Writing About Humans in the Tech Age

A longform interview with journalist Lauren Smiley

Every year, I teach a writing workshop called “Narratives off the News.” Here is an excerpt from my syllabus:

A man jumps from a Manhattan skyscraper, a fire ravages a college dorm, a band of terrorists take over an elementary school. For each event, headlines around the world captured breaking news. But the stories did not end there. Many literary journalists find the most enduring stories by going back to the scene and interviewing sources months or even years after news broke. In this class you will learn to search newspapers, blogs, briefs, legal documents, social media and other sources for narrative story ideas. We will learn to go back after an event has become “old news,” keeping in mind that this approach can often lead to the most lasting profiles and narratives.

One prolific journalist whose work appears on this syllabus regularly is Lauren Smiley, a San Francisco-based features writer who unspools investigative yarns about humans in the tech age. She is a regular Wired contributor and has written for New York magazine and The Atlantic.

Five years ago, I remember teaching this particular course in-person before the Covid pandemic sent us all into lockdown. We were following unfolding news of a ship that had been quarantined in Tokyo. As a live exercise, I divided the class into four groups—each with an assignment to research the Diamond Princess and find a story.

In class, one group began tracking down names of passengers. Another began to research the overall history of quarantines on ships, dating back hundreds of years. Another looked into the mechanics, structures and labor divisions on cruises. The last group researched what scientists knew so far about Covid-19 and how it could spread in a confined environment. It was a narrative assignment on a deadline that turned up some fast and fascinating reporting.

I had no doubt at the time that at least one persistent reporter would eventually write up these events as a deep-dive magazine piece. Indeed, two months later GQ came out with “Inside the Nightmare Voyage of the Diamond Princess.” And in the same month, Smiley also published a memorable longform narrative in Wired: “27 Days in Tokyo Bay: What Happened on the Diamond Princess.” Both are examples of storytelling that take you into the twists and turns of this torturous journey. Both pieces were reported under tight deadlines (at least, tight for the magazine world).

I assign Smiley’s cruise ship piece as an example of a narrative in which a place is a main “character.” But I also often share her sharp writing at the intersection of technology and the human condition, for which she is so well known. Smiley has been called “one of the great chroniclers of technology’s impact on people’s lives,” by Longreads.

Lauren Smiley. Photo credit: Coleen Jose.

What I admire about her work is how, through her tech lens, Smiley unearths the wonder and mysteries of people—their choices, circumstances, flaws, motivations, passions, and quirks—traits that so often become driving forces within her narratives that illuminated these larger societal forces and powerful companies.

Smiley was also the investigative reporter for the "Broken Harts" podcast, and she was short-listed for the 2025 True Story Award for her Wired piece “Priscila, Queen of the Rideshare Mafia,” which is also a 2025 National Magazine Award finalist for profile writing.

In our chat, we talked about a few of her greatest hits, and about how to flesh out complex psychological aspects of a subject through reporting and interviewing. We also discussed write-arounds, finding ideas off the news, reporting challenges, editing tips, and why we still love this work.

Here is my interview with Smiley, which has been edited for clarity:

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I want to start with your latest piece, “Who Was Cyberbullying Kendra Licari’s Teen Daughter?” It is an incredible tale. Your pieces always have that surprise factor. Can you tell us a little bit about how this story—about a mom who was secretly bullying her daughter—came together?

This piece started as an assignment. My editor found a squib online when the mother had been charged. The stories talked about her catfishing her own daughter, and mentioned that the term “cyber Munchausen by proxy” was being floated by the prosecutor. But the articles were “just-the-facts” news stories.

That’s interesting. In classes we talk about how often these longform pieces start as small stories that maybe ended up as a small nugget somewhere.

Exactly, you could tell this news story had a whole world inside of it. There was no assurance going in that I was going to be able to talk to the family at the center of the case, but it looked like the mother had interacted with both the school officials and law enforcement, and led them on a wild goose chase to find the culprit. I thought that if nothing else, maybe they’d speak with me.

