Convergence, Ep4: Jess Fjeld – Overcoming Life Challenges & AI Ethics

Episode 4 of “Convergence” features a conversation with Jess Fjeld, the Assistant Director of Harvard’s Cyberlaw Clinic and an expert on artificial intelligence governance. Jess describes the increasing relevance of AI in our lives, offers principles for thinking about AI governance as dispute systems increasingly use this technology, and reflects on the importance of self-compassion.

“Convergence” is a bi-weekly, limited series of conversations with thought-leaders and practitioners at the intersection of dispute resolution and technology. Host Oladeji Tiamiyu will focus on such topics as the role technology has had in resolving disputes during the pandemic, various ways  technological tools have historically been incorporated into dispute resolution, and creative use cases that technology presents for resolving disputes into the future.


Oladeji Tiamiyu


Jessica Fjeld is a Lecturer on Law and the Assistant Director of the Cyberlaw Clinic at the Berkman Klein Center for Internet & Society at Harvard Law School. She focuses her legal practice on issues impacting digital media and art including intellectual property; freedom of expression, privacy, and related human rights issues; contract; and corporate law. Recently, she has emphasized work with AI-generated art, the overlap of existing rights and ethics frameworks on emerging technologies, and legal issues confronted by digital archives. She is a member of the board of the Global Network Initiative, a multi-stakeholder organization the protects and advances user freedom of expression and privacy around the world.

Before joining the Cyberlaw Clinic, Jessica worked in Business & Legal Affairs for WGBH Educational Foundation, where she advised the American Archive of Public Broadcasting along with numerous WGBH productions. She began her legal career as an associate at Skadden, Arps, Slate, Meagher & Flom LLP focused in corporate transactions. Jessica is also a poet, the author of Redwork (BOAAT Press, 2018), and the recipient of awards from the Poetry Society of America and the 92nd Street Y/Boston Review Discovery Prize. She holds a JD from Columbia Law School, where she was a Hamilton Fellow, James Kent Scholar and Managing Editor of the Journal of Law and the Arts; an MFA in Poetry from the University of Massachusetts; and a BA from Columbia University.


Cyberlaw Clinic at the Berkman Klein Center for Internet & Society

Principled Artificial Intelligence



Oladeji  00:01

1234 Welcome to convergence with Oladeji Tiamiyu. You. So first, I want to thank all of you listening in supporting “Convergence.” Honestly, the show has gotten way more attention than what I could have expected. Many of you have reached out to me via my LinkedIn account, or on my email [email protected]. My aspiration has been to provide space for conversations related to technology, and dispute resolution. Yet regardless of our level of interest and expertise in this area, we are first and foremost humans, and have our own personal challenges and successes that we experience on a daily basis. Recognition of this shared humanity is what brings us together in this very moment. So it is within this context that I introduce my guest for this episode, Jess Fjeld. In so many ways, Jess is someone that I profoundly admire. She is a poet, having published several works, including the highly acclaimed Redwork. She is also the Assistant Director of the Cyberlaw Clinic at the Berkman Klein Center, and a Lecture at Harvard Law School. More importantly, Jess is also a cancer survivor, and was kind enough to share her recent battle with cancer during this conversation. Jess and I also talked about AI generated art, regulating big tech, and considerations for governing artificial intelligence. All right, let’s do this. Jess thank you so much for joining me today. Welcome to “Convergence.” How is the summer treating you?

Jess Fjeld  02:15

Oh, the summers treating me so good. I’m a New Englander born and bred so I’m like, I can never pick my favorite season. It’d be like picking my favorite child. I love each of them for their own unique special qualities. And I love the summer.

Oladeji  02:34

Yeah. It’s just you know, for me, I just think of the Charles [River] in the summer and it’s kind of like, it’s a magical thing to just witness all of, from the winter — and, dare I say, being able to walk on the Charles because of all the ice and the snow — and then and then just months later, the natural beauty of the Charles just flowing forth. It’s it’s yeah, it’s a special transition.

Jess  03:02

It really is not to mention, like, the produce. I ate a nectarine at lunch today. And it was just like a revelation. It was so good.

Oladeji  03:11

So, so I love fruits, fruit, I’m obsessed with fruits. And right now, I’m getting like papayas, cantaloupes, mangoes, pineapples, it is, it’s a dream. So I’m with you. Now is a magical time when it comes to produce. And

Jess  03:31

It really is.

Oladeji  03:33

So I would say we’re witnessing another, It’s not just a seasonal transition, but it’s also a transition of eras, maybe — I would like to think, fingers crossed — from this pandemic into something new. And Boston’s definitely reopening. I think California just, or is in the process of being fully reopened. I know that Chicago is fully reopened, and I was a bit curious to just hear from you, over the past 16-ish months, something you didn’t know about yourself before the pandemic that you you now have learned.

Jess  04:20

Yeah, well, I hesitate slightly, but I’m just gonna do it. I had a different pandemic experience than most people had, because something that I didn’t know about myself at the beginning of the pandemic was that I had colon cancer. I was diagnosed last summer. And it really impacted, I think, you know, the New York Times earlier spring published that article about like, languishing, you know, this kind of like, alienated, bored experience that people were having where they were, you know, it was both a kind of high attention time but also like everyday had a sameness. And because I was ill, I did not have that experience. My pandemic very much had mountains and valleys to it. The treatment now for colon cancer is a, they call it a total neoadjuvant regime. So rather than have surgery first, I did chemo first. I did that last fall, and then December to February, I did radiation. And then I had surgery in March, and very happy, this is a nice time to talk about it, actually, because last week, I had a meeting with my oncologist after having a set of scans and I am cancer free.

Oladeji  05:32

Oh my goodness.

Jess  05:33

The arc of the last 16 months for me was just really different than it was for most people, fortunately, with a happy ending, at least for now. And also, I think, in some ways, interesting, you know, you and I are co-workers in the clinical program at Harvard. And I think that if not for the pandemic, I wouldn’t be sharing this news with you now. But most of our co-workers don’t know, because everyone was remote. I could, you know, even when I was in the thick of chemo, if there was an event that was particularly important to me, I could nap up until five minutes before and roll over and turn on my laptop with video off and sort of be there. And so I had like, the least FOMO cancer experience because while I was home, you know, because of the pandemic, but also because I was ill, everyone else was stuck in their houses to no one got to do anything without me.

