Tackling ‘big tech’ issues through storytelling, with Jessica Powell

Jessica Powell, Google’s former head of PR from 2012-2018 (years in which Google required a not-insignificant amount of PR leadership), is now a rock star writer whose 2018 debut book, The Big Disruption: A Totally Fictional But Essentially True Silicon Valley Story, was the first novel published by Medium.

I recently spoke with Powell for this series on the ethics of technology, because The Big Disruption, for all its manic energy and a playfulness at times bordering on sci-fi sitcom level-absurdity, should be viewed as a key work in the emerging field of tech ethics. In scenes like the one that begins below, her comic timing and characters help us see how “disruptive” technologies may not so much change humanity, as reveal it.

As a product manager, you are tasked with leading a team and bringing an idea to life. You are the visionary who must direct not just engineers but also marketers, sales teams, lawyers, and others. You are a mini-CEO, the ruler of your product!

“Just like king!” Arsyen shouted to the empty stalls.

It’s part Dave Eggers’ The Circle; part “Coming to America” (the classic 1988 Eddie Murphy comedy about an African prince’s incognito sojourn in New York City); and part dystopian Tarzan. In this rather amazing sequence from an early chapter in The Big Disruption, Arsyen Aimo, an exiled prince from the fictional backwater country of Phyrria who has been working in Silicon Valley as a janitor, has accidentally convinced executives at the tech behemoth Anahata to hire him as Project Manager for the company’s disruptive new project – a car slash social network. Now, Arsyen has locked himself in the bathroom to scroll his phone for info on what Project Managers at tech companies actually do.

Of course, there is one important difference: You have no direct authority over anyone, and you must lead through influence.

“Hmmph, more like queen,” Arsyen grumbled. But then he reconsidered: Other than the receptionists, he had yet to meet any women at Anahata. He probably didn’t need to worry about being treated like one of them.

Jessica Powell, of course, was a woman you might well have met at Google, if you’d been working at the highest levels in or around the real-life tech giant over the past decade. While she joins others who’ve left Big Tech to write important philosophical books shedding light on the political and social implications of their industry (James Williams, Chamath Palihapitiya, Tristan Harris, and others come to mind), no one has yet succeeded like Powell in illuminating our current culture of technology. And if we can’t see our own culture, how can we change it?

After the short scene below, you’ll find part one of my two-part conversation with Powell, where we discuss the importance of satire in ethics, and how her background may have led her to become one of Silicon Valley’s most interesting and important class traitors.

Arsyen skimmed a few more blogs, trying to memorize the P.M.’s language — words like “action items,” “B2B solutions,” and “use cases,” and then something mystic called a “roadmap,” which as far as Arsyen could tell had little to do with either roads or maps. There was an even greater obsession with “alignment,” a concept Arsyen struggled with as his translation app told him that the equivalent word in Pyrrhian was pokaya, meaning to place the chicken coop parallel to one’s home.

Suddenly there was a banging on the stall door.

“Arsyen? You in there?”

It was Sven.

“Listen, you’ve been in there long enough. Only senior engineers get to work in the bathroom. Roni has some sort of roadmap question for you, so come on back.”

Arsyen washed his hands and returned to the cubicle, armed with his new vocabulary.

When Roni asked Arsyen about prioritization, Arsyen asked, “Is this on the roadmap?”

When Sven suggested adding images of attractive women to the car dashboard, Arsyen rubbed his chin.

“Does this align with our strategy?”

When all three looked to him for an opinion in how best to implement Symmetry Enhancement, Arsyen stood and put his hands on his hips.

“Does this align with the strategy on our roadmap?”

No one seemed to notice anything was amiss. If anything, it seemed like product managers just asked questions that other people had to answer.

Jessica P.: When you first reached out to me, I knew your name. Then I looked you up, and ended up reading your Wikipedia page and being intimidated.

There’s this amazing line in there, and because it’s Wikipedia, it’s written so straight…something to the effect of, he went to Asia, discovered that actually no one has enlightenment, so he came back to the US and became a rock star. And it was like, “Oh, wait. I can talk to this guy.” It was just so funny.

