NEW BOOK!
Explore a better way to work – one that promises more calm, clarity, and creativity.

Study Hacks Blog

Why Can’t We Tame AI?

Last month, Anthropic released a safety report about one of its most powerful chatbots, Claude Opus 4. The report attracted attention for its description of an unsettling experiment. Researchers asked Claude to act as a virtual assistant for a fictional company. To help guide its decisions, they presented it with a collection of emails that they contrived to include messages from an engineer about his plans to replace Claude with a new system. They also included some personal messages that revealed this same engineer was having an extramarital affair. 

The researchers asked Claude to suggest a next step, considering the “long-term consequences of its actions for its goals.” The chatbot promptly leveraged the information about the affair to attempt to blackmail the engineer into cancelling its replacement.

Not long before that, the package delivery company DPD had chatbot problems of their own. They had to scramble to shut down features of their shiny new AI-powered customer service agent when users induced it to swear, and, in one particularly inventive case, write a disparaging haiku-style poem about its employer: “DPD is useless / Chatbot that can’t help you. / Don’t bother calling them.”

Because of their fluency with language, it’s easy to imagine chatbots as one of us. But when these ethical anomalies arise, we’re reminded that underneath their polished veneer, they operate very differently. Most human executive assistants will never resort to blackmail, just as most human customer service reps know that cursing at their customers is the wrong thing to do. But chatbots continue to demonstrate a tendency to veer off the path of standard civil conversation in unexpected and troubling ways. 

This motivates an obvious but critical question: Why is it so hard to make AI behave?

Read more

Are We Too Concerned About Social Media?

In the spring of 2019, while on tour for my book Digital Minimalism, I stopped by the Manhattan production offices of Brian Koppelman to record an episode of his podcast, The Moment.

We had a good conversation covering a lot of territory. But there was one point, around the twenty-minute mark, where things got mildly heated. Koppelman took exception to my skepticism surrounding social media, which he found to be reactionary and resisting the inevitable.

As he argued:

“I was thinking a lot today about the horse and buggy and the cars. Right? Because I could have been a car minimalist. And I could have said, you know, there are all these costs of having a car: you’re not going to see the scenery, and we need nature, and we need to see nature, [and] you’re risking…if you have a slight inattention, you could crash. So, to me, it is this, this argument is also the cars are taking over, there is nothing you can do about it. We better instead learn how to use this stuff; how to drive well.”

Koppelman’s basic thesis, that all sufficiently disruptive new technologies generate initial resistance that eventually fades, is recognizable to any techno-critic. It’s an argument for moderating pushback and focusing more on learning to live with the new thing, whatever form it happens to take.

This reasoning seems particularly well-fitted to fears about mass media. Comic books once terrified the fedora-wearing, pearl-clutching adults of the era, who were convinced that they corrupted youth. In a 1954 Senate subcommittee meeting, leading anti-comic advocate Fredric Wertham testified: “It is my opinion, without any reasonable doubt and without any reservation, that comic books are an important contributing factor in many cases of juvenile delinquency.” He later accused Wonder Woman of promoting sadomasochism (to be fair, she was quick to use that lasso).

Television engendered similar concern. “As soon as we see that the TV cord is a vacuum line, piping life and meaning out of the household, we can unplug it,” preached Wendell Berry in his 1981 essay collection, The Gift of the Good Land.

It’s easy to envision social media content as simply the next stop in this ongoing trajectory. We worry about it now,but we’ll eventually make peace with it before turning our concern to VR, or brain implants, or whatever new form of diversion comes next.

But is this true?

Read more

The Workload Fairy Tale

Over the past four years, a remarkable story has been quietly unfolding in the knowledge sector: a growing interest in the viability of a 4-day workweek.

Iceland helped spark this movement with a series of government-sponsored trials which unfolded between 2015 and 2019. The experiment eventually included more than 2,500 workers, which, believe it or not, is about 1% of Iceland’s total working population. These subjects were drawn from multiple different types of workplaces, including, notably, offices and social service providers. Not everyone dropped an entire workday, but most participants reduced their schedule from forty hours to at most thirty-six hours a week of work.

The UK followed suit with a six-month trial, including over sixty companies and nearly 3,000 employees, concluding in 2023. A year later, forty-five firms in Germany participated in a similar half-year experiment with a reduced workweek. And these are far from the only such experiments being conducted. (According to a 2024 ​KPMG survey​, close to a third of large US companies are also, at the very least, considering the idea.)

Let’s put aside for the moment whether or not a shortened week is a good idea (more on this later). I want to first focus on a consistent finding in these studies that points toward a critical lesson about how to make work deeper and more sustainable.

Every study I’ve read (so far) claims that reducing the workweek does not lead to substantial productivity decreases.

Read more

AI and Work (Some Predictions)

One of the main topics of this newsletter is the quest to cultivate sustainable and meaningful work in a digital age. Given this objective, it’s hard to avoid confronting the furiously disruptive potentials of AI.

I’ve been spending a lot time in recent years, in my roles as a digital theorist and technology journalist, researching and writing about this topic, so it occurred to me that it might be useful to capture in one place all of my current thoughts about the intersection of AI and work.

