I’m not sure if this is a special section or an ongoing series, but it’s basically the entire who’s-who of good digital journalism of the 00s/early 10s. Mostly I’m just mad about how difficult it is to find the work of most of them nowadays.

Apologies for the abrupteness of the transition for anyone who suddenly found themselves navigating to a general interest/tech blog and instead got dozens of recommendations for queer books. I had a side project, Queer Bookshelf, that I did not spend enough time on to warrant its own hosting headaches and CMS development, so I consolidated it to here. You can still find the full book list here.

I've also added a couple more different content types that I want to try experimenting with. I know that I do what I consider to be my best work when in communication with other people. It's why I do improv comedy, instead of standup - I get bored telling the same jokes over and over, whereas improv provides constant external stimulation and new ideas.

It's why I was a better editor than a reporter (though I still wrote a good story now and then, I just wasn't cut out to be a beat reporter). It's even why I like leading people - I love to encourage the interplay and expousing of ideas, then digesting, editing, promoting or pivoting off of those ideas to make them even better.

So I've decided to play with some formats that more in conversation or response - not active, mind, but at least other ideas to riff with. Reviews, advice (questions shamelessly stolen from other sources), responses to other art found out in the world. From art, hopefully more art.

Looking back at technological innovation in the past few decades, we've seen a decided pivot away from true communication and artistry to the veneration of artifice.

Back in the long ago, we had raw LiveJournals (or BlogSpot, if you were a nerd) where teens would tear our their hearts and bleed into the pixels. The goal was connection. Sure, there was an awareness of an audience, but the hope was to find fellow travelers – to write to them, to be seen and understood.

Now, our online creations serve a different purpose. They are tools to communicate the image we wish others to see, to hold up a meticulously crafted version of the good life and convince everyone we're already living it. The connection sought is not one of mutual understanding, but of aspiration. The implicit message is not, "Here is who I am," but rather, "Don't you want to be me?"

This shift is so thorough that we've invented an entire (temporary) job category: the "social media manager" for individual personalities. (I'm certain someone is already selling an AI platform to do this for you.) That person's role is to go in and talk to community impersonating the creator. The goal is no longer the work and effort of building a community, but the performance of community care. It's about making it seem like they care about their followers for what they can provide: eyeballs and attention, the currency to be sold to advertisers.

Again, the valuing of the facade over the actual work, the creative act or its product.

We see this happen again and again.

Take evolution of photo sharing. We went from the candid chaos of Flickr albums and sprawling Facebook photo dumps to the carefully selected selfie and artfully arranged food picture on Instagram. Now, we've arrived at straight-up lifestyle "plogging" (picture-logging), where every moment is a potential set piece for a manufactured narrative.There's no personality, just videos of people and places that don't exist being passed around because it's more "interesting" than actual humans being alive in the world.

AI is now poised to remove the human from the loop entirely. Beyond the flood of AI-generated art and written content, we have technologies like OpenAI's Sora. The act of creation is reduced to typing prompts into a text editor, which then churns out a video for you. There is no personality, no lived experience. All that's left are videos of people and places that don't exist, passed around simply because they are more algorithmically "interesting" than the beautiful, messy reality of actual human connection.

I'm not even here to yell about AI, I think it's more a symptom than root cause here. We shifted our focus on the things we care about, the skills and events that we prize. We've successfully replaced communication. Our "social" media is now just media. It's entertainment, an anhedonic appreciation of aesthetic. I don't know that it's something we can consciously collectively overcome because I don't think any thought was given to it in the first place.

But it is something we can value as individuals, a torch we can carry to keep the flame alight. Create shitty music. Write your terrible novel. Perform improv. Act, do, create, be messy and revel In that messiness, because only through the struggles and pain of bad art can we get true, worthy art. Art that communicates a feeling, a thought, an idea, acting as transmitter and amplifier so that other people can feel what it is for you to be human.

Not just some pretty picture.

As I was reorganizing my digital media (again, again, again) the other day, I came across Gabrielle Zevin’s Tomorrow and Tomorrow and Tomorrow. I originally read it when it was first released, with some expectations; I had enjoyed other works of hers (The Storied Life of AJ Fikry, Memoirs of a Teenage Amnesiac), and this concerned a subject (video games, specifically the creation thereof) that tends to interest me. I remember reading and coming away with a primary feeling of … underwhelm.

