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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