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“Whyday’s” tenth anniversary is Wednesday!

While sorting out the image archives of this blog over the weekend, I noticed this photo:

In case you don’t recognize it, it’s a picture an underappreciated classic of programming literature known as why’s (poignant) guide to Ruby, a book written by the enigmatic programmer and artist who went by the nom de plume of why the lucky stiff.

That’s when it hit me:

Is Whyday still a thing?

And if not, can we make it a thing (or at least capture its spirit) again?

why’s (poignant) guide to Ruby

During the the ’aughts, Ruby exploded from obscure programming language whose best documentation was in Japanese and became the darling tool of startups everywhere. A good chunk of that popularity came from Ruby’s killer app, Rails.

However, at least some of wave of Ruby programmers that appeared at the time has to be credited to _why. Yes, that’s the commonly-accepted short from of his name, and no, the underscore is not a typo. If Rails’ preternaturally handsome creator  David Heinemeier Hansson made Ruby cool, _why, with his “skinnier, edgier Jack Black” appearance and style, made Ruby fun.

While there were a number of books on Ruby at that time, why’s Ruby tutorial, why’s (poignant) guide to Ruby stood out. First, there’s that title. But that was only the beginning.

The book’s first page looked like this:

It featured whimsical recurring characters, such as the cartoon foxes whose catchphrase was “Chunky bacon!”…

…not-quite-sane science adventurers, who, when not dynamiting retirement homes, will teach you the basics of classes and branching…

The “Dr. Cham” chapter features code like this:

And let’s not forget the elf with a pet ham and the cat:

For new programmers, it was an approachable book that didn’t try to bury you with jargon. For experienced developers, it provided a refreshing take on programming concepts. If you were looking for a Ruby reference, you were reading the wrong book. But whether you’d been a programmer for 20 minutes or 20 years, it was a fascinating, engrossing read that made you think about programming differently.

If that wasn’t enough, the book came with its own soundtrack. In addition to being a programmer and illustrator, _why was also a musician with a tendency towards the “indie rock”-style, and he wrote a song for each chapter.

Thankfully, the book and soundtrack preserved online. Go ahead and give it a look. I’ll wait for you here.

_why’s code

In addition to the poignant guide, _why also wrote a fair bit of code, some of which became de facto or even de jure Ruby standards:

  • Hpricot, an HTML parser that became the Ruby de facto standard for a while. The current de facto standard parser, Aaron Patterson’s Nokogiri, was designed to use Hpricot’s syntax.
  • RedCloth, a module for using the Textile markup language in Ruby.
  • Markaby — short for “markup as Ruby — which was a DSL to generate valid HTML using Ruby blocks and methods instead of tags.
  • Camping, a Markaby-based microframework inspired by Rails. Its code amount to less than 4 kilobytes.
  • Hobix, a YAML-based weblog application written in Ruby.
  • MouseHole, a personal web proxy that can rewrite the web à la Greasemonkey
  • Syck, a YAML library for C, Ruby, and several other languages. For a time, Syck was a part of Ruby’s standard libraries. It’s still available as a gem.
  • unHoly, which converted Ruby bytecode to Python bytecode, which made it possible to run your Ruby applications on the Google Application Engine.
  • bloopsaphone, a crossplatform chiptune-like synth, based on PortAudio with a Ruby frontend.

Of his creations, my favorites were the ones that were part of his mission to solve what he called “The Little Coder’s Predicament,” which is that in spite of the fact that we had better computers, software, and networks in the 2000s, the barrier to entry for programming — especially for kids — had become much higher:

In the 1980s, you could look up from your Commodore 64, hours after purchasing it, with a glossy feeling of empowerment, achieved by the pattern of notes spewing from the speaker grille in an endless loop. You were part of the movement to help machines sing! You were a programmer! The Atari 800 people had BASIC. They know what I’m talking about. And the TI-994A guys don’t need to say a word, because the TI could say it for them!


The old machines don’t compare to the desktops of today, or to the consoles of today. But, sadly, current versions of Windows have no immediately accessible programming languages. And what’s a kid going to do with Visual Basic? Build a modal dialog? Forget coding for XBox. Requires registration in the XBox Developer Program. Otherwise, you gotta crack the sucker open. GameCube? GameBoy? Playstation 2?

His solution to the Predicament was to first write Shoes, a simple toolkit for Ruby that use web page concepts to build desktop GUI apps for macOS, Windows, and Linux:

Shoes formed the basis of Hackety Hack, an IDE combined with a tutorials system that was a lot of fun to use. Here’s a screenshot of Hackery Hack in action, being used to write a “Hello, World!” program:

Since _why was developing this tool for children, he went straight to the subject matter experts: 25 children and their parents, whom he consulted and used as testers as he worked on the project.