Once I got the police report, I found out that two other families were very much drawn into this. The family of the daughter’s ex-boyfriend – it turned out he was also getting the bullying texts, and his family was in the trenches of this turmoil, too. And Kendra Licari framed another girl at the high school, and her family became very involved to get to the bottom of it. I got in contact quickly with those two families, and they seemed like they were onboard to speak in-depth about what they’d been through with this saga.

My hope was always that we were also going to be able to speak with the family at the center of the case. That part never worked out.

So you start with this idea, and then you begin to understand there are other people involved you can talk to. At that point are you thinking of twists and turns already within a story?

One key thing was that the criminal investigation went on for a year, which tells you the story is going to develop over time. That’s more interesting than, say, a couple texts that led back to a bully within a week. Because everyone had to go through a real journey with this.

After some phone calls with the other families involved, it was time to go report in person. I coincided my reporting trip to Michigan with the sentencing for Kendra. I think I stayed for about eight days in town, and that’s a big tip I have – to stay just as long as you can, especially if you’re not going to be able to go back. You’ll meet more people once you’re there, and it helps to be able to return a few times to talk with your sources. Also, sometimes things fall through and you need to reschedule.

There are things you get by showing up. Of course, by phone, you can get a lot, but there's something different about face-to-face.

I could not have done this story without going there. You’re introducing readers to new people and to the world of the story. You have to meet the main people, ideally at their home, because it quite literally shows you where they’re coming from. I asked to see the teens’ rooms, because that shows so much about a kid’s personality. I take a million pictures, because information comes at you like a firehose when you’re on reporting trips and you need to be able to look back. By being there, I also understood just how confounding it must have been to have the cyberbully get away with this for so long when I saw how tight-knit the school was.

So, the main family at the center of this story wouldn't talk. How do you get around that?

Well, we tried many times, let time pass, and tried again. I first reached out to the mother’s attorney, asking him to give Kendra a note for me. I emailed and mailed snail-mail letters to other family members. I ended up speaking with a relative who was helping them through this crisis in their family. She also helped pass along some messages for me. Soon enough, I learned that there were two competing documentaries following this story. When I finally was able to have a very short conversation with the father, he said he was talking to the documentary already, and wouldn’t speak with me. The mother wrote me from jail, but ended up not following through with a promised in-person interview. I would have greatly preferred to tell this from everyone’s perspective, but I had to work with the reality before me.

Do you have any tips on doing a write-around?

Well, it helped that there were two other families, a community, a school, and law enforcement–we’re talking a lot of people here–that had been drawn into this guessing game of what in the world was going on. All of these people were quite consistent in their memories.

My editors and I really debated when to reveal that the bully was the mother. In the end, we opted for the approach of letting dramatic irony drive the story. The audience knows more than the people in the story.

Yes, we are thinking: How did this happen? How did they get here? We know the mom is the bully, but what on earth, how and why?

Otherwise, it's a typical cyberbully story, with parents worried about who is cyberbullying their children. It’s more interesting to watch someone weave this web.

That's a really good piece of writing advice too. If you are building the whole story around “who is the cyberbully,” you could lose the reader. They might feel like they’ve heard this story before. But if the readers know the mom is the secret cyberbully, but everybody else in the story doesn't know, the dramatic irony propels the narrative.

Then there was a huge public records aspect to this story. This happened in a public school. So, I was able to do a public records request for all emails that mentioned the cyberbullying case. So helpful: people do not remember dates. Details dull with time. They just remember this swarm of madness around this case, so the emails put actual dates on specific aspects of this investigation. It also surfaced emails from the mother, which I could quote. She had also worked for two public universities, and her deceit to everyone about her jobs was another important aspect of this case. I was able to piece together what actually happened by doing a request for employment records.

How long did it take to get all the records?

The school records arrived quickly. The full sheriff’s report took a bit longer because someone had to redact the hundreds of pages. People may not understand that feature stories like this one are still supported by a huge stack of records.