Oladeji  06:28

Yeah, wow. Well, you are so courageous. And that experience is not easy. And I have such tremendous respect for you. Thank you for sharing that. I’ll share that my my brother also had colon cancer. And it was very late stage you. Could I, do mind sharing what stage you were diagnosed?

Jess  06:54

Stage 3.

Oldeji  06:55

Stage 3. wow. Wow, wow. Well shout out to you. He, he was stage four. And he went through chemo/radiation for about two years. And unfortunately, he didn’t make it out. And yet, you know, I got to live with him for—very few people actually know this, so I feel like the pandemic is I’m getting the sense that the pandemic has, is giving us space to be genuine, whether it’s like mental health,

Jess  07:32

That’s true.

Oladeji  07:33

Right? Whether it’s mental health or physical health issues. And that’s something I’m really hoping that we hold onto, for the foreseeable future, to let people know that we’re more than just like how we present in work. We’re more than, we’re bringing so much to the table than just nine-to-five or whatever flex-work situation you have. And I was really grateful because for for him, I got to spend a year living with him. And the courage of anyone and keep going through chemo, it wears and tears on you, and it’s very rare that, at least he, was excited or looking forward to the next session. And, and he stuck with it, right? Like he kept going. And there’s just a certain level of nakedness  almost, like you’re stripped down a bit and to still be sincere and battle through all the doubts and all of the pain. Yeah, it’s not an easy process. How How were you mentally going through things?

Jess  08:56

Well, first of all, I’m so sorry to hear about your brother’s loss, and so glad that you were able to be with him in that time. I’m sure that he felt your support acutely, because you’re right, it was it was such a challenge. It is such a challenge. And so many people are going through it now. And I’m glad in some ways that we have this public forum to talk about it. I think you’re right that the pandemic did strip us bear a little bit where, you know, we couldn’t hide. There are things we could hide, right like my, my illness. Many of my colleagues didn’t know about it just because I didn’t, no one was at work. So it wasn’t noticeable that I wasn’t there. But in terms of our reactions, our struggles through this incredibly traumatic time, we couldn’t hide them. But colon cancer is something that people don’t talk about anywhere near enough. It’s incredibly common. It’s becoming way more common among young people. And unfortunately your brother is much more typical of a patient than I am because, I talked to my doctor about this and you know, Chadwick boseman, died not long after I was diagnosed. But most young young people are getting it at higher and higher rates and most young people are not diagnosed until the disease’s metastatic because it’s those full body symptoms that they start to notice. We are all too likely to do so like a) we don’t want to talk about bowel stuff, and b), we’re all too likely to dismiss it as IBS or whatever. So yeah, let this be a PSA to all of your listeners. If there’s anything weird going on, just go talk to a gastroenterologist. Colonoscopies aren’t fun, but they’re way, way, way better than the alternative, if God forbid, something’s happening. So, you know, I think I was really lucky to have an incredible support system in my husband and my kids and my parents and his parents. They really pulled together for us as well as our friends and wider family and community. I couldn’t, for someone in a really shitty situation, I couldn’t have been better supported. And I think, you know, you asked me, you posed this question like, like, what did I learn about myself? And I said, sort of a little jokingly, I didn’t know that I had colon cancer. But I also, I think a big part of the way that I was able to work through it for myself, was that I, I’ve always been a kind of like a yes person. I love a challenge. One of my former bosses jokes that my spirit animal was like a Collie, like a working dog. Just like, I’m always I’m down for anything. But being ill I just didn’t have that capacity anymore. Right. I couldn’t juggle 13 different things at the same time. And so I had to really get serious about what are my priorities? What are the things that I’m unwilling to compromise on? And then what are the things I’m going to just let slide. And I’ve never had to kind of come nose-to-nose with that before. And I think it was really good for me. I think it was, I mean, it was deeply humbling, and incredibly challenging. But I think it brought a lot of things clear about where I want to put the limited time that I have on this planet, what I want to invest it in.

Oladeji  12:13

Yeah. So those moments really highlights how life is so fragile. And you know, for me, before my brother was diagnosed, I was I felt invincible, and I thought, he was diagnosed when he was 32. So I viewed him as invincible, and, and I thought I was invincible and spending time with him and seeing the ebbs and flows, the highs and lows, gave me such profound appreciation for life, in whatever form it is, even if you are you just got out of chemo, and you don’t want to see anyone, you don’t want to talk to anyone, there’s no smile, you just want to go lay in bed, versus like being full of energy. There were times where he thought things were getting better. And there, there was a certain level of exuberance that he had. So just seeing like all of these emotions and all of those experiences in in a short amount of time, it gave me such a new appreciation for life. Like even if I’m feeling sick, or certainly after taking the second dose of the vaccine, I was like, “Oh my gosh, this is awful.” But even in that pain, I feel a profound appreciation for life, whether it’s breathing, anything. So yeah, that that really resonates. And you mentioned your family support, and I am, also this is something that’s really underreported. There’s so many people out there who are going through a similar situation. And I guess I’m just wondering for someone who’s in the middle of chemo, now that you’re on the other side of it, wondering what you what advice you would give that person

Jess  14:30

I would tell them to be compassionate with themselves and this doesn’t apply to you only if you’re going through chemo, but whatever kind of challenge you’re undergoing. I have a vivid recollection of laying on the couch when, on Shabbat, on a Friday evening. I didn’t grow up Jewish but my husband’s family is and you know, my his parents and my kids and my husband are all clustered around the freshly baked challa that my mother in law has made. And there’s, you know, they’re got the [?] over it. And they’re lighting the candles and like thinking to myself, like I could, like it is physically possible for me to get up and go over there. Fridays were also my chemo day, so you know, I’m like back from from the infusion, and really raking myself over the coals for not making the decision to do that. And as I look back at it now, from from I’m feeling much more healthy and strong, I can’t, like, I cannot believe that I was so down on myself in that moment. Sure, it was physically possible. But it was not necessary and the fact that I was having, the fact that I had any instincts that I didn’t want to get up and go over there meant that I was yes, too sick to do it. Like whether or not it was physically possible or not, my body was telling me that I needed to rest. And I wish that I had spent less time pushing back against that, and believed more, you know, and maybe some of it has to do with the, like, the good outcome that I was fortunate enough to have, but I feel like oh, I should have leaned into that time, because it, it was a chapter in a book that is, you know, hopefully, fingers-crossed, knocking-on-wood-like-a-crazy-person closed. But, but yeah, I think I think I was too rough on myself. I expected too much of myself. And it was, it was a real lesson to learn to step back to do less, that healing takes time and energy and investment and has to be a priority in-and-of-itself.

