“Out of the Tar Pit” is an old paper, but worth a read never the less. The paper was picked up in more recent years by Hacker School, and also “10 Technical Papers Every Programmer Should Read (At Least Twice), and more recently, Brian Gesiak.
Since Brian has offered a few interesting call-outs already, I’ll only offer a few additional thoughts/quotes:
Page 1: The biggest problem in the development and maintenance of large-scale software systems is com- plexity — large systems are hard to understand
Page 2: Complexity is the root cause of the vast majority of problems with soft- ware today