in 2023, I switched gears to emphasize intimacy. Instead of statistical analysis and summative interviews, I sat next to individuals for hours, as they used one-off prototypes which I’d made just for them. And I got more insight in the first few weeks of this than I had in all of 2022

I’d been building systems and running big experiments, and I could tell you plenty about forgetting curves and usage patterns—but very little about how those things connected to anything anyone cared about.

I could see, in great detail, the texture of the interaction between my designs and the broader learning context—my real purpose, not some proxy.

Single-user experiments like this emphasize problem-finding and discovery, not precise evaluation.

a good heuristic for evaluating my work seems to be: try designs 1-on-1 until they seem to be working well, and only then run more quantitative experiments to understand how well the effect generalizes.

My aim is to invent augmented reading environments that apply to any kind of informational text—spanning subjects, formats, and audiences. The temptation, then, is to consider every design element in the most systematic, general form. But this again confuses aims with methods. So many of my best insights have come from hoarding and fermenting vivid observations about the particular—a specific design, in a specific situation. That one student’s frustration with that one specific exercise.

It’s often hard to find “misfits” when I’m thinking about general forms. My connection to the problem becomes too diffuse. The object of my attention becomes the system itself, rather than its interactions with a specific context of use. This leads to a common failure mode among system designers: getting lost in towers of purity and abstraction, more and more disconnected from the system’s ostensible purpose in the world.

I experience an enormous difference between “trying to design an augmented reading environment” and “trying to design an augmented version of this specific linear algebra book”. When I think about the former, I mostly focus on primitives, abstractions, and processes. When I think about the latter, I focus on the needs of specific ideas, on specific pages. And then, once it’s in use, I think about specific problems, that specific students had, in specific places. These are the “misfits” I need to remove as a designer.

Of course, I do want my designs to generalize. That’s not just a practical consideration. It’s also spiritual: when I design a system well, it feels like I’ve limned hidden seams of reality; I’ve touched a kind of personal God. On most days, I actually care about this more than my designs’ utilitarian impact. The systems I want to build really do require abstraction and generalization. Transformative systems really do often depend on powerful new primitives. But more and more, my experience has been that the best creative fuel for these systematic solutions often comes from a process which focuses on particulars, at least for long periods at a time.

Also? The particular is often a lot more emotionally engaging, day-to-day. That makes the work easier and more fun.

Throughout my career, I’ve struggled with a paradox in the feeling of my work. When I’ve found my work quite gratifying in the moment, day-to-day, I’ve found it hollow and unsatisfying retrospectively, over the long term. For example, when I was working at Apple, there was so much energy; I was surrounded by brilliant people; I felt very competent, it was clear what to do next; it was easy to see my progress each day. That all felt great. But then, looking back on my work at the end of each year, I felt deeply dissatisfied: I wasn’t making a personal creative contribution. If someone else had done the projects I’d done, the results would have been different, but not in a way that mattered. The work wasn’t reflective of ideas or values that mattered to me. I felt numbed, creatively and intellectually.

Progress often doesn’t look like progressIt often feels like I’m not making any progress at all in my work. I’ll feel awfully frustrated. And then, suddenly, a tremendous insight will drive months of work. This last happened in the fall. Looking back at those journals now, I’m amused to read page after page of me getting so close to that central insight in the weeks leading up to it. I approach it again and again from different directions, getting nearer and nearer, but still one leap away—so it looks to me, at the time, like I’ve got nothing. Then, finally, when I had the idea, it felt like a bolt from the blue.

The same applies to writing. For example, when one topic doesn’t seem to fit a narrative structure, it often feels like a problem I need to “get out of the way”. It’s much better to wonder: “Hm, why do I have this strong instinct that this point’s related? Is there some more powerful unifying theme waiting to be identified here?”

Often I need to improve the framing, to find one which better expresses what I’m deeply excited about. If I can’t find a problem statement which captures my curiosity, it’s best to drop the project for now.

I’m much less likely to flinch away when I’m feeling intensely curious, when I truly want to understand something, when it’s a landscape to explore rather than a destination to reach. Happily, curiosity can be cultivated. And curiosity is much more likely than task-orientation to lead me to interesting ideas.

Savor the subtle insights which really do occur regularly in research. Think of it like cultivating a much more sensitive palate.

“Why is this so hard? Because you’re utterly habituated to steady progress—to completing things, to producing, to solving. When progress is subtle or slow, when there’s no clear way to proceed, you flinch away. You redirect your attention to something safer, to something you can do. You jump to implementation prematurely; you feel a compulsion to do more background reading; you obsess over tractable but peripheral details. These are all displacement behaviors, ways of not sitting with the problem. Though each instance seems insignificant, the cumulative effect is that your stare rarely rests on the fog long enough to penetrate it. Weeks pass, with apparent motion, yet you’re just spinning in place. You return to the surface with each glance away. You must learn to remain in the depths.”

Depth of concentration is cumulative, and precious. An extra hour or two of depth is enormously valuable. I reliably get more done—and with more depth—in that 6-7 hour morning block than I’d previously done in 9-10 hours throughout the day.This feels wonderful. By 2PM, I’ve done my important work for the day. I know that no more depth-y work is likely, and that I’ll only frustrate myself if I try—so I free myself from that pressureI notice that some part of me feels ashamed to say that I’m “done” working at 2PM. This is probably because in my previous roles, I really could solve problems and get more done by simply throwing more hours at the work. That’s just obviously not true in my present work, as I’ve learned through much frustration. Reading memoirs of writers, artists, and scientists, I see that 2-4 hours per day seems to be the norm for a primary creative working block. Separately, and I don’t want to harp on this because I want this essay to be about quality, not quantity, but: I think most people are laughably misled about how much time they truly work. In a median morning block, I complete the equivalent of 1225-minute pomodoros. When I worked at large companies, getting 8 done before 6PM was a rarity—even though I’d assiduously arrange my calendar to maximize deep work!. I take meetings; I exercise; I meditate; I go on long walks. I’ll often do shallower initial reads of papers and books in the afternoon, or handle administrative tasks. Sometimes I’ll do easy programming work. It’s all “bonus time”, nothing obligatory. My life got several hours more slack when I adopted this schedule, and yet my output improved. Wonderful!

no internet on my phone before I sit down at my desk. I don’t want anyone else’s thoughts in my head before I start thinking my own.

If I spend a working interval flailing, never sinking below the surface, the temptation is to double-down, to “make up for it”. But the right move for me is usually to go sit in a different room with only my notebook, and to spend the next working interval writing or sketching by hand about the problem.

Administrative tasks are a constant temptation for me: aha, a task I can complete! How tantalizing! But these tasks are rarely important. So I explicitly prohibit myself from doing any kind of administrative work for most of the morning. In the last hour or two, if I notice myself getting weary and unfocused, I’ll sometimes switch gears into administrative work as a way to “rescue” that time.

I’ve noticed that unhealthy afternoon/evening activities can easily harm the next morning’s focus, by habituating me to immediate gratification.

most of the benefit just seems to come from regularly reflecting on what I’m trying and what’s happening as a result. It’s really about developing a rich mental model of what focus and perseverance feel like, and what factors seem to support or harm those states of mind.

Sometimes I just need to execute; and then traditional productivity advice helps enormously. But deep insight is generally the bottleneck to my work, and producing it usually involves the sort of practices I’ve described here.