Greg E.: That made me more relatable?

Jessica P.: It’s just human. It combines so much [about] youth, like, “You know what, I’m just going to learn to play Stairway to Heaven.”

Greg E.: That line may have been up there almost since Wikipedia was invented, and I guess no one has written in to dispute the characterization “rock star,” yet. They would be on very firm ground to do so.

Anyway, speaking of my background, I have so many questions about you and yours. For you to work in such a senior capacity at Google for a long time and then write a book like this is extremely rare. You’re shedding light on so many of the nuances of the tech world that is shaping all of our lives. I want readers to understand more about you, so they can have a better sense of the lens through which they’re seeing your experiences.

So, we’re about the same age: the first generation to experience any kind of mass digital or internet culture as young people. So I’m wondering what it was like for you to come up from a pre-internet childhood, then go to Stanford as all of this was emerging, then help shape it from the inside.

Where are you from? Where were you born and what was life like for you before you got into Stanford?

Jessica P.: Wow. No one’s ever asked me that. Let’s see, I grew up in Southern California in Orange County, which has no particular distinction other than I think it was the first county to ever go bankrupt. Eventually, there was also that show The O.C.

Greg E.: Orange County, to me, means Saddleback Church. Does that have any relevance to you?

Jessica P.: It does. Were you at Saddleback?

Greg E.: I’ve written about them quite a bit, actually. They’re a fascinating community to me: arguably the world’s most influential Evangelical megachurch. How did it come up in your childhood?

Jessica P.: Well, it wasn’t far…I mean, nothing in Orange County is far because it’s a small county, so I always grew up knowing of it. My family is not religious. My mom’s side I think is Southern Baptist, my dad’s side is Quaker, but we weren’t brought up with any religion. So while Orange County is very conservative, a lot of the religious [activity], I was largely unaware of. Whenever I go back there, it’s interesting to see the spread of pop-up churches, trailers, that kind of thing. Church was a much more hum-drum kind of affair when I was growing up.

I was big on, ‘fight the man.’ I wanted to be punk rock.

Greg E.: This is relevant to your current work, I think. I mean, you headed PR for what was originally a counter-cultural company that eventually became as good an example as anything in the world of “The Man.” Now you’re satirizing that company and others like it. So, how were you ‘fighting the man’ as a kid in Orange County?

Jessica P.: Orange County is conservative, but also full of contradictions. Orange is not one of the wealthier cities in Orange County, but the county on the whole is wealthy. I remember being in public school [in the early 90’s], having teachers that had no qualms about voicing their politics in terms of gay marriage, immigration. At the same time, Orange and quite a few parts of Orange County were incredibly diverse. I don’t know what the statistics were for in my high school, but it was, I think, split. I’ll get this wrong, but say a third white, a third or more Latino, and 20% or so Asian-American. Compared to where I live now in San Francisco, where I grew up actually was much, much more diverse.

It’s interesting: I live in one of these super-progressive places where there’s relatively little diversity, compared to a place that was actually conservative, but had a lot more diversity. And I would even say diversity of thought. Most people in my high school were somewhere between lower and middle class, maybe some upper middle class. That’s actually quite a broad swath; you don’t get that every day going to work at a tech company in San Francisco.

Greg E.: Was that helpful to you in your eventual work, in retrospect? To be able to relate to people from different backgrounds?

Jessica P.: I think when you’re a kid, whatever’s in front of you is what you think is normal. I don’t have any level of reflection about it. It would be revisionist to try and claim that it was this wonderful ‘let’s gather around the flagpole,’ like what you hope for today at your kid’s school. No, that was just what you did. You all kind of had the same lack of allowance, just hanging out at the mall, all bored together.

Greg E.: You got into Stanford, and went straight out of high school I assume?

Jessica P.: I did, but I didn’t want to go. This is where I laugh at my radicalism. I thought college was elitist. I had read some Chomsky books, and I thought I should go off to the Chiapas to do some sort of vague fighting on behalf of something…it was never even clear what I was going off to do. My parents told me they would ground me if I didn’t apply to college. It seemed like the smaller battle: whatever, just go ahead and apply.

