Stuff I've Loved

So I did all my college applications on my own, negotiated all my student loans on my own, and handled all the logistics on my own. (This is a superpower that all ECI’s (Eldest Children of Immigrants) possess. Do not fuck with us. We can do paperwork, we can forge the signature of every adult in a three mile radius, and we are not afraid of negotiating with utility companies.) By the time my parents returned from their vacation I was safely tucked away in a college dorm, learning how to hack a cigarette machine. The first time

A useful starting point is to think of these categories along two axes: impact in case of success, something related to return on investment, and probability of success, directly related to something called epistemic risk, that is uncertainty about whether the knowledge needed to solve a problem even exists yet. These two axes together define a space that innovation portfolio researchers have mapped into four quadrants, a framework developed by Robert G. Cooper and colleagues for R&D portfolio management. The quadrants have names that are worth knowing: Pearls (high probability of success, high impact), Oysters (low probability of success, high impact if achieved), Bread and Butter (high probability of success, low impact), and White Elephants (low probability of success, low impact). If you wonder about the term “white elephants”, it comes from the legend of those sacred animals that existed in parts of Asia, and that a king would gift to courtiers he wished to ruin: too expensive to maintain, too sacred to put to work. The goal of any healthy technology portfolio is to cultivate Pearls, pursue Oysters selectively, keep Bread and Butter work from crowding everything else out, and eliminate White Elephants as quickly as possible. Mapping the three categories of technical work onto this space gives us a useful picture.

research, R&D, and product engineering are not simply the same activity performed by the same people at different speeds and under different levels of pressure. A good friend of mine, and an amazing technologist, once joked that engineering runs on quarters of three months, while research runs on a quarterly of a century timeline. In reality they are fundamentally different jobs, with different goals, different success criteria, and people with different motivations and experience.

Research lives in the Oyster quadrant. The horizon is long, often several years, epistemic risk is high, and there is no guarantee of practical output. You can see the potential, but finding the pearl requires years of work, wrong turns and backtracks, and constant awareness of what other researchers around the world are doing. That is why research cannot happen in isolation. Publishing results, attending conferences, and engaging with the broader scientific community are not optional extras. They are how researchers know where the field is, avoid duplicating work already done elsewhere, and attract the collaborators and critics that sharpen their own thinking. The early work on transformer architectures before anyone knew whether scaling would yield emergent capabilities was an Oyster. The initial bets on large language models, the first serious work on interpretability, the attempts to build world models that represent reality rather than language about reality: these are Oysters. Some will open. Many will not. The frontier labs betting that transformer-based LLMs have a fundamental ceiling, and pursuing entirely different architectures or learning regimes, are running the deepest Oysters in the current landscape. Same industry, similar talent pool as their Pearl-type competitors, completely different relationship to epistemic risk, and completely different motivations. That difference matters enormously for how you fund them, manage them, and judge their progress.

Fast is better than slow. That’s just how it is. Your job is to take everything you can already do and do it faster. If you can embrace the idea that fast is intrinsically better than slow, you’re halfway home. If you can get an entire team of players to embrace that idea, you’re going to win a lot of games. All other things being equal, if I can get the ball from Point A to Point B with one touch, it is better than getting it there in two touches. Why? Because one touch is faster than two touches, and fast is better than slow. — Dan Blank, Soccer IQ

Pick your battles. When it comes to collaboration, don’t waste time bikeshedding. If your PR reviewer wants you to change something, it’s almost always faster to do what they’re asking than to argue about it. 95% of the time, the differences are so minor that it’s barely worth discussing. Save your time and energy for the 5% that matter. The same thing applies when you’re reviewing — don’t waste your time on inconsequential things. I’m definitely not saying you should rubber stamp everything; I often leave comments suggesting better names, or other ways to do things, but leave the final decision up to the author. I think at least 50% of my reviews are “LGTM with comments” — in my opinion, this gives you most of the benefits of code review without letting it suck up too much time (for you or your teammates).

Don’t question why. Fast is better than slow. That’s just how it is. Your job is to take everything you can already do and do it faster.