You have these themes throughout your work, and a lot of times we're brought to our story ideas because we're just inherently interested in certain themes. I always tell students: “You already have an eye for stories. In what you pay attention to. Your life experiences draw you to notice certain ideas.” What is it that's drawing you to certain themes and stories?

I would say a lot of this comes out of just my particular biography. My first journalism job was at an alt-weekly here in San Francisco in 2007. The sensibility was narratives with a beginning, middle and end. They loved counterintuitive twists. They didn’t want a story that you could already imagine where it’s going when you hear the topic. And I would also say Jon Franklin's Writing for Story had an outsized impact on how I started looking for ideas.

Franklin talks a lot about picking the right story, how to pick the right character. And it's often the person that has agency in the situation – making decisions, navigating through life. That can be a very active thing, you know, like Kendra Licari perpetrating this mystery upon this small town. But I also think, for example, when our friend Jaeah Lee writes about the mother of a man who was killed by the police in San Francisco, she also shows there's agency there too, in how she moves through her grief. So, it can be the loud type of agency or a quieter, more subtle type of agency. They both work.

Franklin’s big example is a story about a surgery, “Mrs. Kelly's Monster.” He talked about why, for him, it was much more interesting to profile the surgeon than the person getting a brain surgery, because the surgeon is the one who actually has more to say in this situation. He's moving the plot forward.

As far as writing about tech-ish topics, I live in San Francisco, and this tech boom came and ate our city in 2012. I took my narrative story sensibility and brought it into this tech sphere. I'm never going to be the one who’s that interested in telling you about the latest gadget. I like narratives of people navigating through the world, and I’ve just applied that story sensibility to this particular topic area.

Did you go to journalism school?

I did, but I would say this is a job where you really don’t have to. The learning is in the doing. Still, I wrote for my high school newspaper. And then I went to the University of Iowa, and I wrote for The Daily Iowan, mostly feature stories. I did internships throughout college at feature desks of regional newspapers. I didn't quite know how one gets to a magazine. Iowa’s program was strong but pretty newspaper-centric at the time.

Then I got ahold of those Best American Magazine Writing books that came out each year. They blew my mind. Suddenly I was like: “Whoa, there's this whole other art form out there.”

How then did you decide to do freelance pieces?

It's so sad that alt-weeklies, which were a kind of onramp to magazine journalism, have largely dried up, because that was an amazing longform training ground. I spent five years at one, and it was a brutal learning curve, but I'd kind of finally reached the point I could do it and felt like I could pitch elsewhere.

The first landing pad as a freelancer was at what was, at the time, the re-energized San Francisco magazine. The fantastic story editor Nina Martin, now at the Center for Investigative Reporting, was a hands-on mentor to me, pushing me to up my writing game. She really held my hand at an important juncture.

I dipped in to work for Matter, this ambitious longform outlet that was run by a tech platform here in San Francisco called Medium at the time. Those 14 months changed me into a tech-ish reporter. Then as a freelancer I started pitching Wired and writing for them very consistently.

Can you talk about reporting “27 Days in Tokyo Bay: What Happened on the Diamond Princess?” This narrative on a deadline, reported in the early days of when the world was shutting down, and no one knew what would happen with Covid.

Snapchat and Tiktok, I relied on both of them at first, because the cruise workers at that point were in quarantine in Tokyo, trapped in dorm rooms. A lot of them were young Filipino workers, and they were entertaining themselves by singing on TikTok. They were tagging them #DiamondPrincess, I think, which made it easier to search. Once I found one, the platform started suggesting all of them to me. I started DMing them. Also, the Indian workers had made their way back to India, also stuck in a two-week quarantine.

Those were the shaky early days of a longform story. You don't know if anyone's going to talk to you, or if they stick with you after a 15-minute conversation. I think when I was just starting longform, I had this sense that veteran writers go into a story already knowing it's going to work, and the sources immediately divulge their life story the minute they pick up the phone, in a chronological fashion. Not so.

You talked earlier about the importance of showing up, but what did you learn about virtual reporting? How to reconstruct a narrative from afar?