Oladeji  16:51

Yeah. Self compassion in so many ways, is such a powerful principle. And I think it’s easy to overlook, even when you are going through life-changing experiences. And so hearing you say that, I hope more people, regardless of their situation, you know, recognize the importance of being compassionate with themselves. And for you, you’re you’re an amazing person, right? Like you have a lovely family and then working at the Berkman Klein Center at Harvard, and then the Cyberlaw Clinic and you’re also secretly a poet. And I can, I can completely understand with with all you’ve you’ve done wanting to do more, and that friction in that moment of wanting to do more, your body saying no, let’s take it easy. And that can lead to less compassion with yourself. So and I think many people that would resonate with them.

Jess  18:02

Yeah, I think that, you know, that we do we live in a time where there are so many possibilities for connection and learning, so many social issues, social justice issues that our faces are, you know, rubbed right up into, you know, with the protests against the police murders of black people and systemic racism more generally, with the anti-Asian violence, you know, with like, really cogent critiques of the problems of capitalism. There’s, there’s no shortage of things that can demand our attention at this time. And so I think, you know, we’re all in a position for better or worse of having of having too many things that we could invest in. And I think unless we develop the skills to prioritize among them and pick our own battles, right, if we try to fight on all those fronts at once our attention is divided, we end up kind of—you know, I think the app that gets the the wrap for this is Twitter, although I don’t think it’s fair to put it squarely on on Jack Dorsey’s shoulders alone—but like we ended up kind of like flitting from issue to issue right? From thing to thing, and not being able to invest in any of it. And so I do think that that the ability to say no to rest when you need to rest, and then to pick judiciously, the things that you are going to invest in, is just is really key to having a life that’s impactful, and also one that’s rewarding.

Oladeji  19:44

Yeah. Yeah, there are so many things competing for our attention. And if if we’re not really thinking judiciously, as you put it, about what should take up our time, we would just be chasing the next big thing. It reminds me, so Seneca wrote this short philosophy piece on called “On the Shortness of Life,” and he said—and I actually read this while my brother was going through chemo—and he said, it is not that we have too little time, but that we lose so much of it. And that that really resonates with me. Like, there’s just so much out there that we can think of doing and want to do. And if we don’t slow down, and ask ourselves and explore, like, our deep desires, we’ll just be chasing different things. And, and we, we don’t like time is so precious. Every moment is so precious that we don’t, we shouldn’t want to sacrifice the thing that is the most finite in my opinion.

Jess  20:53

Yeah. And I think, you know, it’s interesting, this, I know, you talk a lot about tech in this podcast. And you know, I think that the, we are also in this time where we have we carry these like incredibly powerful computers around in our pockets, and because of the way that that the industry around, you know, technology has evolved, there’s a lot of people you know, to to Tim Wu’s recent book was called The Attention Merchants, right? Or actually, I was reading a really great book last week by this guy, James Williams, that’s on a very similar topic. It’s called Stand Out of Our Light, a sort of more philosophical take on the same issue and the consequences of the kind of endless timeline scrolling. I made a decision about a month ago to delete most of the social apps from my phone . . .

Oladeji  21:50


Jess  21:50

. . . . because of my Apple screen time report. But it’s funny for me, because there’s a really big contrast between how I felt about those apps, when I was mostly sick, right, mostly stuck at home sort of before this, like slow transition out of the pandemic. They were really like, they were my social life and a lifeline in a real way. And like and Twitter was a professional, like, allowed me to continue to engage in professional conversations. And they were really important. And my phone was a real, was a friend when I you know, because I was sick at a time when I couldn’t have friends come over and you know, sit by my bed when I wasn’t feeling well. It wasn’t safe. I was immunosuppressed. And you know, before the vaccines and all of that. So I think it like really shows me how there is not ever going to be like one right solution for everyone. Because a few months ago, I wanted and needed those apps, and they provided me a lot of value. But in the past month, since I’ve been feeling better and you know really back at work full time, having deleted them, I’m finding that moving away from the kind of timeline bite size updates is making a kind of mental space for me to reflect and deepen my own work on the things that I am mostly focused on and to divert attention away from from spending it you know, staring at, staring at a little screen. These these precious moments that we’re wasting in Seneca’s words.

Oladeji  23:19

Yeah, yeah, that’s, that’s great. And, yeah, I think you’re touching on something so important. It’s it’s really context specific. It’s like, at certain points in your life, especially if you’re dealing with a certain amount of isolation from others, physically, social media can be really powerful to promote greater connection. And then in other circumstances, it could be like wait a second, I need to slow down and I need to just eliminate some of these things. And I think sometimes with how big tech is kind of structured, I don’t want to rail on Jack Dorsey or Mark, but it is always at our fingertips. And it can be really hard to say okay, I’m just going to try something out for a week, which is no social media. And and I think being comfortable and just taking that step even if it’s for experimentation or for a more permanent lifestyle, I think there’s a lot of value there.

Jess  24:27

Yeah, you know, I didn’t like I didn’t think about it in a kind of concrete terms before I made the decision. I sort, I had gotten one of my screen time reports and it had gone up and I was like, “What am I doing for three odd hours a day?” Like what is this event what value is this bringing to my life? And I haven’t set hard rules on it so like occasionally you know, I have some people that I messaged with on Instagram o n and in dialogue with others, but there is also a real value to having reflective space where you are not in conversation or you’re not in a broad conversation, you’re in conversation with yourself and with, you know, perhaps a selected group of intimates. And that’s just not you know, I think these companies, I’m like, I don’t know, if I’m a tech optimist or tech pessimist, I think I’m just like more of a tech like realistic, because I do find a lot to appreciate, in, in the ways that the internet connects us and have since I was a kid, but right now the like, the main metric that they they’re, you know, they’re good people who are working hard, they’re working hard to do well, as they understand it, and the main metric is this, like, eyeballs-time-spent-on-platform-metric. And that just, you know, I think, if this industry is going to serve us better than it’s serving us, now, we’re gonna have to figure out new value metrics to substitute for that, because because just, you know, I, I can provide this feedback to Jack and Mark that like the time spent on platform doesn’t feel does not feel aligned with my values. I don’t, it is not better for me to maximize the amount of time spent on Twitter. It definitely raises my blood pressure. But on the other hand, I don’t want to give up Twitter. I do find it a valuable way to connect with colleagues.

