Ben Roy explains why prompting an LLM to write an essay misunderstands what writing actually is:

People fundamentally can’t prompt good essays into existence because writing is not a top-down exercise of applying knowledge you have upfront and asking an LLM to create something. AI agents also can’t create good essays for the same reason. Even though their step-by-step reasoning is more complex and iterative than human prompting, a chain of thought is still trying to accomplish a predefined goal. By contrast, real writing is bottom up. You don’t know what you want to say in advance. It’s a process of discovery where you start with a set of half-baked ideas and work with them in non-linear ways to find out what you really think.

I will continue to argue that for general business writing LLMs are fantastic if they are given the right context and guidance, and that it can save hours of work (with high quality results). But all my experiments with using LLMs for creative writing has so far fallen flat. Maybe—likely?—that will change within the next few months. But for now, the brain work this kind of writing requires remains. Not a bad thing imo.

Tracy Durnell explores non-visual negative space—what happens when writing leaves room for the reader to think:

The current design trend of business and self-help style books is to use tons of subheadings and callout boxes and always, a list of the key points at the end of the chapter. While this is a highly skimmable format and often nice visual design, it essentially sucks the negative space out of the text — the places in which the reader might step back and consider their own examples or anticipate what point the author is trying to make. There’s no time for hunches here.

And:

The negative space of the text helps build the aesthetic experience. Small details flavor the text with a sense of reality. Drawing out events — leaving questions unresolved and conflicts unsettled — can build tension. And textual space creates a gap for the reader to make the personal decodings of the text that build meaning.

Not everything has to get to the point immediately. Sometimes the best thing a writer can do is leave room for the reader to get there on their own. I’m thinking about this because I’m currently reading The Will of the Many. It is slow, and long, and one of the best books I’ve read in ages. The negative space is probably a big reason why I love it so much.

Derek Thompson wrote a wonderful essay on what happens when you become a parent:

The baby you bring home from the hospital is not the baby you rock to sleep at two weeks, and the baby at three months is a complete stranger to both. In a phenomenological sense, parenting a newborn is not at all like parenting “a” singular newborn, but rather like parenting hundreds of babies, each one replacing the previous week’s child, yet retaining her basic facial structure. “Parenthood abruptly catapults us into a permanent relationship with a stranger,” Andrew Solomon wrote in Far From the Tree. Almost. Parenthood catapults us into a permanent relationship with strangers, plural to the extreme.

Paul Ford writes about vibe coding for the NYT (gift link) and what happens when software suddenly becomes cheap and fast to ship:

There are many arguments against vibe coding through A.I. It is an ecological disaster, with data centers consuming billions of gallons of water for cooling each year; it can generate bad, insecure code; it creates cookie-cutter apps instead of real, thoughtful solutions; the real value is in people, not software. All of these are true and valid. But I’ve been around too long. The web wasn’t “real” software until it was. Blogging wasn’t publishing. Big, serious companies weren’t going to migrate to the cloud, and then one day they did.

And then he brings it home in a way that continues to make him one of my favorite web writers:

The simple truth is that I am less valuable than I used to be. It stings to be made obsolete, but it’s fun to code on the train, too. And if this technology keeps improving, then everyone who tells me how hard it is to make a report, place an order, upgrade an app or update a record — they could get the software they deserve, too. That might be a good trade, long term.

We can grieve what we lost, while also being optimistic about the future AI is unlocking for all of us. It’s uncomfortable, but that’s ok, all technological shifts are.

A great list of things to keep in mind when communicating via writing. The article is focused on “managing up” but these principles are relevant in a much broader context as well.

What questions does your manager usually ask? Answer those questions yourself. If you take anything away from this article, make it this. Every manager has their own idiosyncrasies, worldview, values, etc. That’s why the best thing to do is to pattern match. Consider what they’ve asked you in the past, when talking to you or others. Try to give context through that lens.

Source: How I give the right amount of context (in any situation) →

This is a beautifully-written love letter to the CD—and I agree completely:

The commitment for the listener is light—one press of the button—and the challenge for the artist is pleasantly tough. You have to make all the songs work in a row, and there is a very good chance the listener will hear the entire album. One long unbroken work is also like a stage play, which is what I knew best in high school. […] The CD still delights me and helps me frame the idea of a collected set of songs.

Source: Requiem for a Beam →

Wait hold the phone. Frank Chimero is writing again! One of my all-time favorite design writers. Welcome back to my RSS feed, (Internet) friend.

I wanted to get back to walking, reading, and writing. These were the foundational practices during the most prolific and enjoyable parts of my career. I longed to feel generative again and to have ideas with depth, meaning, and pleasant uncertainty, ideas whose remit extended beyond the boundaries of one company. I missed the opportunities of the internet as a common place for finding your people and feeling like a part of a group that actually had ideas instead of opinions or pleas for attention.

Source: Time is On My Side →

This is fun research but did they have to use “reach out” in this quote.

According to a new study, using too much jargon in the workplace can hurt employees’ ability to process messages, leading them to experience negative feelings and making them feel less confident. In turn, they’re less likely to reach out and ask for or share information with their colleagues.

Source: Workplace jargon hurts employee morale, collaboration, study finds →

You know how those of us who read The Lord of the Rings before the movies came out got all weirdly and annoyingly upset about all the “new fans” and how they should have “read the books years ago”? That’s how I feel about the em dash and its AI takeover.

The real issue isn’t me—it’s you. You simply don’t read enough. If you did, you’d know I’ve been here for centuries. I’m in Austen. I’m in Baldwin. I’ve appeared in Pulitzer-winning prose, viral op-eds, and the final paragraphs of breakup emails that needed “a little more punch.” I am wielded by novelists, bloggers, essayists, and that one friend who types exclusively in lowercase but still demands emotional range.

Source: The Em Dash Responds to the AI Allegations →