Ask for as many scene details as you can. Also, people take so many cell-phone pictures and videos now, so ask for those. One cruise passenger had audio-recorded all of the on-board captain announcements. One had taken a picture of the ship’s instructions to the crew. You can build your description of the boat from official pictures on the cruise company’s website, plus news photos and social media.

Then it helps to talk to people multiple times. I focused on a cruise worker who was very consistent about picking up his phone. He felt the debacle had been handled inhumanely, so he was propelled by a sense of injustice, and he also had time because he was sitting in quarantine. For passengers, I homed in on a doctor from Tennessee and a guy from Sacramento who’d been doing a lot of tweeting from the ship. I spoke with the ship captain.

Then I just started building a huge chronology, which I do for almost every story. I put details from news stories and my interviews together in a long outline with links to the original source. You can start to see how this event evolved over a two-week disaster.

You have a great lede for your story: “Priscila, Queen of the Rideshare Mafia”:

“To understand Priscila Barbosa—the pluck, the ambition, the sheer balls—we should start at the airport. We should start at the precise moment on April 24, 2018, when she concluded, I’m fucked.”

Priscila was complex. How did that story even come together? How did you get access, and connect with her to flesh out her personality?

I loved working on this story. It started with a press release I found about the indictment of 19 Brazilian nationals who had been busted for this ring of creating fake accounts in the gig economy. I was on the U.S. Attorney's website, trawling through their press releases, looking for a story.

I've covered the gig economy through the years. News stories about fake accounts were out there, but I wanted to know what the enterprise looked like up-close. How did the ring members bypass the system? How did they think about what they're doing? What does the day-to-day look like?

I started by writing a volley of snail-mail letters to the inmates. In the federal system, inmates are often held in county jails until sentencing, and it is usually not obvious in the court docket where. I had to call around to jails in the Boston area and ask some helpful people: “Where do the feds typically hold inmates prior to sentencing?” They gave me some institution names, and after more hunting and calling, I finally found about a dozen of the defendants and wrote them letters.

And Priscila was hands-down the person I most hoped to hear from. She was one of two women. She was one of the most prolific, and in fact, was the one that had allegedly made the most money. She was the one person who called me back.

Sometimes it's just meant to be.

My interest there, beyond the intriguing tale of how an ordinary person outwitted Silicon Valley platforms to create a shadow gig economy, is that Priscila is both an immigrant and a woman—two groups that often are cast as either a villain or victim. Especially immigrants right now, there's such a shrill casting of people that just doesn't account for the complexity of the human experience.

When you read it you get to understand and know Priscila. Even though she's doing all this sketchy stuff, there's something very likable.

When we started pen-palling from prison, I had no idea what she was going to be like as a person. And she said something in one of the early emails—she wrote about coming to the U.S., how she showed up to JFK Airport, and she only had $117. With no car, she had to walk from her apartment to this pizzeria, her first job. But then she wrote something like: For the first time in my life, I finally had a perfect body. And I'm like: “Whoa.” She's a modern, relatable lady.

It’s a gift when a source is willing to share their full selves - warts and all – in interviews. Also tonally, it would be a huge mistake to write that story in an overly serious way. When you have a character like this, you've got to match their personality in your tone.

These are the kind of people that are the most interesting and fun to write about, and people connect with them. We see them in all the human dimensions. Not just a hero or a villain. It's somebody who is contradictory, funny and flawed, which is how people are.

I really try, just on a technique level, to weave in aspects that are not the angelic parts of their personality, but in a way that just makes them seem more human, more like the reader, like me. Most people did not react to that story out of anti-immigration political viewpoints.

Did you worry about trolls?

It was running in the months up to the election. We did not know what was going to happen with this. I thought: We can just tell the best story we can. And it's true. For the most part, people just responded to her as a personality and as a person. People also found the tale itself compelling. It was a nearly 9,000-word story, and we were able to keep it moving.

Structurally, what was the thinking around that? How do you keep a 9,000-word story moving?

I always knew I wanted to start at the moment she lands at JFK with $117, because I had been thinking that through myself so many times. Like, what would I do if I only had enough money for one night in the most terrible hotel in New York City?