Oladeji  26:21

Yeah, yeah. And so it to me, it’s also like, what’s the end game, or what’s an end goal that they would be that Mark and Jack would be satisfied with. And one of the things is, you can say, screen time. Or you could say like fulfillments, and, or quality time. And I think that if some of these big tech companies are probably going to have greater longevity, they’re going to need to change how they think about interacting with stakeholders, and especially customers. Because right now, it’s only a matter of time before people are like [?], maybe the optimist in me is going to say that it’s only a matter of time before people will look at their data about how long they’ve been engaging with these platforms and may like, whoa, that time flew by so quickly, and I got very little out of it. Versus another scenario that could be a possibility, where it’s that time didn’t fly by quickly, but I got so much out of it. Really engaging conversations, and a 10 minute 10 minute interaction on something like Clubhouse felt really fulfilling and satisfying versus two hours trying to find something interesting that someone I don’t know said on on Twitter or something. Well, we’ll see. It’s, I’m trying to be optimistic.

Jess  27:57

Yeah, actually, I went to a great panel today that was hosted by the Initiative for a Representative First Amendment, which is directed by my colleague Kendra Albert. And it was called “Black to the Futures,” about afro-futurism and policing and Bennett Capers, who is a scholar and attorney and all around wonderful human being, wrote this piece on his sort of hopes and dreams for for policing in 2044, which I think is the year where the US is anticipated to be majority minority. And a lot of it revolved around the use of technology to make policing better, which feels kind of wildly optimistic to me and I found myself kind of like wanting to reality check him as he talks about like, oh, you know, like facial recognition could be used to make to like actually decrease bias in police stops because you know, like, it could show that like, that person is not actually the suspect that they’re looking for. So they won’t pull that black guy over he’s just like innocently driving down the street. And I’m like, well, do we know that like examples so far like the examples of like the black guy who did literally nothing and was like misidentified by the system, anyway? Yes, there are these reasons to be skeptical, but I also think like we have to dream big right? If you don’t, if you don’t dream, the like big beautiful positive dream, there’s no way we’re getting there, right? You have to you have to you have to have your hopes. So I hope you’re right about the about the social media networks.

Oladeji  29:24

Yeah. And you’re touching on something so important, which is like people who are engaging with this, especially the the content creators, and also like the developers and the system design thinkers need a certain amount of like, aspiration behind it. To me, I’m really excited about this transition away from shareholder-based capitalism and more stakeholder-based capitalism, where more people are part of the conversation. And my aspiration is what is defined as value to the marketplace, whatever that may be, is more inclusive in the voices that are represented there. I once again, I’m probably I’m probably revealing my naïve optimism. But I’m chugging along. I’m chugging along.

Jess  30:14

You know, I just I think like the world would be so much less interesting without naïve optimism.

Oladeji  30:19


Jess  30:21

I think, yeah, it gets a bad rap these days. But like, it’s not fun to be cynical.

Oladeji  30:26

Yeah, it’s not, it’s not. And like, I don’t get any enjoyment from working with or befriending people who are non-stop cynical like. We need to aspire for some, there can be bad things presently, but it’s important that we don’t lose the creative, aspirational piece of humanity. Which leads me to your poetry [chuckles]. So, I’ve, I’ve just been so fascinated by you, Jess because you’re a lawyer, you’re a law professor. And you haven’t let your law school upbringing, if I may, eliminate or reduce your creativity. You’re still engaging really sincerely with poetry. So I was just curious to hear about, like, what your experience has been as a poet while being a lawyer.

Jess  31:30

Yeah, so I think I was fortunate in that I was a poet first. I did my MFA in poetry. I mean, I had been writing poetry since I was like, in elementary school, I think I figured out when I was like, in fifth grade, I had a really, I had a great English teacher, Susan Metalio, who would really would let me get away with writing poems, instead of really doing my spelling homework, as long as I like worked in some of the spelling words into the poems. And, you know, talk about a way to motivate a student, like, let them let them adapt the assignments to be something that they truly care about. It’s something that I actually really try to push on our Cyberlaw Clinic students, when they’re writing papers, or choosing paper topics for the clinic seminar. I’m like, really, you know, try to write the prompt as broad as possible, so that you can pick a topic you actually care about. Because I’d so much rather read a paper that’s a little bit outside my area of expertise, but something you deeply care about, than, than you trying to sort of produce whatever 5000 words that that you think I’m going to appreciate. But yes, I’ve been writing poetry for a long time, and have been, I worked in book publishing right out college, and then got this opportunity to go to UMass Amherst, and run the poetry magazine Jubilat, which is just wrapping up, like many decades, wonderful run. It was at the time in the like, early 2000s, just about as coolest as poetry magazines got, in my opinion. So I was the managing editor there. And that gave me a fellowship to do my MFA at UMass. And most poets, most of my friends who are poets, or many of them support themselves by teaching, you know, teaching poetry, and I got a chance to try it out. And I just, it really didn’t resonate with me. I found it extremely, I found it very challenging to deal with, like 19 and 20-year-olds. And I also felt it I was sort of crushed, because I would like put together this syllabus of just like some of the best books I’d ever read and bring them in for class discussion, and they were like, I don’t know, I thought it was kind of like, weird. And I was just like, oh, my god, just tromping on me. And so, so I kind of was wrapping up my MFA. And I was like, what am I gonna do next, and Jubilat actually published a lot of found materials. And also, you know, did a lot of contracting with all of our contributors. And so we sort of had consistent legal needs. And it was something my, my grandfather and my great grandfather were both lawyers in rural Vermont, and had really served their communities and I was like, hey, you know, the arts is a community I care about. Maybe if I became a lawyer, I would be able to, to really be of service in this space. And then I think just based on kind of the age that I was, and the needs that the organizations that I ended up working for had and the overlap between the arts and tech in terms of the relevance of intellectual property law, as I worked, you know, on building expertise in the arts, I also found myself building expertise in tech. And so for example, I, after a stint at a law firm I worked in the legal department at WGBH, is the public media station in Boston. And while I was there, I worked on the American archive for public broadcasting, which is a joint project between GBH in the Library of Congress to preserve and make accessible as much as possible of our like incredible heritage of taxpayer funded public media materials dating back as far as like, public radio of the 1940s. And there’s so many gems in there. It’s really just incredible. All kinds of stuff on the civil rights movement, incredible interviews with writers, but also really huge, really huge IP issues with all of this old material with incomplete legal files. And so the Cyberlaw Clinic was actually, we were a client of the Cyberlaw Clinic. So that’s how I came to know it first, as a client, and then ended up moving across when when there was an opening that was a good fit for me. So I have sort of like wandered between and betwixt things. I’ve had a career that I think, well, few would have seen as likely at the time that I was building it myself included, sometimes I say I like fell through open doors that looked interesting. But I think as challenging as it was, I think there was a real balance to it. For me, I think I wouldn’t have been happy. Just as you know, quote, unquote, just as a poet, I think when I started studying for the LSAT, back when I was doing my MFA, like, I really found myself like loving the logic games, I think, I really appreciate being able to exercise my brain in many different ways. And I’ve actually just, I’ve just pitched a reading group and it’s gotten approved, I’m going to teach a reading group next spring at HLS, where I’m going to, with with the law students that sign up, we’re going to read some poetry and really think actually, about how poetry can help us consider not only the substance of serve justice.