When you strip away the product marketing and the dev relations and the blog posts and the funding rounds and the fuckery-upon-fuckery of it all, we’re left with a simulation of collective engagement - but very little else. Transparency got confused with progress, visibility got confused with accountability, and being included in the thread became the same thing, socially and organizationally, as owning the outcome.

Once that confusion set in at the cultural level it became nearly impossible to dislodge. The feeling of collaboration is pleasant in a way that personal accountability can never be. Owning something means you, specifically and visibly you, can fail at it, specifically and visibly, in ways that attach to your name. Collaborating means the failure belongs to the process. So everyone chose collaboration, and we called it culture.

was changed by the experience of meeting the people who invited Christoffer and me in. Our trip helped me realize that the world isn’t like one of those games with predetermined levels; it is a game of generated landscapes where the world keeps growing the further you go. You can go out and talk to people and do stuff, and the world opens up vista after vista. Or, as Werner Herzog likes to say, “the world reveals itself to those who travel by foot.”

There is a loop here, which for me started when Christoffer and I bicycled to Finland: You reach out to the world, trusting it, and then you end up in situations and meet people who surprise you and expand your sense of possibility, which gives you more landscapes to explore, and so on and on.

What I learned on our trip to Finland wasn’t about how to travel but how you can relate to the world. I learned that the world (like people!) grows bigger, more varied, and interesting if I’m open, playful, and trusting

After I die, I’m not expecting the world, but this business about the afterlife is more complicated than what they describe in the Bible. The experts say more than 100 billion humans have died. If you’re looking for a buddy to have a beer, like jazzman Dave McKenna or writer Jerry Murphy or possibly Peter Falk who played Columbo, how are you going to find him in a mob of 100 billion people?

If you’re lucky enough to be able to, find yourself a position on a team, at a company, or in a lab that owns something big. I think the Amazon pattern of having the same team build and operate systems is ideal for learning. If you can, carry a pager. Be accountable to your team and your customers that the stuff you build works. Reality cannot be fooled. I often disagree with my past self4, but I still believe this is the best path to learning to build big systems. Be an owner, be a builder, be hands-on and responsible. Carry a pager. Own a deadline. I don’t think that path has changed much. The day-to-day has changed, and will change more, but the high-level picture remains the same.

There is something profoundly irritating about how normal everything looks when you receive bad news. The kettle still works. The bin still needs to be taken out. The neighbour still slams his door. You still have to decide what to have for dinner. And then there comes the time, after you’ve heard the bad news, when the concept of geography itself becomes offensive.

There has been bad news before, of course. Mostly from me. Breakups. Job losses. Petty theft. The sort of adult crises that feel tortuous and dramatic at midnight but manageable by morning. But this one—the fact that my mum, my wonderful mum, has breast cancer—does not feel manageable by morning. Self-sufficiency is extremely elegant when the crisis can be handled from afar. When you can say, “I’m sorry,” or “That’s awful,” and then hang up and re-enter your own life. It is less elegant when what you want to do is sit in the same room and watch someone breathe. When my mum called to tell me her news, I said, “Okay.” I think I said it twice. I have become very good at saying “Okay” in a tone that suggests gentle authority. After we hung up, I sat very still for a few minutes, as though stillness might prevent escalation. Then I stood up went to the kitchen to put the kettle on, because this is what you do when something happens that you cannot fix immediately: you boil water. The kettle boiled normally. There was enough milk for my tea. The first sips I took did not burn the roof of my mouth. I found the entire affair heinously offensive in its normality. In the days that followed, I developed new habits. I have been walking in large loops around my neighbourhood. Not briskly, not purposefully—just in circles. On any given day, I’ll pass the same off-licence three to sixteen times. I’ll notice the same dog tied to the same railing. I’ll see the same benches, the same potholes, the same patches of dirt, the same grey skies. If the sun has set, I’ll peer into people’s lit windows to witness their life and then, for a fleeting moment, become enraged by my own.

Too, my mother does not dramatise. She refuses to spiral. She tells me what the doctors tell her; she tells me what they don’t. She sounds, for the most part, like herself. This—the latter—is both comforting and unsettling, mostly because there is something quite unnerving about a parent remaining calm when you would quite like them to panic, just briefly, so you can calibrate your own panic accordingly. Instead she says, “It’ll be fine,” and I nod, though be both know that “fine” is one of the most flexible words in the English language. (It turns out that once you enter the vocabulary of illness, other words start to wobble.)

