Last year, I quit my job to work on a project of my own. This was February of 2023. ChatGPT had come out in the fall of the previous year and I was thrilled by the possibilities of LLMs (I still am), but that’s not the whole story. The summer before, I revisited a pivotal influence of mine: Ted Nelson’s Project Xanadu. In short, Nelson had the idea that hypertext (a term he coined) should be baked into the substrate of word processing, not merely bolted on at publication time—and he pursued this project relentlessly through the formative decades of personal computing. That summer—before I got excited about LLMs—I began to see how establishing a few key primitives and nailing the bookkeeping of a word processor could unlock a very powerful workspace for text. In other words, I began to understand the possibilities that had tantalized Ted Nelson all those years.

The funny thing is, I...

One of the coolest aspects of software development is the way it makes really big theoretical questions around system design totally accessible. Every teenager building a web app is deploying an ad hoc bureaucracy of computer processes. As you get more experience, you start to think critically about how it all fits together.

I remember reading “The Rise of Worse is Better” a decade ago. The first time I read it, it felt like a call to action. It’s the story of how less elegant designs have come to dominate the world of computing, outcompeting and rendering irrelevant so many other, more brilliant systems. I felt compelled to investigate these alternate threads of history. I wondered what the world would look like if The Right Thing had won at each step along the way to our modern tech landscape.

Toward the end of high school I started taking math at The Ohio State University. This...

Apple’s most iconic ad featured a cast of famous misfits, rebels, and dreamers. I think Michel Foucault would’ve been a worthy addition. The campaign linked the company to a certain philosophy of the world—and this worldview, with its particular understanding of social change, has a lot in common with the work of Michel Foucault and the other founders of critical theory. A later interview with Steve Jobs, in which Steve says the following, makes the connection clear:

When you grow up you tend to get told that the world is the way it is and your life is just to live your life inside the world. Try not to bash into the walls too much. Try to have a nice family life, have fun, save a little money. That’s a very limited life. Life can be much broader once you discover one simple fact: Everything around you that you call life was made up by people that were no smarter than you. And you can...

In the twentieth century space exploration reached its zenith during the Cold War. At this point, space exploration was revealed to be about two things above all. First, space was made the arena for a new sort of competition between nations. While America and Soviet Russia were engaged in a cold war, space exploration became the scale by which to measure the effectiveness of the two countries and, in fact, by which to measure the effectiveness of their respective paradigms of governance. America set out to prove that a free society will ultimately outperform a centrally-planned communist regime. This was not obvious.

Additionally, space was rightly perceived as a realm with great power for war and peace. The conquest of space as satellites were pushed into orbit around the planet was the source of great anxiety. Those countries that could do this first would gain the higher ground...

Nowadays everything seems replaceable. Discussion of the successors to credit cards and gas-powered cars is common in a way that discussion of those to paper currency and oil lamps never was. The status quo is so quickly shifting that any everyday annoyance is seen as a gap to be quickly filled, an opportunity waiting for any company that will seize it.

Of course, however, not everyone who notices such an annoyance will jump to form a company around it. Most people never really pursue these ideas; they acknowledge them and patiently await their solution by someone else. Those who do attempt a solution will only do so up to a certain cost. It’s human nature to be at least somewhat risk averse. Your valuation of cost, however, is not strictly a function of missed opportunities or necessary resources; this blow can often be softened when a project is compatible with your identity and...