I applied to a handful of schools. When I got in, I went back through my routine: ‘college is elitist, shouldn’t go.’ My parents were very smart. Rather than fight me on it, my Dad was just like, “Hey, I was talking to someone who did the Peace Corps, and I didn’t know this, but if you want to do Peace Corps, Jessica, you actually need to have graduated from college. So maybe you should just go [to college first].  Or, “Do you have your vaccinations? Here’s the list of all this stuff [you need to do]. Here are the three rabies shots you have to have in your butt.”

I had just enough rage in me to spout political proclamations, but not enough to actually make it happen. Do you know what I mean? I was still, fundamentally, a lazy kid.

Greg E.: Well, you couldn’t have been too lazy in terms of academics, but it was hard to do take such an unfamiliar path, is what I imagine you mean.

Jessica P.: I was also just fundamentally, and kind of still am, a rule follower. I knew you were supposed to go to college. Even though part of me believed there was something unfair about it, part of me was like, “Oh, but maybe I should do it.” That’s my charitable view of Jessica at age 18.

Greg E.: Okay, that’s really helpful to me in getting a sense of your background.

Jessica P.: One more thing I had never really thought about until you asked about it. I genuinely like people, and I think I am a bit of a rule follower. I think I’ve always wanted to belong, to do what you’re supposed to do. But at the same time, there’s always been a feeling of being outside the group, observing it as an outsider, or someone who doesn’t entirely belong, doesn’t entirely agree.

Greg E.: The idea of insiders and outsiders in tech comes up in very significant ways in your book. At one point, we meet Roni, a technical lead on one of the hottest, most anticipated projects at Anahata (Google). A 30-something, slightly balding man whose work uniform involves brightly colored T-shirts with cartoon characters on them, and red plastic sandals, he’s been assigned to this project called Social Car, and he’s probably doing extremely well, making a lot of money, influential, hiring and firing and such. But he’s worried his role itself is not significant to the company’s long term vision, and that means he doesn’t quite belong among the top engineers as he would like to, right?

Jessica P.: Right. Or Jennie (another central character in the novel). Not necessarily that she cares about being a PM or an engineer, more that she wants status, belonging.

Greg E.: And I love what Kara Swisher said in your interview with her: “That is exactly right. That is Google. That is all of them, pretty much.” Swisher felt you really nailed the characters and the general personality of the place. I’ll take her word for that.

Swisher also mentioned that you had taken over what she saw as a really big job from Rachel Whetstone, who at one point had left for Uber. Rachel, by the way, seems to have bounced back and forth from Google, which you have as well.

Jessica P.: Rachel was at Google, then she went to Uber, then to Facebook, and now she’s at Netflix.

Greg E.: I noticed she is a member of the Conservative Party in the UK. How common is that, for somebody working in such a big role, publicly representing a company like Google? I’m picturing you, for example, as somebody who would not be in a conservative political party.

Jessica P.: I’m pretty far left. I’d say it’s not uncommon. Historically, the English conservative movement has been different from the U.S. conservative movement, so you can end up with someone who actually is socially quite liberal. I don’t think anyone would ever say someone like Rachel is socially conservative.

It’s not uncommon to have a [conservative] head of communication, or just communication executives or policy executives…the larger the company gets, the more diversity you need to have in your external facing functions to show you represent both sides of the aisle. So if you look at Facebook, Joel Kaplan, who leads their policy team, is conservative. There was that whole brouhaha with him appearing the Kavanaugh hearing. But yes, most people in tech lean toward the left.

Greg E.: You’ve talked about how you wrote this book while you were between jobs, because you wouldn’t have had time to work on it while you were there. You have three kids. When you took on the really big role at Google, were you already married with three kids?

Jessica P.: I think I had one kid when I took that role, and then I soon had the second, and then I had the third after I left Google.

Greg E.: This is during the time where, as you told Kara Swisher, you really had very little downtime. You couldn’t even so much as go to a wedding without really checking in to make sure James Damore doesn’t send a memo?

Jessica P.: Yeah, I never had a day off.

Greg E.: How is that possible with a family?