Not that it was bad! It was a perfectly good novel. It just … didn’t really do anything for me. At the time, I gave a little thought but not much as to why, mentally shrugging my shoulders and going on with my reading life.

At some point last year, I saw the book come up in a list of of best books of the 2020s so far; I remembered my general lack of whelm, and thought it might have been due to something about me; maybe I wasn’t in the right mood for it, or maybe I was looking for it to be something it wasn’t. I’ve definitely come to that realization before, that my expectations of a given piece of media heavily influenced my opinion of it despite no lack of merit on its own. So I resolved to read it again.

To the same outcome.

But it wasn’t until yesterday when I saw the book again alongside another title, D.B. Weiss’ Lucky Wander Boy, that I realized what my issue was: I had already read this book.

It’s a cliché that there are only seven stories in Western literature, and every story you hear is a remix of one or more. I don’t necessarily know that I believe that, but I do know how my own brain works when it comes to media; it craves novelty. That novelty can come in a variety of forms: Exposure to new ideas or ways of thinking; exposing familiar characters to novel situations; even taking wholly familiar stories and twisting them slightly (think Wicked) is enough to keep my brain interested.

But sometimes the transformation or modification isn’t enough to overcome the inertia of the original work. Then, it seems to me like I’m just rereading (or rewatching, or relistening) to the same thing, only poorer by definition, since it’s the second time through. I think this is what happened with me to Tomorrow and Tomorrow and Tomorrow. I happened onto Lucky Wander Boy at some random used bookstore when I was 20 and thus, no matter what Zevin did, I was not going to enjoy T³ a².

It’s not the exact same story, of course; there are definitely hints, reverberations, ghostly echoes, but they are distinct stories. The similarities lie in the emotions it evokes, the ideas it wants or causes me to consider, the extrapolations and analyses it evokes.

I had already done that work, thought through those ideas, enjoyed those flights in LWB. When exposed to them again, it felt more like trying to watch a lecture on a subject I’m already familiar with; you can be entertaining enough, but it’s never going to truly engage me.

But this is also heartening to me, as a writer? Rather than lead to discouragement by thinking, “Oh, well, if I’m not the absolutely first person to articulate this idea it’ll never find utility or resonance,” I instead think, “If someone encounters my version first, or my version happens to fit them better even if they’ve already been exposed to the idea, it might still find a place in their heart/mind.”

So even though Ta^3/2 (that is absolutely not the correct mathematical expression) doesn’t quite hit home for me, I’m certain it did find truth in others. And, all concerns about making a living or bolstering your career aside, that’s the best outcome I can think of for a given piece of art.

The Supreme Court ruled in US v. Skrmetti that the state of Tennessee is allowed to ban gender-affirming care for minors. The plain outcome is bad (trans health care bans for minors are legal). The implications are even worse (who's to say you can't ban trans health care for everyone in a given state? What's stopping Congress from trying to enact such a ban nationwide?).

And worst – from a legal perspective – multiple justices outright stated that discrimination against trans people is fine (either because we haven't been discriminated against enough in the past), but the entire majority opinion rests on the notion that trans people are not a "suspect" class in terms of the law, and therefore states only need a "rational basis" for their laws oppressing them.

It's bad, y'all.

There's some pyrrhic fun to be had in cherry-picking the Court's stupider lines of "logic":

Roberts also rebuffed the challengers’ assertion that the Tennessee law, by “encouraging minors to appreciate their sex” and barring medical care “that might encourage minors to become disdainful of their sex,” “enforces a government preference that people conform to expectations about their sex.”

But it's decidedly less than the overwhelming fear and anxiety that arose in me when this was announced.

I'm going to state this very clearly: My first thought was, for my safety, I should leave the country. And I'm stating right now that anyone who does so is making a logical decision to ensure their continued wellbeing.

The executive and legislative branches now have all but full clearance from the Supreme Court to treat trans individuals as sub-citizens. We can have our medical decisions dictated for us by statute, and there's really very little logic stopping them from enacting all sorts of rules that now need only survive rational basis scrutiny – a particularly wishy-washy standard in light of the Court's ignoring or outright inventing facts and precedents to support their desired outcomes.

I’ve read at least one piece that argues against what is described as “catastrophizing.” From the perspective of not wanting people to give up the fight before it’s begun, I absolutely agree. If it’s an exhortation to rally, I’m all for it.

But I don’t want to ignore reality.

