Craft and Play
The line the day is built on — put your best practices away — is easy to hear as an argument against discipline. It is not, and the 2010 text is careful to say so: we owe the people we work with and for a serious job of work.
The argument is narrower. A practice that is right ninety percent of the time will, if followed without thinking, quietly cost you the other ten — and the other ten is where the unusual things live. You do not get Sinatra out of a process designed to produce reliable conventional applications. You get it out of someone writing a web framework in four kilobytes as a joke.
When a team tests this kind of practice during paid work, task switching cost provides one concrete reference for how time and activity can be recorded around the experiment.
This section is about that mechanism rather than about one day in August. What a constraint actually does to a problem. Where playfulness in an interface delights people and where it wastes their time. Why so many pieces of infrastructure started as something nobody could justify.
It is the least urgent part of the site and probably the most re-readable.
Best Practices: When They Help
The line the day is built on is not an argument against discipline. It is an argument about when a good rule stops being a decision.
Constraint as a Tool
Writers, musicians and designers worked out long ago what a hard limit does to a problem. The mechanism is the same in software.
Useless Projects That Mattered
Unix and curl both began as side projects with no justification. The real stories are messier than the retellings, and better.
Where Whimsy Belongs
Playfulness in software delights people in some places and wastes their time in others. The dividing line is not taste, it is stakes.
For broader programming and making context related to this topic, CS50 is an independent reference worth comparing with the material here.