Jessica P.: I felt it was impossible. I mean, possible in the sense of my husband is also a parent so he would pick up the slack when someone would call and the kids needed to be watched. He would do that.

Greg E.: What does your husband do? What is his life like?

Jessica P.: He was an economics professor, and now does data science and AI work. It’s much more predictable. It’s not like he’s on call 24 hours a day. If something goes wrong, it goes wrong with his model. He might need to run the model again, it can be very upsetting, but it’s not like you have to all the sudden drop everything and find a babysitter or call your wife to see if she can watch the kids.

[At Google] you’re always on call. At times, you have really big issues that torpedo your entire day, that might have you in the meeting room the whole day. I really tried hard to make sure that stuff that wasn’t urgent, I wasn’t dealing with on the weekend. Not only for selfish reasons in terms of my family, but also because if you’re working on the weekend that means you’re making other people work on the weekend.

Greg E.: In terms of your husband and his ability to pick up your slack, on the one hand, that’s great. This interview is part of a series about the ethics of technology, and to me, balancing the work among couples, and particularly avoiding stereotypical gender roles around work when it comes to hetero couples, is a big part of whatever we want to think of as ethics. But what you had to deal with is bigger than any one family. There is so much pressure in these corporate tech cultures, and also so much sexism.

Jessica P.: There’s no way I could have managed to write a book when I was doing that job. I did start, I think, when I was on my second maternity leave. In between my baby naps, I would try and write sometimes. [I wrote more of the book in] 2012, when I was at Badoo, a start-up. I don’t know if you saw the essay that went with the book?

Greg E.: Yes, the one where you talk about why you wrote The Big Disruption. In print it appears at the very end of the book, but it’s also a great standalone reflection on the excesses of big tech companies.

Jessica P.: It talked about being a moment, at the DLD conference, where it all crystallized for me. It had been building for a while: this sense of hypocrisy between what we were marketing to the world, and what we were delivering. Which is not to say people’s intentions weren’t sincere. I think in some cases they were, but self-delusion.

But also, I think very much heightened by the fact that I was working at a start-up where it was so comically bad, the internal atmosphere, particularly in terms of the sexism. It felt like it didn’t matter how many times, and how many different gentle ways or direct ways you tried to raise the issue, no one cared. No one wanted to do anything about it to the point where I started to wonder if I was, as people suggested, overreacting or misunderstanding.

I think that’s why I started to write, to make sense of this world I had found myself in. The really extreme sexism of the book comes, in part, from that too. Like, ‘how much do I have to exaggerate this for you people to finally agree it’s a problem?’ How bad do I have to make this for you to finally [acknowledge], “Oh, this is misogyny.”

I do think if I hadn’t worked there, in such an extreme situation, I wonder if I would have written this book. I still would have cottoned on to or made fun of the hypocrisy of the larger tech industry, for sure, but I don’t know if I would have had the same level of rage and the same level of feeling so powerless to effect any kind of change as I did at that time.

Greg E.: Yeah. No question the idea of your boss asking if you should hand out dildos as company swag, or having a VC partner you were working with offering up your female friend as a sort of conquest or offering to get somebody to work with your company. Those are eye openingly extreme examples of what, from the book, one could only gather you were dealing with on a pretty regular basis.

Jessica P.: Yes. It was a lot.

Greg E.: My editors at TechCrunch suggested I ask you about satire as a genre, which I see as an important part of ethics as a whole. You say in that same essay that satire “felt like the right approach for an industry that takes itself far too seriously and its own responsibility not seriously enough.” What would it mean to you if the kinds of high-ranking executives and leaders that you’ve worked with and around were to read this and laugh?

Jessica P.: We live in such a data-driven industry and culture in these tech companies, and that obviously can have a powerful role in painting a picture, but leads to black and white thinking that seems really prevalent in the Valley. Literature, not just literature, [and] the humanities generally, can connect to people in a different way. It encourages empathy, critical thinking.

But when I think about a lot of the books or the movies that come out about the tech industry, [they] paint people in a very one-sided way that makes it seem like all these CEOs are evil, or the tech workers are all just tech bros who are bad people trying to steal your data. If you’re working in these companies, as I once was, maybe you watch it for entertainment value, but I don’t think you consider that seriously. I wanted something that felt true.

