Great Writing — Why the Lucky Stiff

Programming computers is a serious business. It is a business involving tens of thousands of workers across thousands of companies, all busy making and spending hundreds of billions of dollars. It is an industry that I happen to have been in for most of my adult life.

You can see the seriousness of software development in the books about programming. They’re often big, weighty tomes, packed full of material that will be outdated within a few years.

What you do not find in typical software books is humor, silliness, or even mild fun. While programmers might occasionally wax poetic about “code as art,” it is art underpinned by logic and exacting precision. Software must be precisely written in order to work correctly. Unnecessary ornamentation is not generally considered a good thing when it comes to programming.

Why’s (Poignant) Guide to Ruby

Why the Lucky Stiff is a programmer. Or at least the online pseudonym of one (often shortened to just _why). I first discovered him the way many people did, through a book that he wrote called Why’s (Poignant) Guide to Ruby.

This strange book title, authored by this strange pseudonym, immediately caught my interest because it is so unlike the serious programmers and programming books that I have become familiar with throughout my career. The book doesn’t begin with a forward, with acknowledgements or a table of contents or a summary to sell you on what you’re about to learn.

It begins with comics. Weird comics. “An elf and his pet ham.” Pixel art and old pictures taken out of context and given captions.

When we get to the second chapter (page 2) and some actual text, it apes the format of a “normal” programming book, but continues to be absurd. The opening blurb sells the book by explaining that it will make us cry over the beauty of this programming language. There’s an extremely long sidebar (and dear God, programming books love sidebars), to talk about what the author will “do with the massive proceeds from this book,” which is, in fact, written under an open license that lets anyone do anything they want with it.

The remainder of the chapter is dedicated to a shaggy dog story with a literal shaggy dog, an explanation of how learning the Ruby programming language will make you a better person, and another nonsensical story to explain why the book has cartoon foxes. It’s a pretty accurate introduction to what you’ll be getting in the rest of the book.

The (Poignant) Guide does eventually settle down into some actual code examples and explanations. However, as you get further along, the code seems to be less and less of the book, while the bizarre stories and long-winded sidebars take up more and more of the text.

The truth is that, even if you’re a programmer familiar with other languages, the guide is not actually all that helpful for learning the Ruby programming language. It’s a fever-dream of non-sequiturs, silly stories and comics that happens to include some programming instruction. When I first read it, it inspired me to seek out other resources to learn Ruby, but it wasn’t enough by itself to really get a grasp on the language.

So what was the guide trying to be? Is it a post-modern masterpiece? An allegory? Just some weird stories that a programmer wrote down for fun? Maybe it wants to be a mish-mash of all of these things.

Why the Lucky Stiff

I only learned about _why after the fact.

_why developed many projects in the Ruby language, some larger, some smaller, some popular and some very niche. Over the years, his philosophies became more apparent through his writings, bloggings, twitter and projects.

He didn’t seem to put much stock in the serious programming that is the norm in the industry. He made useful tools, but he also just goofed around a lot in his literary projects and in his code. From writings like The Little Coder’s Predicament, we glimpse his frustration with the pain and complexity of “serious coding” and a desire to get back to basics: just hacking on things because they’re fun and interesting, and not worrying so much about doing it the “right” way.

I do not write tests for my code. I do not write very many comments. I change styles very frequently. And, most of all, I shun the predominant styles of coding because that would go against the very essence of experimentation. In short: all I do is muck around.

A letter from _why

Many people found inspiration in _why’s hacking and in his philosophy. Some were just in it for the cartoon foxes and the ham. And, of course, all the comics and goofy stories and non-sequiturs irritated a lot of people who didn’t get it.

Interestingly, as _why became more well-known, he remained pseudonymous. Even when he spoke at the occasional software conference or showed up to some real-life community event, he went by his online moniker. For the most part, nobody seemed to mind or think too much about it. It was just another fun quirk on top of all the others. But it turned out to maybe be important, because one day, _why disappeared.


_why didn’t just disappear. He removed all the evidence of his existence. He deleted all of his projects, his website, and his Twitter account. There was no warning. Nobody saw it coming.

If he was a somewhat divisive character before this, he became outright controversial in the wake of his disappearance. There were many people who used and relied on his projects, and many who simply felt abandoned by an important parasocial figure.

Whether or not there were more personal reasons for the emotion, most of the community’s anger manifested as irritation that _why had taken down all of his code. Broken and buggy dependencies on other people’s code are a perpetual problem when it comes to software development, and many members of this relatively close-knit community felt betrayed as they were forced to clean up all of _why’s missing projects.

Of course, we know by now that nothing ever disappears completely on the internet, and it turns out that most everything, from his code to his comics to his writings, were preserved in various electronic nooks and crannies. In time, pretty much all of his work was reassembled.

With the projects restored, much of the buzz of the event died down. There were some rumors that _why might have been doxxed, and this was what led to his self-imposed exile from the Ruby community and the internet at large. That still left the question of why he was so worried about remaining pseudonymous in the first place. The mystery of _why’s disappearance still bothered some people, but no clear answers were forthcoming, especially from _why himself.


Three or four years went by. Why the Lucky Stiff became just another interesting anecdote in the vast morass of the internet. People occasionally found his writings (re-hosted by others). People stepped in to take over his projects.

It was a bit of a shock when he returned, and he did so in exactly the sort of bizarre and cryptic fashion that anyone familiar with his work would expect. He left a printer queue that provided a series of hidden messages. The internet, being what it is, immediately took up the puzzle, along with renewed arguments over whether _why should be celebrated or reviled.

The eventual results were nearly a hundred pages—another book, of sorts, which was eventually named CLOSURE. As far as I know, it’s the last thing written by _why.

This feels like the ultimate distillation of the _why aesthetic. It’s not wrapped up in being a programming manual. It’s just a series of strange jottings and stranger stories. But here, clearly, it’s not entirely random and surreal. The text itself makes reference to _why’s disappearance, the opinions of the crowd about him, and itself, wrapping around in a sort of literary ouroboros. It’s clearly allegorical, and sometimes even comes out and says things directly. But it’s also contradictory.

NOW: Lay into the printer queue thing. Just lait on thick with the “4 to 11” just over and over. Try to remember, this is the guy’s only chance to recover from annihilating self-sabotage, okay?

_why – CLOSURE


_why’s writings stand on their own. They’re a fascinating mix of surrealism, silliness, and occasionally deep thoughts. _why is a talented, if eccentric writer. He combines comics, drawings, stories and anecdotes into something cohesive.

However, I think _why is one of those writers that can’t be properly read without understanding some of the context around his writings. Being a programmer certainly helps, but his work, his exile and his return all play into his writings, especially CLOSURE.

We’ll never know exactly what motivated _why, what exactly made him go away, or what he thought about all of this. We only have his writings to go by. I suspect those are more interesting and satisfying than the plain, unvarnished truth. And so does he.

In CLOSURE, _why talks about reading all the works of Kafka, who asked a friend to burn all of his work when he died:

Of course he didn’t want them burned.

This was just Kafka, writing his own death.

This ending has his signature on it.

Reality’s a kind of medium, maybe greater than paper.

Further Reading

Author: Samuel Johnston

Professional software developer, unprofessional writer, and generally interested in almost everything.

2 thoughts on “Great Writing — Why the Lucky Stiff”

  1. What an interesting post. I must admit that I only dabble in programming, so I probably wouldn’t get a lot of what goes on in the book, but that quote about mucking around seems so apt, especially for people who learn programming on their own. It also translates well to writing advice in general. Thanks for this lovely post!

    Liked by 1 person

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