Programming

The Wizard Book is a classic that basically "builds" programming as a concept.

(it is very technical though. So not sure it's something you're looking for)

A declaration of independence of cyberspace by John Perry Barlowe

Not really related to political philosophy but Uncle Bob's book on the philosophy of a good programmer also comes to mind: Clean Coder

A Philosophy of Software Design

Author's talk about the same topic

A not technical book about programming I would suggest: https://themediocreprogrammer.com/what-is-the-mediocre-programmer.html#what-is-the-mediocre-programmer

Not a direct answer to your question but here's what I've learned and am learning:

It all boils down to "finding the right balance between the costs of implementation, the value the implementation offers given the circumstances and constraint." Essentially, the foundational guideline of engineering across all engineering principles.

Usually every decision brings about about a series of advantages/improvement but it's important to remember that "one must lose in order to gain."[1] That is, every improvement (value) comes at a price (cost). Unlike other principles of engineering (which are closer to bare maths), software engineering more closely resembles something intuition-based like art. That is what makes it difficult to see the values and costs and measure them. It takes lots of practice and introspective and extrospective (!) effort; doing things and potentially making mistakes and learning from them is as important as observing others do things and make mistakes.

In other words, it boils down to honing your intuition to "do the right thing, at the right time, the right way."

PS: Please note that I used the word "right" and not "correct."

[1] Dialectically speaking, every material good contains w/i itself its own seeds of destruction 😆

Weinberg boiled it down to a single axiom for me: "If builders built buildings the way programmers wrote programs, then the first woodpecker that came along would destroy civilization." I'm not sure if they're still in fashion, but two other things that inspired me were The Cathedral and the Bazaar and the front material of the original Gang of Four book *Design Patterns."