The best classic software books that are still worth reading

In my consulting gigs, I come across plenty of clueless remarks. Here's a classic one: “We're falling behind schedule, so let's hire more coders.” Or a more recent gem: “We'll be ten times more productive if we generate code with AI.”

When I encounter such nonsense, I don't facepalm or cringe. Instead, I put on my poker face and drop a quote from The Mythical Man-Month.

In an industry where last year’s book is already outdated, Fred Brooks' collection of essays has been a guiding light for nearly half a century. His aphorisms have become legendary. “The bearing of a child takes nine months, no matter how many women are assigned.” “Adding manpower to a late software project makes it later.” “There is no silver bullet.” The list goes on and on.

John Carmack, one of the greatest programmers of our times, used to revisit this book every year or two. We should all do it.

Here is a confession: I never got around to reading The Pragmatic Programmer. Not cover to cover, I mean. I read it in fragments, a page here and a chapter there.

I was usually prompted by a reference in a blog post or a conference talk. It's hard to read about programming today without stumbling on quotes from this 1999 book. The Pragmatic Programmer is choked full of ideas that are thought provoking, beautifully discussed, and, yes, pragmatic.

Riding on this book's success, Andy Hunt and Dave Thomas went on to become publishers. When it came time to write my own books, I jumped at the chance to publish with them. It's not every day that you get to work with your heroes!

If one author influenced my way of thinking about software, that’s Martin Fowler. From planning to architectures, his insights are embedded in every line of code I write. I was certain that one of his books would make my list.

But which one? Let’s face it–many of Fowler's books feel dated today. Not because his ideas became obsolete, but because they're now taken for granted. Who needs to re-read a book like Refactoring, when we all have a refactoring menu at our fingertips?

So I settled on this book. It’s a catalog of patterns, but one of the best. And don’t be misled by the word “enterprise” in the title: even lightweight patterns such as Active Record were popularized by this book.

Whether or not you work in a large company, this is still an essential collection of knowledge, written in Fowler’s signature clean style.

Few people want to grow up like their parents. In the early 2010s, many programmers scoffed at the design principles of the ‘90s. Why should anyone care about the nuances of object-oriented design? That’s such a Java thing to bother with!

To seasoned developers, this rejection felt like a baby and bathwater situation. Then Sandy Metz came to the rescue. Her book persuaded younger developers (or at least, those in the Ruby community) that those old ideas were still valuable.

Practical Object-Oriented Design in Ruby traced a straight line from the pioneering times of Smalltalk, through the years of the software craftsmanship movement, directly to modern programming.

It’s a timeless book in the best sense of the word: it would have felt relevant back in the 90s, or when it was published, or today. Few people want to grow up like our parents–but as it turns out, we all do.

If you check out Amazon’s best selling books on object-oriented design, you might see a relic from 1995 still hanging near the top: "Design Patterns". That book transformed software design. Its four authors will forever be known to my generation as the “Gang of Four".

Some of the original patterns may feel outdated today, but others remain essential. Pity that the book itself is such a tough read. Good thing that another "gang of four”, spearheaded by the excellent Kathy Sierra, gave us this lighthearted take on the original patterns.

The Design Patterns book was a densely packed truck of ideas. By comparison, Head First Design Patterns is a whimsical bumper car. It’s quirky and accessible, which some serious programmers found off-putting: “It’s a book for teenagers!“, they griped.

Yes, it’s not for everybody. But it’s fun, unassuming, and it teaches important concepts. So it makes my list.