Tell me a bit about where you come from.

I moved to the Bay Area from New York City in January 2015. I grew up in Bethesda, Maryland, a suburb of Washington, DC. My parents moved to DC in the early 1970s for work. I don’t think they ever thought that they would stay there as long as they did but they both began their careers in DC. My dad’s originally from Brooklyn and my mother is from Germany. They now spend half their time in New York and half in DC.

New York is really home for me. That’s where most of my friends and family are. I moved there for college in 1997 and pretty much stayed through the end of 2014.

Tell me a little bit about your legal background.

I went to (City University of New York) CUNY School of Law, which is one of the rare, public interest law programs that exists in the country. The curriculum focuses on “client-centered lawyering,” and Queens, where the law school is located, is said to be the most ethnically diverse urban area in the world. As a student I worked on public benefits, housing, immigration, and domestic violence related cases. It was a great place to work on cases because the clients were so diverse and they brought with them so many different ideas about how they wanted to resolve their issues.

My career after law school spanned legal and non-traditionally legal work but all in the social justice / nonprofit sector. In 2010, I began working with a criminal defense firm that handled mostly federal cases. I primarily worked on what are known as “CJA” or “Criminal Justice Act” cases, which are indigent defense cases assigned to private attorneys by the federal courts.

There’s a lot of dysfunction in our criminal justice system and being surrounded by problems can be exciting. The difficult part though is that often your hands are tied, and that’s the real struggle. You see tragedy on a daily basis, and for most things, you can’t do much to make things better. For me, the victories were typically small ones—shaving off a few years of someone’s sentence, securing a decent plea agreement from an aggressive prosecutor, visiting a client in jail when the vending machine is actually working so that you can buy him some junk food. Small victories. I think this is particularly true for federal criminal defense work, which is mostly what I did.

Walk me through your transition towards tech.

I started with creative projects that presented experiences of criminal justice in the U.S., and I turned to digital technology as a tool. I launched my first project, a questions and answer project called Ask a Prisoner, at the New Museum’s Ideas City StreetFest in 2013. It was a collaborative effort with a friend, Sheila Rule, and the Civic Duty Initiative, which is a group of incarcerated men committed to giving back to the communities that they once harmed. The project lives on a Tumblr site. It was super simple.

A few months later, I ran into an old friend, Luke DuBois, who had just recently been appointed the director of a digital media program housed within NYU Engineering School. We started talking about things, I told him a little bit about what I was working on and thinking about. He successfully sold me on enrolling in his program.

Going back to graduate school changed a lot for me. Initially, I wanted to make art and tell stories. But most of the courses I took were about digital product development and user experience design. And then, I naturally gravitated towards product development in the areas that I already thought a lot about—the law, the criminal justice system, government. A professor of mine, Beth Noveck, introduced me to the civic technology world—building digital tools to help government provide better services. For a course of hers that I took during my first semester, I developed a simple data project through which I transformed clunky data from the New York State Parole Board’s website into a more usable format for researchers. At the time, I was representing a man in front of the parole board so the course gave me an opportunity to think about my legal practice from a new angle.

For 2015, I worked as a fellow with Code for America, which gave me an opportunity to build a digital civic engagement tool in collaboration with two other teammates. I recently accepted a position with 18F, a consultancy that helps federal agencies develop better ways of delivering digital services.

What is it like working in Civic Tech and Silicon Valley?

The civic tech world is pretty wonderful, I find. I really feel like I stumbled into a community of smart, thoughtful, hard working, creative people with diverse talents. I’m working on similar issues to those that I handled as a lawyer, since usually my legal work involved managing interactions between individuals and government agencies (whether that individual was trying to secure public benefits or challenge a criminal charge). My work now focuses on systemic change rather than client advocacy, but the end goal is similar: to make government better serve the public interest. Right now is a particularly exciting time to work on digitizing government services because it’s relatively new. The agency that I’m working with, 18F, hasn’t even been around for 2 years. I feel like we’re all figuring out a new path together, which is exciting.

As far as Silicon Valley, I don’t go there that often since I work mostly in San Francisco. Even the metaphorical Silicon Valley.

I guess I’ll mention the emphasis on change, impact, and scalability. Lots of people want to make things really big around here. But I’m used to representing individuals. So in the past, keeping a client from serving a prison sentence would be an example of success. And hearing updates from them over the years about how they’re doing alright would bring me happiness. In other words, the personal relationships were what made the work meaningful for me.