Oladeji  36:36


Jess  36:37

And right conduct and our calling as a lawyer, but also how we think about what it means to think like a lawyer, right? It’s something that they often say law school teaches you to do. But what is it to think like a lawyer? What is it to think like a poet? What is it to think like yourself, what do you think like, if you are left to your own devices, so I’m really, I’m really excited. It’s something I’ve done some reflecting on, but I feel like as a class, we’re really gonna be able to dig in and get somewhere.

Oladeji  37:06

So Jess you’re basically saying, you’re telling me that I should quit my job and re-become a student. So I can take this reading group, because that sounds that sounds amazing, basically, exploring poetry, law, and I’m, knowing you, I’m sure you’re going to incorporate technology into all of it. And I feel like there’s such a great need for expanding what we consider thinking like a lawyer is. The history of that phrase, thinking like a lawyer, I think is really one dimensional. And that reading group, to me just sounds like a great opportunity to introduce more ways of thinking like a lawyer, other ways that, that new disciplines or previously unconsidered disciplines inform what it means to think like a lawyer. That just sounds amazing.

Jess  38:03

Well, you should come you don’t have to . . . and I’m pretty sure I’m the instructor. I think I get to say, who can come. You can definitely come. So, yeah, I think it’ll be I think it’ll be really interesting. And I couldn’t agree with you more about thinking like a lawyer. I think, oftentimes, the kind of legal culture that like particular orientation of law schools, and frankly, the legal academy is deployed in a way that is exclusionary, right, but the way that like, quote, unquote, like the stereotype of thinking, like a lawyer, is this really, oppositional, argumentative, classically rational way of thinking, but, you know, at the risk of, you know, I don’t want to go too far, but like, eyes to white supremacy, right. Like it has aspects of white supremacy culture to it. I’m not saying that that’s the only way it can be deployed. I think that there are many examples in history of people who have deployed that kind of thinking and argumentation to a social justice benefit. But I do think that we do ourselves a disservice as educators and as a legal profession, if we don’t make space and acknowledge during law school and throughout the profession, but there are many ways that people can bring and add value to this and that not everyone has to be a legal academic or an appellate litigator, that there are lawyers who are conveners who are people people who are experts at dispute resolution, who are business people and entrepreneurs, and and who are artists, or filmmakers or and that all of those are legitimate and important ways to quote unquote think like a lawyer.

Oladeji  39:53

Yeah, I am sold. You got me.

Jess  39:56


Oladeji  39:58

100% that’s, that’s exactly it. I’m so excited for the reading group, I’m glad that you’re going to be leading it. And I’m excited to just see how students engage with it, it’s gonna be great, I’m gonna start recruiting my students, then you got to take this reading class. And in your writing, for me, in your legal research and writing, I can see the creativity in it. You, you, you wrote something about AI-generated art, which to me sounds so fascinating, because with the use of AI and online dispute resolution, some people kind of a common critique is that to manage and resolve disputes, you need some level of creativity, which, which I think is true. And so I kind of just wanted to hear from you on AI-generated art, because to me, it feels like that’s a creative thing that artificial intelligence is dealing with.

Jess  41:09

You know, it is a creative thing that artificial intelligence can be involved in. But I think that dealing with may go too far. So I think I think there’s a bunch of really incredible interesting AI art that is being created right now. But I really think of it more as artists, human artists, using machine learning algorithms, in a way that like looks a little different, but is not actually fundamentally dissimilar from how a musician uses a guitar, a photographer uses a camera, right? It’s another machine. It’s another composition technique, another tool that lets humans express their ideas. So if we’d like just take visual art finders are as an example. There’s these technologies called GANs, generative adversarial networks . . .

Oladeji  42:03


Jess  42:03

Where you have one out of two paired algorithms, one of them generates images. And the other one sort of judges those images against a predetermined set of images to say, like, does this, you know, does this sort of rise to the standard that we’re expecting for an image of the output type we want? Yes, or no and, and they sort of go back and forth until it gets to a good enough image. Most of the artists who are making cool work with GANs will tell you if you talk to them, that they are producing vastly more images than the ones they’re eventually sharing as outputs. So essentially, what this is doing is like giving artists you know, they do they do a bunch of work, first of all upfront to find the parameters that the the GANs will work on to determine what the training image sets will be comprised of, which is going to determine what the outputs look like. But then they also do this aesthetic work on the other end to select among the images that are, you know, to sort of separate the wheat from the chaff, and then also, to title and and intellectually, aesthetically situate the work to say, you know, what is this saying, why is it important? What does it mean? That, as far as I’m concerned, like, no AI is like anywhere close to doing and based on the technology that we have now is unlikely to be able to do.