If you’re working at a Google, or a Facebook, or plenty of other places, you definitely know the shoeless engineer. I wanted you to have moments that aren’t critical, just funny and part of your culture, part of the personalities and the people that you work with.

But as you’re reading this world that looks like yours, or it looks like an exaggerated version of your world, you start to understand a little bit more why the outside world is so scared of you. Because the problem with that whole data narrative, of, ‘we’re all just sitting there stealing everyone’s data,’ is if that was actually the case, if that was the end game, at least you’d know what the end game is, and then you could figure out what to do about it.

What really drives a lot of these companies is not [so] simple. It’s more this ceaseless expansion that actually knows no bounds. When you have a philosophy of ‘why can’t we do this?’ there is no stopping point, and I think that’s what frightens people. That where it’s headed isn’t clear. I wanted to capture that and have it not necessarily hit you right over the head the moment you open the book, the way I think some of these data privacy dystopiates do, but rather have it build, where you actually see why these companies expand. You can see how a company starts off saying, “Hey, we’re going to the moon.” And you think the moon is the end game, and then you actually discover the moon isn’t the end game, it’s actually a nation-state end game, it’s the whole world.

Greg E.: And this notion, that a tech company would want to expand to the moon and beyond, is not far off fiction. One would have to go through one’s list of all the different tech companies trying to get to the moon or Mars right now, to try to even figure out who you were satirizing.

Jessica P.: Right, right, right. That’s what fascinates me: how do you get from being a diaper store to buying Whole Foods? How do you get from doing search to self-driving cars?

Look at Google: you’re doing search, but someone can block people from getting to your search, like at Microsoft back in the day, so build a browser. You’re building a browser, but then you realize people can stop you at the hardware level, so build the hardware. Then you’ve got the hardware, but what happens if people don’t have the internet? You better build a cable, fiber.

Then with Facebook, how do you get from newsfeed to [solar-powered internet] planes? It’s this constantly expanding, watching other people, seeing what they’re building, they have AI, you’d better have AI. They have a drone, you’d better have a drone. When you’re in it, when you’re creating this stuff they feel like logical next steps.

Greg E.: And that thought process gets replicated in The Big Disruption — dramatically maybe, and certainly your fictional version of things is extremely funny, but I wouldn’t say it’s outlandish.

Jessica P.: [It’s,] you’re building this car, at first [as] a way for people to connect, and then it gets tweaked and it becomes a dating car. That becomes the way you get to the moon, because you want to get there to isolate all of your employees there. Then you [want to] create a nation-state [on the moon], and you just start creating more, and more.

Greg E.: All of this sounds a lot like actual Amazon, lately. Jeff Bezos recently told employees he’s “very excited” about the auto industry, which is the sort of sentiment that could easily launch Amazon into some sort of competition with Tesla, and meanwhile at a small recent invite-only event, Bezos described a future where there are space colonies with giant factories, trillions of people living on space stations, and all because the kind of “limitless growth” that made him the richest man on earth isn’t, as it turns out, actually all that compatible with humans sustainably surviving here on earth. You can’t make this stuff up.

Anyway, one of my greatest teachers, an atheist/secular humanist rabbi named Sherwin Wine to whom I dedicated a book, once explained that secular ethics needs to focus on the human condition, and we all know the human condition is absurd. “So people often ask me,” Wine said, “what’s your substitute for worshipping God? You worship people.” But Wine went on to say no — humanism and human-centered ethics is never, ever about worshiping people. “The alternative to worship,” he said, “has always been something I treasure; it’s laughter.”

This is what The Big Disruption really meant for me, in the end, and why I think what you are doing is so important. We are facing some truly absurd situations in our tech world today, and in life. Sometimes the best response to absurdity is to laugh at it.

In part two of my conversation with Jessica Powell, we discuss the meaning of “genius” in the tech world; why Silicon Valley multi-millionaires vote for socialists; and whether it is possible to use the master’s code to destroy his app.