And underneath all of it is a single, deeply inelegant thought: I do not want to lose her. My mum. My wonderful mum. As far as thoughts go, it is not particularly sophisticated. It is not narratively interesting. It is not even particularly articulate. But it is persistent and it is true. Self-sufficiency, I am learning, is not the same thing as preparedness. You can be independent. You can be competent. You can be impressively self-contained. None of this prevents the primitive terror of imagining a world—your world—changed and rearranged beyond recognition. But for now, my mum says, “It’ll be fine.” For now, I nod. For now, the kettle still works.

In advance of each Town Hall, leadership would pick a few people for these “get to know the team” panels. The questions were personal, and yet everyone’s answers always circled back to work. The host would ask, “Who’s on your Spotify Wrapped this year?” and some middle manager would gush, “Like alllll classical because it helps me focus!” SHUT THE FUCK UP. JUST SAY TAYLOR SWIFT AND WALK THOSE DUSTY ROTHYS BACK TO YOUR CUBICLE.

They’re right about one big thing: our moral mettle will be tested by dilemmas so small that they’re nearly imperceptible.

I’ve come to think of this as the Bluetooth Test: when you’re given the smallest amount of power, do you use it to make things nice for everybody, or just yourself?

If you’ve signed up to offer an attention-luxury good, you undermine it when you also try to make it quick and convenient.

‘wasting’ our attention on nuance, narrative, experiences and everything except the checkbox takeaway, we’re sending a message to ourselves and others. A message about allocating our time to something beyond optimized performance or survival. If you’ve signed up to offer an

However, the power of responsiveness extends past the domain of social charm, it’s about more than making a giant pile of money selling CDs. I would argue that responsiveness is a core human need/desire. It is, perhaps, required for happiness. People are happy enough rich, and people are happy enough poor. But it’s hard to imagine anyone happy without a feeling that their actions have some impact, however small. Even if you’re not going to be remembered by history, you want to be remembered by your barista. The prisoner, though largely robbed of power, is probably happier if he can vex his captors, or skirt the rules somehow. Life is good if it squishes nicely when you poke

It is worth mentioning that this editor is an old college friend; we’ve driven across the country, been pantsless in several nonsexual contexts, and accidentally hospitalized each other in good fun. He is now a respectable homeowner and family man; I am not. So I couldn’t help but wonder: is there something condescending about this assignment? Does he consider me some sort of amusing and feckless manchild instead of a respected cartoonist whose work is beloved by hundreds and has made me a thousandaire, who’s been in a committed relationship for 15 years with the same cat? My weird touchiness on this issue — taking offense at someone offering to pay me money for my work — is symptomatic of a more widespread syndrome I call “The Referendum

It’s true that my romantic life has produced some humorous anecdotes, but good stories seldom come from happy experiences. Some of my married friends may envy my freedom in an abstract, daydreamy way, misremembering single life as some sort of pornographic smorgasbord, but I doubt many of them would actually choose to trade places with me. Although they may miss the thrill of sexual novelty, absolutely nobody misses dating

Most of my married friends now have children, the rewards of which appear to be exclusively intangible and, like the mysteries of some gnostic sect, incommunicable to outsiders. In fact it seems from the outside as if these people have joined a dubious cult: they claim to be much happier and more fulfilled than ever before, even though they live in conditions of appalling filth and degradation, deprived of the most basic freedoms and dignity, and owe unquestioning obedience to a capricious and demented master.

master. I have never even idly thought for a single passing second that it might make my life nicer to have a small, rude, incontinent person follow me around screaming and making me buy them stuff for the rest of my life. [Note to friends with children: I am referring to other people’s children, not to yours.] But there are also moments when some part of me wonders whether I am not only missing the biological boat but something I cannot even begin to imagine — an entire dimension of human experience undetectable to my senses, like a flatlander scoffing at the theoretical concept of sky.