Oladeji  42:04


Jess  42:30

They do they they stumble across gems, but it’s more like Jorge Luis Borges like infinite library, right?

Oladeji  43:41


Jess  43:41

Like, it’s like, there’s a book with every possible combination of letters on a set number of pages, that is the space in which AI is can be creative, because in a library like that, there would be some volumes that were Shakespeare or Toni Morrison or whatever. But it would be by accident, because there would be many, many more volumes that were just complete nonsense.

Oladeji  44:04

Yeah, so that that makes a lot of sense, because in the AI ODR realm, people use the term AI ODR as the fourth party. So you have like the disputing parties parties one and two and then you have the mediator arbitrators the third party, and then you have the AI ODR system, providing as the fourth party providing supports to the third party and the third party has still a significant role in the process. But you have the intelligence, if you will, of AI, using its comparative advantage to identify trends from large data sets, and using that to better inform the alternative dispute resolution practitioner to make decisions to better understand the context that the disputants are, are involved in this mediation. So it to me it sounds like there’s actually a clear line between how AI is being used in arts and the supports that AI provides to artists with AI’s use in online dispute resolution and the support AI provides to, to third parties.

Jess  45:27

Yeah, I think that’s just right. And I think it actually, it goes to, you know, AI, artificial intelligence is like, is a really big umbrella term. And there’s this like, classic, you know, statement that the definition of AI is whatever we thought computers couldn’t do. And so you know, because there’s, like, if you think back to the 60s, things that they would describe as AI now, you know, you could probably program a calculator to do, they’re like, they’re pretty simple from our current way of thinking, but at the time, they were groundbreaking, and they are considered AI, but the, you know, the technology that has underlaid, most of the quote unquote, AI developments of recent years is machine learning, of course, which is fundamentally a pattern recognition technology. And so it makes a lot of sense to me that that is kind of has a role as the fourth party in AI ODR, because it can look at these big data sets and say, oh, actually, you know, when, when people are disputing for like, you know, approximately this amount of money and there’s something about like, whatever a vehicle involves, actually goes this way, usually, and they might spot a pattern that based on that larger data set, the the professional the third party wouldn’t have. And similarly, I think young American like coder, an artist named Robbie Barrett has done a lot of work with GANs training them on like, classical Western art works, mostly paintings, and they produce these kind of like, sumptuous forms, but non-human forms, right. So that the AI there, the machine learning program is recognizing these like rich colors, and skin tones and these kind of rounded shapes. But it’s not interpreting the like parts of the pattern, but a humanizing key, which is right, like you need like a recognizable body. And so it has both the possibility of giving us this thing that feels really fresh and new and kind of exciting. And, and that kind of new insight, but also the possibility that it just produces something that’s like fully off base, and not interesting, right? Like, like that classic example of now classic, that’s only a few years old of like the hiring algorithm that looked at the resumes of like people who had previously succeeded at Amazon, and was like, oh, you know, what you need to do to make people succeed is hire men. Right. So like the AI, these machine learning networks, they don’t have value judgments at all, they just evaluate patterns that exist in the data. And so they’re very suited for some purposes, particularly when they’re paired closely with a person who can bring that judgment to them, but deeply unsuited to other purposes. And, you know, from talking to technologists in this space, I think that it’s not entirely clear, what field of computer science is, is likely to yield up anytime soon software that’s really going to be able to exercise judgment, the way that that humans do.

Oladeji  48:23

Yeah. So you’re touching on something that I think is just so important, which is the shortcomings or the imperfections of AI. And I think broadly, there can be two camps. And then a third camp that I would say that I’m in with you and one camp is kind of thinking that AI can just completely replace human decision making. And I think there flaws there because of the problems you’re describing. There’s even like the concept of the garbage in, garbage out where if you have poor data sets that are given to the AI, then you are going to have bad outcomes, bad outputs for parties using it. And so that’s one camp. And then I would say another camp that I also am not in and I think you’re not also in is one that says there’s no value at all in artificial intelligence. One you could say because the human capacity is just so great that it doesn’t need any assistance in decision making or an understanding large datasets and I think there’s a shortcoming there as well, because it’s it’s more in this goes to the third camp, that I think we’re both in that I know that you are in, which is how do we govern these systems better, so that we aren’t advocating complete decision making to it, but we are least engaging with them in a way that they can bring their comparative advantages in a way that isn’t dispositive, but just in a assisting way. So sorry, that’s a mouthful. And so I kind of just wanted to hear about the governance piece because it is so important if we’re deploying artificial intelligence in so many ways, it’s really critical to have the proper guiding principles and the proper framework for it. So how do you think about AI governance?

Jess  50:28

Yeah, well, I mean, like three or so years ago, I had thought about it not at all. And then the Berkman Klein Center in conjunction with the MIT Media Lab got a grant to do a kind of intensive research sprint over a couple of years on the ethics and governance of AI. And so I started tuning into it, and it was right at the time, kind of 20, early 2018 that no, maybe even yeah 2017 where all of these principles documents for AI were starting to come out, it seemed like every organization was producing with any interest in tech was producing an AI principles, whether it was private companies or NGOs, and I felt some whiplash going, you know, sort of having all these come into my inbox and going between them. And you know, were they saying the same thing, were they saying different things, some some words seem to be recurring, other ones seemed like the vocabulary was different. And the outcome of that conclusion was a project that we called principled artificial intelligence, which was a study of 36, prominent AI principles, documents, which were as diverse as we could make them across stakeholder group geography, time and other factors, while sort of emphasizing the documents that were among the sort of leading documents in the field that were likely to be kind of touch points for readers. And together with a really incredible research team, including Hannah Hilligoss, Adam Nagy, Nele Achten, Madhu Srikumar, and others, we coded these documents, and then did an analysis of them to kind of understand whether there was there were kind of key things emerging. And I would say, we did identify key themes, including bias and nondiscrimination, fairness and nondiscrimination, which was represented in every single one of the documents, the only theme that was represented in every single one of the documents that we looked at, along with things like privacy, transparency, and explainability, human control of technology, the promotion of human values, and more. But the other thing that that work uncovered was that in spite of, you know, putting together a very multilingual research team that came from all over the world, we were not able to locate any documents that met our definition of AI principles from the entire continent of Africa. And there are a couple of African governments that I know have AI principles, documents in the works still at this point that we knew even at the time, like the Kenyan government was working on one. But what that taught me was that, you know, in some ways, there was a conversation that many were inclined to describe as, like maturing right around what these core values were in the governance of AI, but that we were also, you know, if if we allowed that, to be kind of the end of, of the sort of creative piece of the conversation around AI governance, we are going to really fall short, because the people who are likely many of the people who are likely to be most impacted by AI, were not yet part of the governance conversation. It’s a criticism that the human rights standards are often levied at human rights standards, because they were sort of drawn up primarily by folks in the West and then deployed on folks in the majority world. And with AI, I, you know, I think of AI in many ways as being primarily an efficiency tool, right? It allows, whatever a person or an organization is doing, it allows them to do it faster and bigger. You know, whereas in social services, if you have one caseworker, if you were, you know, program and AI to replace that caseworker, it can go through a lot more cases than she ever could in a single day. And that means that marginalized groups are likely to suffer the impacts of AI, more pronouncedly, because that’s where governments, organizations, companies look for efficiencies first. And so it becomes really important and has been kind of the focus of my work since the publication of that paper to think about how can we make the AI governance conversation more accessible? How can we lift up voices of marginalized folks, indigenous folks, impacted folks in this conversation and really ensure that they play a key role in in setting out what the governance should be?

