My Favorite Essays

These are the most important essays I’ve read that have shaped my understanding of the online world and software development as a profession.

On the internet and people

Essay Title	Author	Summary
The Tyranny of Structurelessness	Jo Freeman	Contrary to what we would like to believe, there is no such thing as a structureless group. Any group of people of whatever nature that comes together for any length of time for any purpose will inevitably structure itself in some fashion.
I Hate the News	Aaron Swartz	Reading the mainstream news doesn’t give us any benefits because we can’t act on it. We’re made to feel helpless. We’re better off reading a book.
A Group is Its Own Worst Enemy	Clay Shirky	Groups behave both as groups and as individuals, meaning that groups online are constantly in conflict with each other and themselves.
The Web is a Customer Service Medium	Paul Ford	“Why Wasn’t I Consulted” is an important question to ask when being online
I tweet honestly, I tweet passionately	Alice E. Marwick, danah Boyd	We have different contexts depending on which people we spend time with. The internet has erased that.
Reflections on the programming life	Ellen Ullman	What programming is like at the micro level
The Anaconda and the Chandelier	Perry Link	Why the threat of surveillance is scarier than actual surveillance
In Praise of the Flaneur	Bijan Stephen	Walking purposelessly around the internet is no longer an option
Woods+	Paul Ford	It’s about Google+, but even more.
The Submarine	Paul Graham	How marketing and newspapers work
How Apple and Amazon Security Flaws Led to my Epic Hacking	Mat Honan	On Apple IDs and digital identity
You Have Two Jobs	Jacob Kaplan-Moss	At work, you need to be good at your job and be easy to work with.
The Wolf	Michael Lopp	What makes up a 10x developer
Talking about Large Lanugage Models	Murray Shanahan	The more adept LLMs become at mimicking human language, the more vulnerable we become to anthropomorphism, to seeing the systems in which they are embedded as more human-like than they really are.
The Engineering-Manager Pendulum	Charity Majors	You can switch between both in your career and that’s mostly ok.
How to Ask Good Questions	Julia Evans	You have to research a problem before you need to seek out help
The B-Lane Swimmer	Holly Witteman	People of different skill levels behave differently to one another.

On programming

Essay Title	Author	Summary
Parse Don’t Validate	Alexis King	What the title says
Statistical Modeling: The Two Cultures	Leo Breiman	There are people who create simple models via data and complex models via algorithms
Choose Boring Technology	Dan McKinley	What the title says
Grug Brained Developer	Grug	Complex is bad