A few weeks ago, I met an acquaintance for coffee at a Cuban café attached to a downtown hostel, where people with backpacks of varying dimensions passed steadily through the lobby. He worked at a nearby university and had messaged me on LinkedIn saying he wanted to tell me about the campus and talk about teaching some night classes. Knowing academia and the speed at which it tends to move, I interpreted “talk about teaching” as something closer to perhaps someday, pending several committees and a minor geological event.

I ordered a large black iced coffee in a clear plastic cup with a black straw. After sitting for a few minutes, he asked if we wanted to turn this into a walking meeting. 

Somewhere between being handed a peel-and-stick visitor badge by a friendly security guard and being introduced to the dean with, “This is Ashlie, who I told you about,” I realized our casual coffee had become considerably more interview-shaped than I had anticipated.

I, meanwhile, was carrying a sweating plastic cup.

Thankfully, I had taken an extra napkin from the café. After being shuttled in less than half an hour between aggressive air conditioning, a muggy Chicago street and the temperate library, the cup had begun producing condensation at an alarming rate. I swaddled it in paper and successfully completed my introductions with a non-moist handshake.

All this to say, I understand why the question of whether iced coffee is unprofessional has taken over my feeds for the last several days.

By the time I reached the argument on Sunday — while scanning my phone on the train, heading, truly, to get another iced coffee — the original TikTok from a corporate recruiter warning that bringing one to an interview looked overly casual had migrated to LinkedIn. There, the discussion shifted from seven-part heroes’ journeys centered on skipping little luxuries like Starbucks to drink-based dominance theory. One piece of advice I encountered warned against accepting any beverage during an interview because doing so made you “the beta.”

I scoffed.

Soon, however, I started mentally moving my own cup through different rooms. Coffee-shop meeting: obviously fine. Conference table: Less so? Hot coffee: more professional somehow? Dunkin’, in one of its decidedly undemure pink-and-orange vessels? A tasteful local cup, perhaps communicating discernment and neighborhood loyalty?

Admittedly, my professional history makes me a poor control group. I have spent most of my career in newsrooms and restaurants; one restaurant poured me an iced coffee before we sat at the bar to discuss a front-of-house job.

Still, I eventually found the fear. My brain furnished the room immediately: C-suite office. Pristine mahogany desk. No coaster. One sweating plastic cup inching toward permanent damage.

The more I thought about the coffee, the less the coffee seemed to be the point. Professional life is crowded with micro-signals — clothes, cups, phones, tone, timing, posture — ordinary things that remain perfectly neutral until someone decides they are evidence of character.

Maybe this is why I have long treated “Ask a Manager” as both advice column and anthropological expedition behind the cubicle wall, where completely ordinary behaviors can become freighted with professional meaning. In one personally beloved 2015 post, readers confessed to cheerfully disappearing for two-hour lunches because the company had advertised Spanish classes, heading off to yoga in the middle of the afternoon because, well, yoga was offered, showing up to a board meeting in jeans and a hoodie, and maintaining what amounted to a full-service beauty counter in a cubicle, complete with makeup brushes and a plugged-in hair straightener.

Some of these people were not flagrantly blowing off work. They were trying, quite earnestly, to understand it. You said the company values work-life balance; I am therefore going to yoga. There is something almost touching about the literalism.

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The problem with unwritten rules, of course, is that some people have already been taught them.

A friend of mine once received paternal advice to retire his collection of personality socks until he had secured a job at a law firm. These were not, I should stress, shocking socks. They were J.Crew socks: tiny lobsters, reindeer, tasteful little acts of rebellion occurring mostly below the trouser cuff.

This is the maddening bargain at the center of so much professional advice: show personality, but not too much. Be memorable, but not for the wrong thing. Be yourself, but preferably the version of yourself who already knows how much of yourself this particular room permits.

“You don’t want to give them a reason to say no,” his father told him, “especially a dumb one.”

That wisdom becomes less funny the farther you stand from whatever a workplace has already decided looks like belonging. If you fall outside the traditional corporate default — by class, race, gender, disability, accent, education or simple familiarity with white-collar culture — more of those supposedly intuitive rules may have to be learned in real time.

And then there are people with enough status to become their own code. I once had a news director who, in the midst of marital issues, carried a guitar from cubicle to cubicle like the world’s saddest bard. Some found it charming, some unbearable, but in the end everyone shrugged: Well, he’s the boss.

Then the pandemic arrived and made the whole system stranger.

For a brief period, Americans thought very hard about what was behind their heads. A bookshelf became a statement. So did a plant. Room Rater built an audience scoring Zoom backgrounds for lighting, depth, art and visible cords; books themselves became set dressing.