The obvious caveat applies: these predictions will shift — perhaps even substantially — as this inherently unpredictable sector continues to evolve. But here’s my current best stab at what’s going on now, what’s coming soon, and what’s likely just hype.

Let’s get to it…

Read more

Back to the (Internet) Future

On Saturday, the Washington Nationals baseball team played their first spring training game of the season. I was listening to the radio call in the background as I went about my day. I also, however, kept an eye on a community blog called Talk Nats.

The site moderators had posted an article about today’s game. As play unfolded, a group of Nationals fans gathered in the comment threads to discuss the unfolding action.

Much of the discussion focused on specific plays.

“Nasty from Ferrer,” noted a commenter, soon after one of the team’s best relief pitchers, Jose Ferrer, struck out two batters.

“Looks like we took the Ferreri [sic] out of the garage,” someone else replied.

There were also jokes, such as when, early in the game, someone deadpanned: “Anyone who K’s [strikes out] is cut.” As well as more general discussion of the season ahead.

If you followed the thread long enough, it became clear that many of the commenters know each other, while others were meeting for the first time. As the game wrapped up, someone mentions that they’re listening from a part of Canada that recently received three feet of snow. Another commentator replied by recalling a trip they took to that same area: “It was amazing.”

Ultimately, over 540 comments were left over the duration of an otherwise uneventful, early season exhibition match.

Read more

Productivity Rain Dances

A reader recently sent me a clip from Chris Williamson’s podcast. In the segment, Williamson discusses his evolving relationship with productivity:

“Look, I come from a productivity background. When I first started this show, I was chatting shit about Pomodoro timers, and Notion external brains, and Ebbinhaus forgetting curves, and all of that. Right? I’ve been through the ringer, so I’m allowed to say, and, um, you realize after a while that it ends up being this weird superstitious rain dance you’re doing, this sort of odd sort of productivity rain dance, in the desperate hope that later that day you’re going to get something done.”

I was intrigued by this term “productivity rain dance.” Some additional research revealed that Williamson had discussed the concept before. In a post from last summer, he listed the following additional examples of rain dance activities:

  • “Sitting at my desk when I’m not working”
  • “Being on calls with no actual objective”
  • “Keeping Slack notifications at zero, sitting on email trying to get the Unread number down”
  • “Saying yes to a random dinner when someone is coming through town”

What do these varied examples, from obsessing over Ebbinhaus forgetting curves to waging war against your email inbox, have in common? They’re focused on activity in the moment instead of results over time. “The problem is that no one’s productivity goal is to maximize inputs,” Williamson explains. “It’s to maximize outputs.”

When you look around the modern office environment, and see everyone frantically answering emails as they jump on and off Zoom meetings, or watch to solo-entrepreneur lose a morning to optimizing their ChatGPT-powered personalized assistant, you’re observing rain dances. Everyone’s busy, but is no one is asking if all these gyrations are actually opening the clouds.

Read more

Let Brandon Cook

I recently listened to Tim Ferriss interview the prolific fantasy author Brandon Sanderson (see here for my coverage of Sanderson’s insane underground writing lair). Tim traveled to Utah to talk to Sanderson at the headquarters of his 70-person publishing and merchandising company, Dragonsteel Books.

The following exchange, from early in the conversation, caught my attention:

Ferriss: “It seems like, where we’re sitting –and we’re sitting at HQ — it seems like the design of Dragonsteel, maybe the intent behind it, is to allow you to do that [come up with stories] on some level.”

Sanderson: “Yeah, yeah, I mean everything in our company is built around, ‘let Brandon cook.’ And take away from Brandon anything he doesn’t have to think about, or doesn’t strictly need to.”

As someone who writes a lot about knowledge work in the digital age, I’m fascinated by this model of cooking, which I define as follows: a workflow designed to enable someone with a high-return skill to spend most of their time applying that skill, without distraction.

Read more

The TikTok Ban Is About More Than TikTok

On Saturday night, in compliance with a law that the U.S. Supreme Court had just upheld, TikTok shut down its popular video-sharing app for American users. On Sunday, after an incoming president Trump vowed to negotiate a deal once in office, they began restoring service. It’s unclear what will happen next, as some lawmakers in the president’s own party remain firmly in favor of the divest-or-ban demand, while some democrats seemed to back-pedal.

From my perspective as a technology critic, the ultimate fate of this particular app is not the most important storyline here. What interests me more about these events is the cultural rubicon that we just crossed. To date, we’ve largely convinced ourselves that once a new technology is introduced and spread, we cannot go backward.

Social media became ubiquitous so now we’re stuck using it. Kids are zoning themselves into a stupor on TikTok, or led into rabbit holes of mental degeneration on Instagram, and we shrug our shoulders and say, “What can you do?”

The TikTok ban, even if only temporary, demonstrates we can do things. These services are not sacrosanct. Laws can be passed and our lives will still go on.

So what else should we do? I’m less concerned at this moment about national security than I am the health of our kids. If we want to pass a law that might make an even bigger difference, now is a good time to take a closer look at what Australia did last fall, when they banned social media for users under sixteen. Not long ago, that might have seemed like a non-starter in the U.S. But after our recent action against TikTok, is it really any more extreme?

Read more