Yes: the Referendum gets unattractively self-righteous and judgmental. Quite a lot of what passes itself off as a dialogue about our society consists of people trying to justify their own choices as the only right or natural ones by denouncing others’ as selfish or pathological or wrong. So it’s easy to overlook that hidden beneath all this smug certainty is a poignant insecurity, and the naked 3 A.M. terror of regret

The problem is, we only get one chance at this, with no do-overs. Life is, in effect, a non-repeatable experiment with no control. In his novel about marriage, “Light Years,” James Salter writes: “For whatever we do, even whatever we do not do prevents us from doing its opposite. Acts demolish their alternatives, that is the paradox.” Watching our peers’ lives is the closest we can come to a glimpse of the parallel universes in which we didn’t ruin that relationship years ago, or got that job we applied for, or got on that plane after all. It’s tempting to read other people’s lives as cautionary fables or repudiations of our own.

One of the hardest things to look at in this life is the lives we didn’t lead, the path not taken, potential left unfulfilled. In stories, those who look back — Lot’s wife, Orpheus and Eurydice — are lost. Looking to the side instead, to gauge how our companions are faring, is a way of glancing at a safer reflection of what we cannot directly bear, like Perseus seeing the Gorgon safely mirrored in his shield.

Or, to phrase it differently, form-context-fit is a way for us to judge if a specific solution to a problem is good. And what Alexander said was that a design is good if and only if the form (of the solution) fits the context (of the problem).

This is a common and strong human tendency: to distort our understanding of the problem to make our preconceived solution look like the right answer. Obviously, this makes it harder to see what the right solution is. You won’t be as attentive to the landscape if you hide your face behind a badly drawn map.

Every single wart that annoys us today, used to be a reasonable feature that someone relied on in their production code. Every wart we see today is a testament to the care the maintainers put into backward compatibility. If we choose a technology today, we want one that saves us from future maintenance by keeping our wartful code running – even if we don’t yet know it is wartful. The best indicator of this is whether the technology has warts today.

. The larger social truth Luke was touching on, that being good at passing tests has relatively little to do with being good at what those tests are supposed to be testing, in the end came to haunt my entire experience of learning to drive

Dread is always the product of imagination. You see the bad consequence coming and the image paralyzes your judgment. A

Driving, I realized, isn’t really difficult; it’s just extremely dangerous. You hit the gas and turn the wheel, and there you are—in possession of a two-ton weapon capable of being pointed at anything you like, at any speed you can go at, just by pressing a pedal a little bit harder.

The point of living in a technologically advanced society is that minimal effort can produce maximal results. Making hard things easy is the path to convenience; it is also the lever of catastrophe. T

e was sound, solid, in his role as a dean paterfamilias to a campus—all things I never hoped to be. My not driving was, in some sense, a response to his driving all the time. We make ourselves in our father’s sunshine but also in his shadow: what he beams down we bend away from

car was the means not just to autonomy—though it was that: you could get behind the wheel and go to Atlantic City, to Provincetown, even to old Quebec—but to privacy. It enabled a lower-middle-class kid in a fractious, noisy extended family to be alone with his thoughts. He said to me once, when I was small, “You know, you can drive right across the country now without a stoplight

(I suspect that the significant things we say to our children usually vanish, while incidental oddities linger.

If driving mattered so much to him, why would it not to me? Had he failed me in some way, or had I failed him in some way I was still not ready to recognize?

I had to persuade myself that what I had grown to attribute to automatic forces was actually the work of agency.

, I not only began to enjoy it but also began to like cars, and to see that driving is one of the last democratic things we do.

. “Sir, the reason is very plain,” he said. “Knowledge is of two kinds. We know a subject ourselves, or we know where we can find information upon it.” Almost all of our useful knowledge is potential knowledge

The potentials may serve merely as vicarious experience, but almost all experience is vicarious: that’s why we have stories and movies and plays and pictures. It’s why we have drive-in movies in summer towns. We expand our worlds through acts of limited empathy more than through plunges into unexpected places

The highlights of life are first unbelievably intense and then absurdly commonplace.

Having a child born is a religious experience. But everybody has kids. Everybody drives, and now I can, too. That’s all, and enough. Now I can drive straight across the country, without a stoplight. I don’t think I ever will. But at least I know I can

We go on being driven and sorted, until at last we’re sorted out, and driven home