This now feels faintly incredible. We were all amateur production designers of our own domestic lives.

And yet something did change. A dog wandering through frame became normal. So did a kitchen. A child interrupting a meeting became, depending on the meeting, either completely understandable or still mortifying. The rules did not disappear; they became even more dependent on that maddening instruction: read the room.

Which may be why we keep turning tiny behaviors into evidence of enormous generational shifts. Take the “Gen Z stare,” that supposedly blank look younger service workers give customers expecting a burst of social acknowledgment. I’m less concerned with whether a cashier performs delight at my arrival than with the more substantive question of whether younger workers had fewer chances to practice things like communication, adaptability and conflict resolution during a digital-first, pandemic-disrupted adolescence. Employers have reported concerns in precisely those areas, though those skills can also be taught and practiced.

There are rituals of professionalism whose disappearance I will survive. I do not require the personality socks to remain hidden. I do not need a service worker to beam. I do not believe hot coffee carries an innate moral seriousness unavailable to iced.

What I do think we owe one another is basic situational awareness.

There is an old Yiddish joke: the schlemiel spills the soup; the schlimazel is the person it lands on. My professional philosophy may amount to little more than avoiding becoming the iced-coffee schlemiel.

There is also an evergreen iced-coffee joke online: the person who arrives late blaming the train, fresh coffee still in hand. That, frankly, bothers me more than almost anything else raised in these etiquette debates. The coffee isn’t the problem. The suspiciously fresh coffee accompanying your late arrival might be.

Don’t put the sweating cup on somebody’s papers. Don’t make your convenience someone else’s inconvenience.

Bring the iced coffee. Just don’t be late because of it.

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Digital journalism is as subject to fads as any other medium. Snarky fisking — responding to an article line-by-line — gave way to the quiz boom, which was consumed by the personal essay before the long decade of short-form video. But if you squint, you can see the outline of the type of stuff that always works. 

Gossipy reported pieces on scams and relationships, such as the latest news about Donald Trump’s aide Natalie Harp or The Cut’s regular output, are always a safe bet. Fightstarters over ambiguous issues — the annual argument over “Baby, It’s Cold Outside,” the internet-breaking Dress, countless poorly written math equations on Facebook — are evergreen. Barring that, it never hurts to channel Helen Lovejoy from “The Simpsons”: You won’t go broke thinking about how we should all think of the children. 

Over the weekend, one such piece tore through the well-meaning liberal corners of the internet — meaning Bluesky and Threads, mostly — and prodded at the gap between educational idealism and the hyper-competitive reality of schooling in America. 

In a column for the New York Times Magazine titled “In Fighting for Every Black Child, Did I Betray My Own?”, Nikole Hannah-Jones agonizes over her decision to walk the walk with regard to her belief in robust, well-funded public schools for all children. The journalist made the decision to send her child to a Brooklyn public school whose student body was predominantly Black and impoverished, believing that her well-resourced family could help push for better education for all the city’s children from within. She wrestled with the struggles her daughter faced while trying to get ahead and deciding to test into one of New York’s ultra-selective specialized public high schools.

In her column, Hannah-Jones grapples with the ways underfunded schools leave even talented students feeling pre-emptively defeated — a sense that the city’s elite schools are beyond their grasp, even if their own test scores might indicate otherwise. Overworked and burnt-out staff teaching the children of overworked and burnt-out adults isn’t a recipe for educational success, and Hannah-Jones’ recollection of her repeated frustrations and conversations with educators paints a heartbreaking picture of a systemic issue that no one family could reverse. She makes herself sick with guilt over her choices, reaching out to activists and her daughter’s former educators to help her make sense of the problem and her response to it. 

But Hannah-Jones is ultimately unsuccessful. As the principal of her daughter’s struggling middle school puts it, “there’s no model out there for holding all of these truths, these complex truths, all at once.

“We are working within the system that we know is not working, while trying to recreate and reimagine a new system, while working with young people who have all this potential, who’ve not been given the opportunities for that potential to thrive and be unleashed,” the educator says.

In the end, Hannah-Jones’ daughter succeeded against the odds, landing in a great test-in school. But it’s hard to come away from her story believing that such a result would be attainable for others. 

Once the column hit the web, it quickly devolved into a fight over whether wanting the best for your child is a betrayal of egalitarian ideals. Hannah-Jones is a gifted writer, and her piece isn’t as flat as that argument implies. But the dilemma pokes at what has long been a sore spot for well-heeled liberals. Are the exceptions that every parent would make for their child morally permissible? Does sending your child to the best possible schools make believers in a better world for all big, fat hypocrites? 