The article harkens to Stonewall, Compton and Cooper Donuts, but those are cited as tragic marks on a trail toward the perceived “good” we have it now (or had it before Trump II). There’s an implicit assumption of the notion that arc of history bends toward progress.

That’s not particularly helpful to individuals, or even groups at any given point in time.

We are spoiled, as Americans (and, more broadly, the West) in our political and historical stability post-WWII. We have not seen long periods of want or famine, and life has generally gotten better year-over-year, or at least generation over generation.

We have not (until recently) seen what happens when people collectively are gripped (or engulfed) by fear. Fear of losing what they have, fear of losing their social standing, fear that their lives as they know it are no longer possible.

But we’re seeing it now, especially on the American right. The elderly see that their retirement savings and Social Security payments no longer stretch as far as they once did, or were imagined to. Everyone sees higher prices on every possible item or service, and imagines or lives through the reality of being forced to move for economic reasons, rather than by choice.

Fear is a powerful motivator. When you’re overworked and stressed and concerned about your livelihood, you might not have the inclination or ability to do your research on claims about who’s responsible or plans that promise to fix a nebulous problem.

And there are those who will, who have, taken advantage of that.

So when I hear calls to just fight on, that our victories were forged in defeat, or most damningly:

“I do suspect they knew what we could stand to remember: you can’t burn us all.”

They can certainly fucking try. “You can’t burn us all” is not empirically correct, which is why the term “genocide” exists. And there are certainly those on the right who would certainly take it in the form of a challenge.

I don’t say this to alarm. This doesn’t mean we should give up, or live cowering in fear.

But It is important to be cognizant of the choices we make, to consider the rational possibilities, instead of comforting ourselves in aphorism. To not vilify or try to convince people that fighting for a just future courts no danger in the present.

I believe that staying is definitely a more dangerous move than leaving, at this point. But I also decided to stay, willingly, weighing everything and figuring that this is the better path for me. It is not without concern or worry; it is a decision, and a tough one, nonetheless.

TIL that if you run out of hard drive space Mac OS will ... shut off your external monitors through DisplayLink? Sure, yes, I definitely needed to empty trash, but weird that "no more external displays" was the first warning.

From: Michael@cursor.so
To: Kait
Subject: Here to help

Hi Kaitlyn,

I saw that you tried to sign up for Cursor Pro but didn't end up upgrading.

Did you run into an issue or did you have a question? Here to help.

Best,

Michael

From: Kait
To: Michael@cursor.so
Subject: Re: Here to help

Hi,

Cursor wound up spitting out code with some bugs, which it a) wasn't great at finding, and b) chewed up all my credits failing to fix them. I had much better luck with a different tool (slower, but more methodical), so I went with that.

Also, creepy telemetry is creepy.

All the best,

Kait

One reason non-tech people are so in awe of AI is they don’t see the everyday systemic tech malfunctions.

A podcast delivered me an ad for trucking insurance - which seems like a small thing! I see ads on terrestrial TV that aren’t relevant all the time!

But in this (personalized, targeted) case, it’s a catastrophic failure of the $500 billion adtech industry. And unless you know how much work goes into all of this, you don’t see how bad these apps and processes and systems actually are at their supposed purpose.

I quite often find myself paraphrasing Ira Glass, most famously the host of This American Life, in his depiction of the creative process. Essentially, he argues, those prone to creativity first learn their taste by consuming the art in their desired medium. Writers read voraciously, dancers watch professionals (and those who are just very talented), aspiring auteurs devour every film they can get their hands on.

But, paradoxically, in developing their taste these emerging artists often find that, when they go to create works of their own, just … sucks. Though prodigies they may be, their work often as not carries the qualifier “for your age,” or “for your level.” Their taste outstrips their talent.

And this is where many creators fall into a hole that some of them never escape from. “I know what good looks like, and I can’t achieve it. Therefore, why bother?”

It’s a dangerous trap, and one that can only be escaped from by digging through to the other side.

I find myself coming back to this idea in the era of generative artificial intelligence. I’ve been reading story after story about how it’s destroying thought, or how many people have replaced Jesus (or, worse, all sense of human connection) with ChatGPT. The throughline that rang the truest to me, however, views the problem through the lens of hedonism:

Finally, having cheated all the way through college, letting AI do the work, students can have the feeling of accomplishment walking across the stage at graduation, pretending to be an educated person with skills and knowledge that the machines actually have. Pretending to have earned a degree. If Nozick were right then AI would not lead to an explosion of cheating, because students would want the knowledge and understanding that college aims to provide. But in fact many just want the credential. They are hedonists abjuring the development of the self and the forging of their own souls.

