Books
A few books that I've read and recommend. Some of them aren't specific to software development, but are still worth reading, perhaps even moreso.
Orbiting the Giant Hairball, Gordon MacKenzie
Easily my favourite business book. At the very least, I thoroughly enjoyed reading it. Gordon MacKenzie spent thirty years at Hallmark Cards, which accumulated a certain amount of bureaucracy, as any company does over time as it grows. In the book, he describes how he benefited from the security of working at a large organisation, while maintaining his creativity and avoiding being sucked into the hairball of bureaucracy.
There's little by way of directly actionable advice in the book, but even if we don't have our own hairballs to contend with, this is an excellent meditation of the nature of creativity.
The Mythical Man-Month, Fred Brooks
The Mythical Man-Month is perhaps the most famous software engineering book. Originally published in 1975, the technological references aren't exactly bang up-to-date. However, much of the insight is as true today as it was then. As Fred Brooks observes, failures on software projects are often for social rather than technological reasons. When reflecting on your latest failed project, you can either take solace in being the latest in a long line of extremely clever people to make the same mistakes, or weep at how little we seem to have learnt in the intervening decades.