduced us to his friends as, “The women I told you I’d bring you.” I think that experience just pissed me off and I went through a phase where I wondered where my place in the industry was. So I did what all frustrated cerebral people do–I applied to grad school. I got to the last, final interview phase of a famous product design program, then gave the worst interview of my life, and got rejected. That year was a lot of validation and rejection at the same time.

I had to think about what I was looking for–and it went back to trying to connect the dots in my background. This was around the time where companies were investing heavily in building in-house design orgs–and IBM was one of the industry leaders in the movement. Their artificial intelligence division seemed neat–and they were hiring. I crashed SXSW that year, literally loitering around, got into IBM Design’s party-and immediately decided I needed to work there. Apparently they felt similarly, because about a month later I was looking at a move from DC to Austin to start on their Watson design team.

I keep saying how I learn a ton in every job, but hands down, the experience I got working at IBM, is where I found product design and product design found me. It was the most formative job I have ever had. They are known for their design thinking work, but what they don’t always mention is that they have a lot of classically-trained designers behind it, and there is a lot you can learn from them. I worked for a lot of ex-industrial designers, who put our design research habits in the tech industry to shame. Many of these people worked there to fund their art practice. Learning from all of those perspectives transformed how I worked on the “computational” side of things. It was when I stopped thinking of my work as, “the thing that I seem to do very well and can pay the bills” to “this is my vocation.”

After a few years there though, the whole conversation around AI started to go places where–knowing I wasn’t working on anything evil was nice, but I wasn’t really working on anything good either. I felt confident in what I could do as a designer and I realized it was time to start choosing my work more intentionally—to align it more with my values. Without getting too much into it, I’ve always been passionate about the open web. I feel very strongly about the walled gardens we’ve built. I am not the type of person that can have a day job working on whatever so long as it funds the side project I really care about. Too many potential points of failure in that approach to life. So I applied to Automattic, which I had followed since WordPress 1.0, and seemed to be one of the few companies who actually were making the web a better place. Now I am here, hello.

To summarize, this is probably a story that you don’t want to use to inspire people to get into product design. I got into product design because:

  • I got pirated software from a kid who was probably a drug dealer
  • I thought I wanted to be a doctor, but it was just my parents’ idea
  • I was on academic probation at Notre Dame
  • I couldn’t make it in academia
  • I got into a fight with a Mac Genius (I won, by the way)
  • I was broke and I don’t have parents who would just fund me like other Millennials do
  • I am good at this and it was about damn time

Where do you work today? What is your title?

I am a Senior Product Designer for Automattic, Inc. Automattic has been one of the companies I’ve admired in the industry for many years. I’ll point out that Matt Mullenweg either rejected or forgot about my application back in 2014. But four years later it worked out, probably for the better. 

How big is your company? How big is your design team?

800-ish, with 60-ish of those in the design organization. 

What types of things are you responsible for day-to-day?

Everything. Right now I am responsible for all design research and execution related to my projects. The hardest parts are communication, alignment, scoping, and planning, because we are all-distributed. The easiest parts are focusing–because I don’t have to deal with a silly open office plan anymore.

What do you love most about your work?

I feel very lucky to work on something that helps run a large portion of the internet, but supports an open web. It would be nice to contribute in bringing down some walled gardens someday.

What drains you at work?

The tax of working in an all-distributed company. The tax pays for good things, but it is still a tax on the work, like not being able to have in-depth discussion or good critique sessions with everyone present and engaged. I was spoiled in this area earlier in my career. I have not found an equivalent alternative to sketching something out with a colleague. If I feel like I can’t dig into a design problem with my team, even if it’s through no fault of their own, it’s very draining.

Can you walk us through your typical work day?

6:00amCatch up on A List Apart editorial team stuff I do as a side project.
Prepare daughter for her day. Cook breakfast. Family stuff.
8:00amWalk to neighborhood coffee shop and do deep-focus work (I work well from coffeeshops and do my best work in the morning). I will start the day in my home office if I need a large monitor though.
12:00pmNeighborhood gym for a 45-minute bootcamp. 
1:00pmConsume protein, plants, and fat. Stand in sun to absorb vitamin D. I hate lunch, it makes me sleepy and destroys my focus. I try to schedule all my meetings after lunch.
1:30pmSecond part of my day is in my home office. Meetings, teammate conversations, work that I don’t need to be as focused with.
4:00pmCease working, go downstairs, collect toddler, take her on a walk. From here to the end of the day I’m busy with running a household and spending time with my family. If I have to, I will work more, but I like my boundaries.
8:00pmStar Trek, right now it is Deep Space Nine. I don’t really watch other TV.
10:30pmFall asleep reading a book made of paper

Where do you turn for inspiration?

I actually don’t seek out inspiration. I’m a believer in the line, “Inspiration is for amateurs–the rest of us just show up to work.” It’s something that I have leftover from not having the luxury of starting my design career in a coddled way. A better line is, “Inspiration comes of working,” which I got off a folder made by the Japanese brand Delfonics–but which sounds very Mexican too.