I hear more of this ‘big’ talk when I’m  out and about, at conferences, or at social events. I hear public interest work talked about as “change making.”  I often hear people say things like, “I really want to make ‘impact’” even though they’ve likely never even volunteered an hour at a soup kitchen. I hear people talk about how big they want to make something before being clear about what the actually want to do, and why they want to do that thing. Scalability and impact make sense when you’re selling something, and I think this is one reason why people talk about this so much out here—most people in tech are in the business of creating products for market. But when you’re caring for people, these terms can come off as dehumanizing and impatient. For me, it kind of shoves the heart of public interest work out of the conversation.

I’d love to hear anymore differences that you’ve noticed switching industries, switching cultures. What else has been noticeably different for you?

A lawyer friend once said to me, “there’s no beta appellate brief.” I think that really sums working in law versus working in early stage product design. In law, you don’t really get to get feedback and do it over in the same way.  You polish up your work and you put it out there and that’s it. And there’s a lot at stake.  The law is iterative if you look at how our laws adjust over time, but practicing law isn’t that way.

In your point of view, for the question of what struggles have you faced during your time in tech, you just put the two words “fitting in.” I’m curious to hear you elaborate.

Yeah, in ways, I feel like a bit of an oddball. I’m a lawyer by training though these days I work mostly with designers and developers. I often find myself thinking about risk mitigation when colleagues are thinking about creating cool, cutting-edge features. I think we learn a lot from each other, but I notice how much my background influences the way I think about my current work on product teams.

Something I am focused on is how one’s life experience perfectly informs us for the roles we play in this tech world. You could have spent 15 years doing something in tech, but that would not have equipped you mentally or emotionally for what you’re doing now. But it’s common for people to not value a breadth of experience versus laser-sharp specialization. It’s ironic.

True! Perhaps because it’s harder to measure and to understand? But I also feel like here there is a certain softness and acceptance towards people who’ve taken different paths and changed. I think in New York it’s it’s much more like, “how many years did you stay there? Where did you go to school? What is your linear trajectory?”  And here if you say, “I did this, and then it didn’t feel right, so then I did that.”  People are like, “Cool, tell me more about that.”

I think about the differences between New York and San Francisco. In New York, there are so many more equalizers. In food, there’s the dollar slice, the bagel, everybody eats those. Everybody engages in some of the same core things in that city, and it preserves culture in a way that it doesn’t, here. 

The subway functions as an equalizer as well. It’s cheap, it runs all night, it goes almost everywhere, and most people use it—regardless of income, age, nationality, etc.

There’s a lot more mixing in New York than there is in the Bay Area. It’s a much larger city than San Francisco so there’s more opportunity to have interaction with people who are different from you.  And living is rougher there so everyone is familiar with putting up with discomfort, having less space, less quiet, and making the best out of what there is in the moment. Exploration is a big part of enjoying New York—discovering something new or opening up to a new kind of conversation. So when tech companies offer in house food, in house health care, transportation—they’re consequently isolating their staff from these things. It’s good to have all of these perks but it’s also not good.

What do you see yourself doing in the future?

I definitely feel like I’ve found a cohort in the civic tech community. Then, having practiced law, I care a lot about applying my new skills to help to under resourced advocates including legal aid attorneys. I also think about teaching and writing.

What advice would you have for someone working in tech who wants to use their skills for the greater good?

There are many local nonprofits with thin resources that are doing really important work like protecting digital rights, increasing digital literacy, and just more generally using technology to serve the public interest rather than to create commercial products. And then there are many Bay Area organizations that are not tech-oriented but care for the many marginalized individuals throughout the Bay area. Idealist.org is a good place to look and see what interests you.

Give yourself space to try to learn about a new problem without feeling pressure to build anything. If the only thing you are able to accomplish is that you start to understand and relate to someone else’s struggle, you’ve done something hugely important. If you are up for talking about what you learned with others, maybe writing about it, that’s another helpful that you can do. Just because you’re an engineer or a designer or whatever you normally do, doesn’t mean that that’s all you have to offer.

Be ok with small victories. It takes time, resources, and support to build tools that will actually be useful. Social problems are typically complex and involve lots of stakeholders. It’s hard. I’m a big advocate of supporting existing projects rather than trying to start something of your own from the start.

Support efforts to make your workplaces more inclusive environments.

If you are interested in helping improve government service delivery, check out 18F and USDS as they’re always looking to grow their teams. Code for America focuses on improving service delivery at the city and county levels and they have local volunteer groups called brigades that lead weekly hacknights.

If none of this stuff interests you, giving money to local community based organizations works too.