I’ll let you in on another bit of digital journalism that always holds true: Questions explored in commentaries are either unanswerable or the answer is “no.” We should have well-funded schools for all American children, where success isn’t so tied to where you call home and the relative affluence of your neighbors. We don’t, though and kids only get one shot at raising their children.

Like Hannah-Jones and her husband, I was the product of well-funded public schools. Private school was never an option for my working-class parents, but living close to the vacation homes of wealthy people boosted the quality of public schooling. The coastal county where I was raised is even wealthier and more populous now, but Florida’s rightward turn to school choice, along with a post-COVID crackdown on classroom curriculums that might be deemed “woke,” has left those same public schools poorer and its teachers less free to do their jobs. The state is currently in the midst of a property tax revolt that may further gut local school funding. A rabble-rousing, union-advocating teacher friend of mine came out of the same public schools as me, and she now teaches at a private school, primarily to pay for the discounted tuition her daughter receives.

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I’ll soon have skin in this debate myself. I’m expecting my first child at the end of this year, and if I didn’t live hundreds of miles away from Florida, I would be looking into the academies, charters and parochial schools that serve the county’s booming population of wealthy remote workers trying to pull the ladder up behind them. 

Living in New Orleans, I’m lucky in a way. My child will be born into a city that has no traditional public school system; New Orleans went all-charter in 2019. The scramble to get kids into the best schools is baked in, with parents entering their grade-schoolers into school choice lotteries with little regard to geography, making it unlikely that my child will go to a school that mirrors the demographics of our neighborhood. That decision was made for us years ago. While I believe that public education should be funded at the state level, with equal per-student distributions of tax dollars coming from the top, I won’t be required to back that belief in equality up with action any time soon.

Hannah-Jones’ experiment might be novel, but the fight that broke out around it is familiar. You can see it anytime an outwardly progressive politician or commentator benefits from their personal wealth. If you really believe that America is in the grips of a homelessness crisis, why haven’t you opened your own home to the down-on-their-luck? How can an elected official like Sen. Bernie Sanders push for affordable healthcare for all, while benefitting from the Cadillac health plans afforded to Congress? If you’re such a believer in public schools, why would you balk at sending your child to a failing and underfunded institution?

Such arguments are meant to pare down complicated, systemic issues into a series of individual choices. They may vary on the specifics, but the intent is the same. Critics of progressive policy pushers want activists to shut up about privilege because it makes them uncomfortable. Having to think about the advantages and disadvantages baked into the system strays too far from the preferred framework of school choice advocates and other conservatives — that all people are equally free to choose the life they lead, and that failure to wring a good education out of our flagging system is entirely the fault of the individual.

It’s not a frame that public school advocates, Medicare for All true-believers or affordable housing rabble-rousers need to accept. The gap between progressive beliefs and reality is right there in one of its oldest and most popular bits of sloganeering: Another world is possible. Admitting that it’s not here yet is the first step to fighting for it.

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Science fiction’s superpower isn’t thinking up new technologies – it’s thinking up new social arrangements for technology. What the gadget does is nowhere near as important as who the gadget does it for and who it does it to. Your car can use a cutting-edge computer vision system to alert you when you’re drifting out of your lane – or it can use that same system to narc you out ...Read More

If there’s one thing I can’t abide, it’s nontechnical technothrillers. You know the trope: “We’ve got eight minutes to crack this mainframe, but it’s protected with encryption that is rated for ten minutes. We’re gonna have to hack really hard. Come on, hacker, HACK AWAY!”

Technothrillers are consumed by an increasingly computer-savvy audience, which means that the kind of technical elision and corner-cutting that dominates the field grows thinner by ...Read More

If a group of people have been trying to get something done for some time without success, there are two possibilities: Either they’re failing because of bad tactics, or they’re failing because they simply lack the power to achieve their goals. When things start changing in big, dramatic ways, that means that some group in society has either discovered a new tactic, or they’ve found some new coalition partners.

Most ...Read More

In my new novel Picks and Shovels, we learn the origins of Martin Hench, my bestselling, two-fisted, scambusting forensic accountant who debuted in 2023’s Red Team Blues and whose adventures continued in 2024’s The Bezzle.

Marty’s origin story starts at MIT in 1982, where he joins the proud lineage of computer science students who flunk out of their degrees because they’re too busy hacking code to do their ...Read More

Let’s start with two obvious facts:

That means that every single policy question related to the internet will have:

With that out of the way….