Oladeji  55:04

Yeah so first, I’ll just say that your work and your team’s work with principled AI is amazing. It’s just even from a design level, the charts you use and the representations you use. It’s beautiful. And then on a substantive level, it is so important. And I think, well, so if my knowledge serves me, correct, this was published, maybe like a month before the start of the pandemic, right?

Jess  55:40

Yeah, January 2020.

Oladeji  55:42

Yeah, so, so an odd time to publish. And I’m sure, no one could have expected what would start happening a month or two later. But on a substantive level, I think the paper is just phenomenal. And many conversations around AI governance, in recent history, have been more focused around kind of the stakeholder engagement. And stakeholders usually I don’t want to throw shade on the past. But to me, stakeholders  . . .

Jess  56:22

The past is a pretty shady place.

Oladeji  56:23

[Laughs] Thank you. Yeah. Usually like the the stakeholder definition is pretty limited. And so I think it’s critical. The approach that you took, and your team took in this paper, to think more expansively about stakeholders, it may not just be the stakeholders currently engaging with it. But it’s also the stakeholders who in the future, will be engaging with it with the same amount of frequency or even more frequency as some stakeholders are today. So one thing that I was thinking about, so when I was rereading principled AI, because I actually saw it, it was shared with me last year. And so I was rereading it recently, and something that just came to mind was the connection AI could have within the historical context of thinking about the internet. And so recently, I was once again rereading A Declaration of the Independence of Cyberspace by John Perry Barlow. And this is I want to say in the late 90s, early 2000s, Barlow is one of the founding members or perhaps the founding member of the EFF. And one part of this declaration that he wrote was “cyberspace consists of transactions, relationships, and thoughts itself, arrayed like a standing wave in the web of our communications. Ours is a world that is both everywhere and nowhere. But it is not where bodies live.” And then he goes on to say, how we’re creating a world that all may enter without privilege or prejudice accorded by race, economic power, military force, or station of birth. And well, first, I just love that segments, because to me, the aspirations of the internet and technology is more inclusion. And he identified that from a early moments in the internet’s history. So I was I was a bit curious just how you think, potentially the relationship between his conceptions of what the internet could be or would become, versus how you’re thinking about principled AI in terms of like, where more people are involved in the process?

Jess  59:01

Yeah, thanks for quoting from it, I feel like it is, in many ways, a moving and beautiful piece of writing, although when I come to it, now, I often come to it with some sadness, right? Because it’s, you know, it’s that’s not the internet that we have, you know, from the Great Firewall of China to Christchurch call after the massacre in New Zealand.

Oladeji  59:26


Jess  59:27

There’s some, there’s some horrifying stuff there. So, you know, I think it articulates a beautiful dream and a dream that I think has had glimmers of reality here and there. But to me, there’s a there’s a sort of fundamental flaw in the logic behind it, which is also the flaw behind people’s expectations that AI or any technology could sort of solve the problems of the world and it goes to that, you know the difference between equality and equity, which is that I think that the Declaration of the Independence of Cyberspace and Barlow’s kind of thinking generally, although I, you know, I didn’t know him and, and others who know him better may dispute this, and I would welcome that. But it comes from a time of sort of free speech maximalism when the thought was, you know, if you just give everyone a platform, then everyone will be heard. And I think that what we understand now, with a with a better sense of how social justice split issues play out systemically is that, you know, one person’s platform is another one’s like hate speech target, right. And that it is actually it’s not enough, just the same as it’s not enough to just train an AI on all your past hiring data to ensure equitable outcomes, right, because your past hiring, it turns out, you know, if you’re pretty much at any company anywhere, like had gender bias, as part of it, you know, it’s not enough to just sort of throw open the doors to the internet, and ask anyone to enter. But increasingly, we’re seeing you know, as, as the internet becomes more and more a part of our life, that we actually if we want to have a kind of utopian community like this, it doesn’t come from less work, lower barriers, it actually comes from intentionally working to build up toward equity, which means providing support, so that, you know, women and folks of color can speak up on the internet without, you know, then suffering an inundation of intimidation, and all around gross interactions, it means working toward ensuring equitable access to, you know, good connections, and adequate, you know, hardware to access the internet, it means thinking about equality around content, moderation, you know, from wealthy countries that use very popular languages to the Myanmars of the world, that there are so many axes along which the same social injustices that exist in our physical worlds are replicated on the internet, and that it takes just as much work to repair them there. And these in these in the context of internet in the context of AI the context of any new technology, as it does to repair them in the countries that Barlow name checks in this place that that, unfortunately, it turned out that the internet was, you know, was was not a new land, it was really just next door.