I do intentionally think about what motivates me, what stimulates me, so I can I keep my creative energy healthy. For example, I need a consistent drip of intellectual stimulation–so I turn to books or critical articles on the web, or good conversations. They’re usually not about design either–the design (and tech) industry doesn’t do a good job at connecting its work to the broader world.

Usually if I have writer’s or designer’s block it’s also not so much a question of whether I have been sufficiently inspired, but because there is lack of alignment and clarity about the work. If it isn’t, it’s probably fatigue, which I’ll exacerbate by forcing myself to chase an invisible spark. At that point, the best thing I can do to keep my mind clear and creative is by shutting it off. I do that via exercise, sleep, manual labor, meditation, or playing with my child.

That’s a long-winded way of politely saying that I think most design inspiration sites, blogs, and communities are not good. Those are good for consuming, not thinking. They focus on popularity and trendiness, you’ll end up with all FOMO and little work to show for it.

What design or project are you most proud of? (It can be recent or older).

This project is not publicly available anymore because it got taken down by IBM PR’s team. That in itself is part of why I’m proud of it. It was a skunkworks a few friends and I did in early 2016. Each of us needed a way to blow off some creative steam. In my case, I had been wrestling with this question about the effect of people’s personality on their thinking and behavior patterns. I had been observing much on how social media and the modern web held our time, and I was worried that the next presidential election in the US would be influenced by all that.

At the time, one of the few profitable uses of machine learning technology was for scaling up marketing campaigns. Having friends in government who had run presidential campaigns, and hearing them talk about how they approached the work, it seemed incredibly similar. There were a lot of what-ifs between psych and design and tech that I sort of didn’t want to know the real answer to, because I was afraid I wouldn’t like it–Facebook, for example, had caused a stir in the scientific community a few years before when it was revealed that they had been manipulating people at risk for depression without their consent and without providing a means to undo any damage.

So my friends and I created a little thing that would go through a person’s Twitter feed, and make a prediction of who they would vote for based on their personality, attitudes, and behaviors. The amount of content people produce on their social media profiles is more than enough to generate a full personality profile. This is in addition to the explicit content individual posts convey. At the time, there were tons of people in the running, and we hadn’t reached the primaries yet, so it made the project something that people could use to explore candidates that they hadn’t considered.

For me it was a lot of fun creating the personality profiles of all of those candidates. I used their social media feeds but also transcripts from debates and interviews, leaked emails, speeches, and content from years before they ever ran for president. But when we shipped the thing and started testing it, we saw that a ton of people aligned most with Donald Trump. If you followed the news at that time, no one took him seriously, especially in the time leading up to the primaries. The thing got shut down on the basis that it was obviously not working and would cause a PR backlash.

I remember how disappointed we were, and I personally felt like I had dragged my friends on this crazy idea. It kind of reminded me of the times I tried to connect my design and technology interests when I was a doctoral student, and no one would buy it. So I felt like I was both a bad “idea person” and a bad leader. Then of course, the election happened and we started finding out everything that was done on social media. This was a little vindicating, but it also meant that some of my biggest fears about what people would end up using the internet for were coming true.

What career advice do you have for product designers just getting started?

I don’t think our work is ethically neutral anymore, as mundane as the project you think you’re working on is. Everything’s always been in flux. As the work we do now has broader impact over our lives, our minds, and our world, it’s important to know the context of how some things came to be. Some aspiring product designers almost worship the four big tech companies or startup culture. But do they actually know what the business models or histories of those products are? Are you going to be comfortable, as a designer, in being party to some of those things? If you want to be a product designer, you have to think about those broader things. If you don’t think you have to, you probably won’t be successful as a product designer, or you’ll need to be okay with having those skeletons (and their effects on all of your users) in your closet.

This is one of the reasons that I dislike most design inspiration sites, and the whole cult of celebrity that’s spawned around design teams and individual designers. Those sites rarely tell the story of the work, who really was involved, and how much of it is real.

I also urge people to get acquainted with internet history, and the careers of industry veterans. While the tech industry undeniably bankrolls much of the design work you see today, the design industry itself wasn’t always so welcoming to the tech industry, particularly when it came to the designer who taught themselves. The design industry didn’t take the web seriously for a long time. The people that paid it forward for us to enjoy the opportunities we have today, are more often from the early web community, not the classically-trained design community, or even the tech industry for that matter. Yet there’s this stigma towards people who used to work under titles such as Webmaster, or web designer.

Lastly, I try to tell people not to model themselves or their idea of success against what they see on social media. A designer who has thousands of followers or who did something that went viral does not mean they’re a good designer. You’ll figure stuff out about some people as you progress in your career, and hear stuff through your networks and trusted communities. Work on your reputation and portfolio over your personal brand. You might feel like a little fish in a big pond but it’s actually a very small world.

Where’s the best place for folks to learn more about you or follow you?

I tweet sparingly @thedezzie, and have dusted off my blog at dezz.ie