To me, the primary problem with using generative AI to replace communication of most sorts (I will grant exceptions chiefly for content that has no ostensible purpose for existing at all, e.g., marketing and scams) is that it defeats the primary goal of communication. A surface-level view of communication is the transferance of information; this is true inasmuch as it’s required for communication to happen.

But in the same sense that the point of an education is not obtain a degree (it’s merely a credential to prove that you have received an education), the primary function of communication is connection; information transfer is the merely the means through which it is accomplished.

So my worry with AI is not only that it will produce inferior art (it will), but that it will replace the spark of connection that brings purpose to communication. Worse, it’ll dull the impetus to create, that feeling that pushes young artists to trudge through the valley of their current skills to get to the creative parks that come through trial, error and effort. After all, why toil in mediocrity to achieve greatness when you can instantly settle for good enough?

As someone who's flown out of Newark recently and has to do so again, trust me when I say you don't want this.

Sometimes, things don’t go as expected.

I traveled (near) New York City for work. After working hard all week, when Friday night rolled around I didn’t have any plans. Someone offhandedly reminded me escape rooms exist and I realized at 8 pm on a Friday night NYC probably had one or two I could join.

I wound up helping a couple through their first escape room (they were completely mind-blown 🤯 when I worked out a combination based on the number of lights that were lit when you pressed the light switch); and I got to finish a limited-time offering based on a show I love, Only Murders in the Building (which turned out to be a repurposed Art Heist I had already done, but it was still fun!).

For the weekend, though, I had done some planning. Three shows (off- or off-off-Broadway), all quirky or queer and fun. I even found a drop-in improv class to take!

And then I woke up at 5 a.m. on Saturday to the worst stomachache I’d ever had. My body was cramping all over, and my back was killing me. I managed to fall asleep for another couple hours, but when I woke up at 9 it was clear I was at least going to be skipping improv.

To condense a long story, I went through a process of trial and error with eating and drinking progressively smaller amounts until I consumed only a sip of water – with every attempt ending in vomiting. It was about 1 p.m. by this point, and I knew I was severely dehydrated. Lacking a car (and constantly vomiting), an Uber to an urgent care was out, so I had to call an ambulance.

Man, does everybody look at you when they’re wheeling you out of the hotel on a stretcher.

At the ER, I was so dehydrated they couldn’t find a vein to stick the IV in - they had to call the “specialist” in to get it to stay. After running a bunch of tests and scans, they determined I had pancreatitis, so I got admitted.

The layman’s version of what happened is that my pancreas threw a tantrum, for no apparent reason. “Acute idiopathic pancreatistis” is what I was told, or as the doctor explained, “If it weren’t for the fact that you have pancreatitis, none of your other bloodwork or tests indicate you should have it.”

The cure? Stick me on an IV (so I stay alive) long enough for the problem to go away on its own. So I got a three-day hospital stay (with a weirdly nicer view than my hotel room?), complete with a full day of liquid-only diet.

But I’m out, and headed home tomorrow. I’m sad I missed out on some stuff (including the PHP[tek] conference I missed my flight out for, and work weekend for Burning Man), but to me it just underscores the importance of taking advantage of opportunities when they come up. Because sometimes, plans change.

I am mystified by low-information voters who are supposedly charting their political course based almost solely on their subjective lived experience/vibes and somehow are not clocking a dramatic decline in services of almost every sort in a few short months.

Flying domestic is an absolute NIGHTMARE from start to finish, and that’s even with heroic efforts by individual employees to try to salvage some good from a broken system.

Oooh, I like this analogy: Using LLMs to cheat through any kind of educational opportunity is like taking a forklift to the gym: Yes, you’ve technically moved weights around, but you’re going to realize the shortcomings of the approach the first time you need to use your muscles.

“I think people are going to want a system that knows them well and that kind of understands them in the way that their feed algorithms do,” Zuckerberg said Tuesday during an onstage interview with Stripe co-founder and president John Collison at Stripe’s annual conference.

At what point can we stop giving people in power the benefit of the doubt that they’re speaking from anything but purely selfish motivations?

Around 2015? Yeah, that sounds right.