Oladeji  1:02:54

Yeah, that’s beautifully stated. And so earlier, you use the example of Amazon’s how Amazon used AI and ended up being incredibly sexist. And after what you just shared, it made me think of Microsoft and how they created a AI bots on Twitter and basically, the programmers and developers who were writing the algorithms, it ended up not filtering out bad data sufficiently. And so the bots name was Tay,  T A Y and the bot ended up being incredibly sexist and racist as well. And it was just kind of like, gathering data from from Twitter. So what you share about Barlow’s vision, being beautiful as a vision and not how things have shaped out, I think is right on. And us doing the work to make sure that the systems kind of live up to the aspirations of Barlow is also important. It makes me think of mechanism design where you start in mechanism design is like within the game theory world and it’s like you start with your ideal outcome, and you work your way back. And I think more, well actually, my aspiration is that rather than letting things just flow naturally, there’s more focus on what the end game should be. And we work our way backwards.

Jess  1:04:37

Yeah, someone should put you in charge Oladeji.

Oladeji  1:04:39

[Laughs] Oh, God, no. That would be a day and then I would be out [laughs]. But I’m very excited that there are people like you in charge.

Jess  1:04:54

Oh if I’m in charge no one’s told me yet. I prefer my little perch.

Oladeji  1:05:03

So something that has come up quite frequently in online dispute resolution is making these platforms more accountable. And the hope is that by being accountable, there will be greater confidence and trust in the platform itself. So I was a bit curious like with with all the research you’ve done, how you think platforms can be made more accountable to their stakeholders?

Jess  1:05:33

Yeah, I mean, it’s a great question, I think there’s not, it’s something if it gets a space, where, to my mind, at least, there’s less to be gained from past research and more to be gained from kind of the use of the imagination. But I mean, something for sure that comes up in with the principled the AI research, for example, is that fundamentally the structure of corporations requires them to be profit motivated, right, they’re responsible to their shareholders for the maximization of profits within certain bounds. And so even where they have a drive to do the quote, unquote, right thing, they may or may not feel able to do that thing, absent regulation. So I think that that’s one space where you’re actually seeing some companies and you brought up Microsoft and that like, unfortunate Twitter bot and but Microsoft, you know, Brad Smith has been really out there routinely calling for increased regulation in these spaces. And you know, you could be skeptical and say, well, they’re a large player, they have, you know, sort of an entrenched interest in having regulation at the stage, because they’ll be able to influence the lobbying, whatever. But I think that they also have a sincere interest in sort of seeing the floor raised up. So I do think that regulation will help with that. And I do think that there are companies that sort of see and understand that and actually would welcome it so that they no longer have to feel like their work to make their products and services, sort of more socially beneficial, is a bottom line cost. Otherwise, for overall accountability, it is a little bit hard for me to understand how a company that is that has the size and scope of a Facebook or Google or even an apple is ever going to be truly accountable. You know, they rival governments. Yeah. In their size and influence. And, you know, I think if if accountability were what we were privileging, we would be starting to talk about breakups.

Oladeji  1:07:40

Yeah, well, a bit earlier, Amy Klobuchar, she wrote a book on antitrust and how antitrust kind of needs to be updated to manage the existence we are living in where a lot of these companies are able to peddle this argument of, we’re promoting consumer welfare. We’re not doing it in an anti-competitive way. And yet, when you look at their size, comparatively, they are larger and more influential than the Rockefellers and all of the Industrial Revolution companies that work had to be broken up because they were too big. So I second that, I think, on the consolidation and concentration of power and resources, it feels increasingly untenable to expect such large institutions to even entertain being accountable, when when they just have so much they have so much. And another thing you mentioned with kind of like stakeholder capitalism, I am a bit far removed from my corporations class, to be honest, in law school, but my one takeaway from that was kind of through three cases or two cases. I know that there is like the Revlon case that that said, the sole purpose of a corporation is to maximize shareholder value. And with all that we have experienced over the past few decades, that to me doesn’t really represent I think, where the country currently is in terms of how they engage with these corporations. But I’m not on the Supreme Court.

Jess  1:09:40

Yeah, unfortunately. I mean, I think that I think we are recognizing, you know, and like I think there were moments where this happens, like in the 70s, you know, with the creation of the EPA, that there justice, there are many things baked in to share price, but there remain very significant externalities that companies are just getting away functionally with not dealing with with the current the current corporate structure. And I think you know, as a result, you see a number of companies that do want to take a broader view becoming social benefit corporations.

Oladeji  1:10:13

Yes, absolutely. Yes. So Jess I’ve taken up so much of your time, I truly think that I could speak with you for hours. And I don’t, I’m not exaggerating at all. I think we could talk about these things for hours. I do have one final question for you.

Jess  1:10:30


Oladeji  1:10:30

The ultimate question. And that is what you believe about the future of technology and dispute resolution, or the future of technology and law, that very few people in your industry believe.

Jess  1:10:45

Oh, what a great question. I think I’m gonna like, loop it back to like the poetry thing.

Oladeji  1:10:54


Jess  1:10:54

And say that I believe I think in contrast to many people, many of my colleagues that artists and poets and others who really exercise the creative as opposed to the analytical parts of their brains have a central role to play in the future of law, technology, disputes in really in building the future.

Oladeji  1:11:23

Mm hmm. I love that. And a prior guest, actually, the first guest Colin Rule, who is colloquially, the godfather of online dispute resolution. He he said that he believes courts and dispute systems would incorporate virtual reality increasingly in the short to medium term future. And I actually think that relates to what you just shared, because we have to think creatively about what is working well, for parties. What is working well, for disputants. And, obviously, there’s the price points, right? I, I’m not a fan of Oculus and Facebook. But yes, it’s it’s rather expensive. And Oculus is I think one of the cheaper or maybe even cheapest VR headsets. And so it would be kind of hard at this point for that to be rolled out, especially in terms of like access to justice. But we do need to think a bit creatively about other ways that these parties can engage with court systems and dispute systems and having more poets having more creative thinkers, I think would get us there.

Jess  1:12:39

I hope so.

Oladeji  1:12:43

Yeah, well, Jess I don’t want to take up too much of your time. I’m immensely grateful for you. I think that you in many ways, embody. This is gonna sound very cheesy. You embody the courage that we need, looping it back to the start of the conversation. chemo is not a fun process to come out on the other side is filled with different emotions. And I hope and aspire for more people to have the courage that you have. And also, I would strongly recommend you to write a book or write a poem about some of these things that you’ve been engaging with recently.

Jess  1:13:27

Well, thank you for a tremendous conversation and for that very kind thought. I will I will strive to live up to it.

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