Late last August, Pavel Durov – the billionaire owner of the Telegram app – was arrested by French authorities after he landed his private ...Read More

There are many ways to cleave the views of the political right from the political left, but none is so science fictional as the right’s confidence in the role of individual self-discipline on one’s life chances. Dip into any political fight about crime and poverty and you’re sure to turn up someone confidently asserting that these social ills are rooted in impatience. Poverty, we’re told, is rooted in an unwillingness ...Read More

No one was more surprised than I was when the American Dialect Society named ‘‘enshittification’’ – my dirty little coinage to describe how everything on the internet is (suddenly, simultaneously) getting (much) worse – to be its Word of the Year. But though the news was a surprise, it was a very pleasant one.

My early writings on enshittification focused on its symptoms, the way platforms decay. The progression of ...Read More

In conflict, we find clarity.

We all hold contradictory views: We love our families, but they drive us crazy. We want more housing in our cities, but we don’t want our property values to decrease with expanded supply. We want better schools, but we recoil from a 0.1% municipal levy to fund them.

It’s normal to hold contradictory views, but when those views come into conflict, how we act shows ...Read More

Of course AI is a bubble. It has all the hallmarks of a classic tech bubble. Pick up a rental car at SFO and drive in either direction on the 101 – north to San Francisco, south to Palo Alto – and every single billboard is advertising some kind of AI company. Every business plan has the word “AI” in it, even if the business itself has no AI in ...Read More

It’s tempting to think of the Great Enshittening – in which all the inter­net services we enjoyed and came to rely upon became suddenly and irreversibly terrible – as the result of moral decay. That is, it’s tempting to think that the people who gave us the old, good internet did so because they were good people, and the people who enshittified it did so because they are shitty people. ...Read More

I was surprised as anyone when I found myself accidentally using a large language model (that is, an “AI” chatbot) to write some prose for me. I was twice as surprised when I found myself impressed by what it wrote.

Last month, an airline stranded me overnight in New York City when my flight to LA was canceled due to an air traffic control snafu. The airline rep at the ...Read More

On June 20, 2023, I will be awarded an Honourary Doctor of Laws from York University’s Faculty of Liberal Arts and Professional Studies, in Toronto, Canada. The text below is the speech I will give.

Goodness me, it is a gigantic honour to be here today, and to be recog­nized in this way. I’m profoundly grateful to the faculty and administration here at York, and to my friends and family ...Read More

Within the very first year of operation, 1878, Bell’s company learned a sharp lesson about combining teenage boys and telephone switch­boards. Putting teenage boys in charge of the phone system brought swift and consistent disaster. Bell’s chief engineer described them as ‘Wild Indians.’ The boys were openly rude to customers. They talked back to subscribers, saucing off, uttering facetious remarks, and generally giving lip. The rascals took Saint Patrick’s Day ...Read More

As I type these words, a mass exodus is underway from Twitter and Facebook. After decades of eye-popping growth, these social media sites are contracting at an alarming rate.

In some ways, this shouldn’t surprise us. All the social networks that preceded the current generation experienced this pattern: SixDegrees, Friendster, MySpace, and Bebo all exploded onto the scene. One day, they were sparsely populated fringe services, the next day, every­one ...Read More

If the bullies at the school gate steal your kid’s lunch money every day, it doesn’t matter how much lunch money you give your kid, he’s not gonna get lunch. But how much lunch money you give your kid does matter – to the bullies. Hell, they might even start a campaign: “The chil­dren of Jack Valenti Elementary School are going hungry! Congress must step in to give those kids ...Read More

“Five thousand quatloos that the newcomers will have to be destroyed.”

Quatloos. Credits. Euros. Dollars. Dogecoin.

Wait, Dogecoin?

At some point in your life, you’ve probably asked yourself, “What is money?” There’s something existential about pulling a bank-note out of your wallet and asking yourself, “Why does so much of my wak­ing life revolve around getting more of these slips of green paper?” (Outside of the USA, you may ask ...Read More

We’re all trapped on a bus.

The bus is barreling towards a cliff.

Beyond the cliff is a canyon plunge any of us will be lucky to survive.

Even if we survive, none of us know how we’ll climb out of that deep canyon.

Some of us want to yank the wheel.

The bus is going so fast that yanking the wheel could cause the bus to roll.

There might ...Read More

Greetings from the past.

I write these words six weeks before you will read them. I used to do this all the time, back in the glory days of print. Hell, I spent most of the ’90s writing a monthly guide to interesting websites, which came out two months after I submitted it.

I’ve been writing six columns per year for Locus for fourteen years and I have not missed ...Read More