And she sold a ring to get the plane ticket.

Exactly. No backup. There's no hidden savings account somewhere. You just have to start moving in this new country with $117. The person who was supposed to be her person that ferries her to Boston and helps her get settled completely stood her up. So, I started with that moment, and just showed in so many ways, every point of her story was just the next pragmatic decision for the circumstances ahead of her.

Structure-wise, it was just ticking through the big moments when things change. By the end of the second section, she’s renting a Lyft account from a middleman. By the end of the third, she has made her own fake account, in business for herself. By the end of the next section, she's starting to build this into an empire. It ran at about 8,700 words. I think I turned in like 10,500. People think that when you write longform, you love to hear yourself write. In fact, I’m very open to cuts, because no one's going to spend this amount of time with your story if it's not just utterly compelling. With a first draft, I want my editor to see what’s there there, to know what we're dealing with. And then we can start cutting, once we both know the story.

It's almost like anticipating all the questions the editors are going to have. They know you have it, and then you're refining, refining, refining.

Yes. Nina Martin, actually, when we were at San Francisco Magazine, told me: “I'd rather see what you have than wonder what I'm missing.”

I do find that great editors do not mind very long, shaggy drafts. They're kind of okay with it, because they do want to see what you have, and they'd like to shape it with you.

That is a process itself. It's almost like you have to get it all out and then sharpen it.

Totally. I took a writing workshop with Daniel Duane—and he teaches the “read your sentences out loud” method. It is so annoying to do, but it surfaces so many issues quickly. Like this sentence is just too long. Or this is a hiccup word. Or this is just really clumsy. We got the Priscila story to read faster by getting these little road bumps out of the sentences.

You always get into the psychology of people, which I also love to do. How did they become this person, at this crossroads, or facing this challenge in their own particular way? You do this also in “Collision Course,” a story about a family that staged car wrecks, injured and bloodied themselves to pocket $6 million. Can you talk about how you dig into human motivations and behavior?

Coming into that story, I was very worried it was just going to be so grisly and dark that it would be hard for readers to care about these people.

I started reaching out to people with prison letters. Once I got on the phone with, for example, the daughter, I was just thinking: You know, these people just seem kind of normal. They've just been in this very dysfunctional family. Without having this dad, none of these people would have ever done this. The big question to answer is: “How in the world does one get to the point where you would cut yourself or break your own tooth?” To me that is so unfathomable, right? There was a big bridge to cross here to make this in any way understandable.

You have these people you're trying to understand. As a reader, we're trying to also put ourselves in their shoes. Would I do the same if I was in that position? Maybe it's not such a thin line. It seems crazy to hurt yourself, but you're explaining the forces beyond their decisions. It is so important to humanize.

I read Adrian Nicole LeBlanc’s Random Family back in the day. To me, that's just the bible on non-exotifying people that are involved in a crime. That was a remarkable work of reporting. I read this maybe 20 years ago now, but I still remember this one detail about the laundromat soap:

Boy George also demanded color coordination. “He matched me up,” Jessica said. No white clothes in winter, nothing stained or borrowed, no jeans with the yellow sheen from the cheap soap at the Laundromat, no vinyl belts sewn to the waist of the pants. He drove Jessica to Greenwich Village and introduced her to the $50 rule. Nothing under $50 was to be taken off the rack. No $10 stores, no V.I.M., no Jimmy Jazz, no Payless. He was generous with his money. After he bought her things, he didn’t demand sex. (Page 52)

The cheaper soap had a certain sheen. A slight status detail. I just thought: That is such an insane anthropological detail that one would ever know about.

I mean, my story was in a very different social milieu than Random Family. But that passage shows how close a nonfiction writer can get to inhabiting someone’s perspective.

It makes me think of Tom Wolfe’s status details. But the anthropological level Adrian included was even beyond status. It was human understanding, human decision making. It tells you so much about how somebody lives their life differently and why. So, it feels like these are the kind of elements that you're aiming for. But then how do you get that? Are you always thinking about that in your interviews? I think of them as intersection points—these sort of moments of connection of humanity. These moments when you think: I'm so different from this person, but I get it.