(And because this was a _why project, it had a manifesto. Read it; it’s good.)

Here’s the Hackery Hack site:

_why’s performances

I was at RailsConf 2006, where _why gave a multimedia extravaganza of an evening keynote presentation. It was something I’d never seen before or since at a keynote: Part programming lecture, part video show, part concert complete with his band, the Thirsty Cups. You either left this performance either scratching your head or wanting to take programming to strange new heights.

After the show, I had a chance to hang out in an unexpected gathering of people that included both _why and Martin Fowler, which was an amusing, enlightening, and amazing experience.

_why’s disappearance

As you were reading this article, you may have noticed that I have only referred to its subject as “why the lucky stiff” or “_why”.

You may have wondered — quite fittingly — why?

There’s no definitive answer, but there are some hints.

Like a lot of creatives, the person behind the “why the lucky stiff” persona is an intensely private person. _why could be the out-there guy performing songs about how Ruby’s error handling just sounded so much more capable and effective with its rescue statement versus other languages’ try and catch (“try to catch me, I’m falling!” he’d joke), but the person lurking behind the mask wanted privacy during his downtime.

_why made it a point to reveal as little about himself as possible, and most of us were happy to indulge him. Most people were happy to simply know and address him as “why”, and in the community, it was a point of etiquette to not try and dig too deeply.

Of course, even in those pre-GamerGate, pre-“shitposting”, pre-chan-ruining-lots-of-the-net times, _why’s secrecy didn’t sit well with some people, who for some reason, just had to know the name of the person behind the _why identity was. So in 2009, they dug deep, and eventually found his name (as well as his wife’s) and publicized it.

_why may have also been a victim of Open Source Success, when a little project that you worked on in order to scratch a creative itch becomes so popular that many other projects depend on it. Suddenly, your project is no longer just a little thing you worked on, but a big thing that people expect you to maintain and upgrade. I’m reminded of a line from Byrne Hobart’s article, Working in Public and the Economics of Free, and it’s simultaneously hilarious and sad:

Running a successful open source project is just Good Will Hunting in reverse, where you start out as a respected genius and end up being a janitor who gets into fights.

As a result of the factors listed above, plus some others probably known to no one else but _why, the internet presence of Why the Lucky Stiff vanished on August 19, 2009. His sites, blogs, social media, and code repositories all vanished. I wrote about it the day after it happened.

Luckily for us, all of his work — well, the work that he’d released to the public, anyway — was open source, and with the effort of some dedicated Ruby and Rails developers, his projects were saved. Some people even took them over and expanded on them. Other projects became the basis of newer, improved projects.


In 2010, a year after _why vanished into the night, Glenn Vandenburg declared that August 19 should be celebrated as Whyday.

Here’s what he wrote on the Whyday site:

On August 19, 2009, Why the Lucky Stiff withdrew from the online community. We in the Ruby community wish him well, but we really miss him.


Why gave us a lot of cool software and other things, but what he really gave to the Ruby community was a spirit of freedom, whimsy, and creativity. When Why took the stage at the first RailsConf, in 2006, he strapped on his guitar, walked to the microphone, and yelled “Put your best practices away!”


Discipline, care, and responsibility are important; we owe our customers, employers, team members, and families to take our work seriously. At the same time, though, we need to play. If we don’t occasionally break out of the mold of our “best practices,” we can easily miss many wonderful ideas, some of which can bear rich fruit (just as Camping and Hpricot led to Sinatra and Nokogiri).

On Whyday, we’re encouraged to borrow a page from _why’s book and creative, instructive, collaborative, and crazy. The site suggested doing things such as:

  • See how far you can push some weird corner of Ruby (or some other language).
  • Choose a tight constraint (for example, 4 kilobytes of source code) and see what you can do with it.
  • Try that wild idea you’ve been sitting on because it’s too crazy.
  • You can work to maintain some of the software Why left us (although Why is more about creating beautiful new things than polishing old things).
  • On the other hand, Why is passionate about teaching programming to children. So improvements to Hackety Hack would be welcome.
  • Or take direct action along those lines, and teach Ruby to a child.

The Whyday site lives on, but it’s been a while since I’ve seen anyone make a fuss about Whyday.

I thought that given that we’re in the middle of a pandemic and that we’re all spending more time at home (at least I hope we are), there’s no better time that now to bring back the spirit of Whyday.

This Whyday, I plan to celebrate by starting some kind of creative project. (Actually, I plan to start a couple.) If you can, you should start one, too! 

Recommended reading and viewing

Got eighteen and a half minutes? Then you’ll want to watch this documentary on Why the Lucky Stiff and how he inspired the Ruby developer community:

Articles on _why:

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