A lot of it is just being quiet. Especially during early interviews, I tend not to talk a ton until there's a need for a question. I just let people go – as long as it seems somewhat relevant – and that is the beauty of having time. That is also the beauty of this longform journalism we do as freelancers. Very few publications pay for you to spend this much time with people.

Another question I had about “Collision Course” is in reference to using the second person in your intro, and why you made that choice. Here is the opening:

Mize hurt you one at a time, pulling tools from a briefcase, cold and businesslike. He’d gash your brow with a razor or box cutter. Scuff up the wound with sandpaper, gripe if you didn’t bleed enough. For concussions or a busted knee, he’d smack you with a liquor bottle, a brick, a frying pan. You’d chug a Red Bull to spike your blood pressure. Pop aspirin so your blood would stream faster. Spill a bottle of your urine on your pants like you’d blacked out.

It was, again, about trying to cut through that sense of exotification of these people and what they're doing. Trying to get you mainlined into their world immediately.

It's a little TV-like, too – as storytellers, you’re allowed to take inspiration from all forms of storytelling. I think the opening monologue of “House of Cards” is pretty brilliant writing, where Frank Underwood breaks the fourth wall to talk to you about how DC works. There was a similar vibe here. Let's just get really quickly into the character’s mentality.

Here is a big-picture question: You are somebody who loves longform. You do this work. It's hard work. You've been through all the ups and downs of it. You’re a freelancer, which comes with its own challenges. Why do you believe in this work? What is the value that we're providing with our work?

I feel there's few other professions in which truth is the goal. The ability to get in there and find out the truth of what people are thinking and what's driving people to do the things they do, and be able to just state that, and show people's lives—this is a rare profession and sort of revolutionary. It's hard to get people to tell you their stories to this degree. All of us who have done these stories about delicate subjects know it is not a linear path. People go in and out of contact with you. They have a lot of feelings about talking with you, which you navigate during long reporting processes. It takes a lot of patience, a lot of time, and I sometimes think that half the job is worrying if the story will work out.

Despite all that, there are still moments where I look away from my desk and think: I'm very excited to do this work. I love this profession. It’s such an interesting way to live.

For me there are different levels of it. There is finding the idea and knowing that it hasn't been told in this way, or just bearing witness to the human experience, for me, always feels like a privilege. You just don't get to talk to people or strangers like this in everyday life. Then there's the structural part, which is kind of the hardest for me, but also a puzzle, a challenge. I'm wondering for you, what are the parts that excite you, and keep you motivated?

The bearing witness. The being able to tell these people’s stories that otherwise just would not be told, or that people in power don’t really want told. I’m sure no gig economy company wanted me to write that story about Priscila, or about Jeffrey Fang, the DoorDash worker whose children were taken when his van was carjacked. We gave him as many words as we would give a CEO profile. I find him as interesting as any CEO.

It's the buried treasure aspect of it. It takes work to find the right stories.

When I read good, longform journalism, when writers are so in control of their technique, and the way they're telling this story, that still kind of startles me. Oh, this is what this form is about. This is what you can actually do in journalism. I'm still a big fangirl of a lot of writers.

Which writers do you admire?

When I discovered the Best Magazine Writing book series in college, and I read Michael Paterniti’s “The Most Dangerous Beauty,” this story really broke my mind at the time. His control over his technique, his beautiful use of language. I think I read it when I was about 19 and I literally cried, because I didn't know journalism could be like that.

I am also very much a big Liz Weil fan. I've gone to her workshops here in San Francisco, and she talks endlessly about elevating your material beyond just a string of facts, even very interesting facts. She wrote a story about a long-distance kayaker. I didn't expect to like that story. I'm not really into adventure sports. But she makes it something you are interested in. She makes it speak to something essential, that the root cause of why he's doing this is to prove he's alive. I do still love it, this torturous art form that we do.