Whyday is Friday

Photo of why the lucky stiff's book 'Why's (Poignant) Guide to Ruby' in hardvoer form, backed by paper cutouts of why's cartoon characters.

Clever programmer. Multimedia and performance artist. Whimsical writer. Oddball performer. Howard Hughes-style recluse. All of these phrases are apt descriptions of the guy most of us know only as why the lucky stiff, or _why for short.

Bold, Brief and Gone

'Cartoon foxes' comic from why's (poignant) guide to Ruby

If _why had a personal motto, it might be “Be bold, be brief, be gone.” The bold part was plain to see. His Ruby tutorial, why’s (poignant) guide to Ruby, broke away from the style of your typical programming books and went for the wild and whimsical. Only _why would take a topic like metaprogramming — something that confounds a number of experienced developers, never mind the newbies he was trying to reach in his book — and turn it into a fantastic adventure game exercise, complete with comics. Few developers have the breadth of skill and interest to make projects like Try Ruby (a browser-based Ruby shell with instructional guides) to Camping (a Rails-like web app microframework smaller than 4K) to Shoes and Hackety Hack (a UI toolkit for “web-like desktop apps” and a development environment to teach children programming) to Park Place (a “nearly complete clone” of Amazon’s S3). There may be people out there who’d be able to pull off a music-and-programming performance like the one he did at the first RailsConf, but they haven’t yet presented themselves to the world.

Why non conformist certificate

The “brief” and “gone” bits take a little more explaining. _why’s notoriety rose with Ruby’s popularity, which in turn was connected to Ruby on Rails. I remember reading some posts on one of his blogs, RedHanded, as far back as late 2003, and the (poignant) guide surfaced in 2004 and found its way into print in 2005, when the chapter A Quick (and Hopefully Painless) Ride Through Ruby (with Cartoon Foxes) appeared in the Apress book The Best Software Writing I: Selected and Introduced by Joel Spolsky. His music-and-code extravanganzas at South by Southwest, O’Reilly’s Open Source conference and the first RailsConf cemented his rep as the programmer who was also a performance artist and by 2008, people were seeking him out for all sorts of things, from personal appearances (Pete Forde tried to get him to come to RubyFringe, but convincing him to leave the US proved to be impossible) to commissioning body art (Leah Culver got him to design a tattoo for her).

Leah Culver shows off her tattoo by why the lucky stiff

Close-up of Leah Culver's tattoo by why the lucky stiff

All in all, _why’s popular presence on the web spans about 5 or 6 years.

Milk carton with drawing of _why in the 'missing child' picture

For reasons still unknown to the Ruby community at large — perhaps Matz knows and is sworn to secrecy — _why “disappeared” on August 19, 2009. It’s not that he disappeared in the D.B. Cooper sense, but in the J.D. Salinger sense: not as a legal missing person, but as a person determined to remove himself and his activities from the public eye. In the span of a day, he removed as many traces of his online presence as he could: the blogs, the sites, the projects. Luckily, there’s a lot of his work floating around thanks to his open sourcing and Creative Commons-ing of his works and the curation of many techies who appreciated them.

WhyDay Declared


A year after his disappearance from the online world, Glenn Vandenburg declared the first anniversary of his disappearance as “Whyday”. Whyday is a day to celebrate _why’s contributions to the culture and communities that have grown around the Ruby programming language and all the software built upon it. “We in the Ruby community wish him well,” goes the text on the Whyday site, “but we really miss him.”

A spread from 'Nobody Knows Shoes, the documentation for Shoes, _why's UI toolkit for desktop apps

The Whyday site goes on:

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).

This year, on August 19, celebrate Whyday. Set aside that day to remember Why’s contributions to our community and culture by hacking just for the fun and joy of it.

Why the lucky stiff and the Thirsty Cups playing at SxSW

Among the things people were encouraged to do on Whyday were:

  • 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.

I made a note of WhyDay on my personal tech blog, Global Nerdy, as well as the blog I got paid to write for (I was a Microsoft employee at the time). I didn’t get the chance to do as much as I’d like in the spirit of Whyday, probably because I was knee deep in getting ready for TechDays, a series of cross-country conferences run by The Empire.

WhyDay 2011

Youre leaving us here

Here we are, a year after the first Whyday. I’ve done some quick searching and haven’t found any mention of celebrating Whyday this year, so I’ve taken it upon myself to spread the word. It probably helps that I’m no longer at Microsoft and now in Shopify, which not only builds stuff on Ruby and Rails; it was also co-founded by an original member of the Rails core team, and people here are writing the next edition of Rails in a Nutshell. This place just oozes Ruby.

_why might not want to be celebrated, but in my mind, _why isn’t the real reason that Whyday should be celebrated anyway. I think it’s more about the spirit of what _why did: really getting to know the tools you’re using, helping people understand those tools using unorthodox means whenever conventional means just don’t get the point across, and building great tools when the tools you want don’t exist.

It’s about finding joy and delight in your craft, and bringing to it a sense of play. It’s about making things better. All that is in the spirit of why I quit a high-paying, cushy job and joined a rag-tag team of techies in a startup, and this year, I’m going to try to celebrate Whyday — this Friday, August 19th, 2011, a little more properly.

How about you?

Last page

This article also appears in the Shopify Technology Blog.


“Get Excited and Make Things”

As a Developer Evangelist, it’s my job to make sure that programmers are inspired to build software. In the pursuit of that goal, I’ve the picture below as the last slide in my presentations at TechDays and Career Demo Camp. I’ve had a number of requests for the image, so I’m sharing it below:

Poster: "Get Excited and Make Things"Click the image to see it at full size.

The poster is Matt Jones’ reworking of this poster issued by the British government during World War II during “The Blitz”:

Keep calm and carry onClick the image to see it at full size.

Enjoy the pictures and remember: Get excited and make things!

(And if you do make things, let me know! I’d love to feature you and your work in this blog.)

This article also appears in Canadian Developer Connection.


Hugh MacLeod at Startup Empire: We’re So F***ed


startup_empireThe second-last speaker at yesterday’s Startup Empire conference was Hugh MacLeod, whom most of us know for his comics drawn on the back of business cards and his blog, Gaping Void. Here are my notes from his presentation:


  • It’s easy for an advertising career to tank, especially if you live in New York and drink too much
  • I started drawing comics at bars, on the paper that just happened to conveniently be around: the backs of business cards
  • I’m not in the VC business, nor am I in the tech business
  • I’m greedy — who here’s greedy? [Many hands go up]
  • What really drives us? The "C" word: creativity
  • The reason we work in this field is that we want to build stuff — fun stuff
  • If it pays the bills, so much the better
  • The "we’re so fucked" thing is pretty long term
  • What will get us out of the hole? Creativity. People like yourself, doing and building cool things
  • I’m in my 40s — what motivates me now is seeing bright ambitious kids coming out of the colleges
  • When I was a kid, there was no internet — not even computers! I had to write my term papers on typewriters
  • I want to talk about creativity to the young
  • I now present 12 little tips for you people just getting started


1. Ignore everybody.

  • When you come up with a really great idea and show it, people won’t get it
  • You yourself might not even get it
  • Imagine the early days of search: “Why would you want to do that?”
  • “Good ideas have lonely childhoods”
  • If you’ve had a good idea, you were probably called a fruitcake at the start
  • Good ideas alter power balances in relationships, which is why many people resist them
  • Your boss doesn’t want you to have a good idea that makes you richer than him
  • Good ideas will meet resistance – not because of the idea, but because of power and hierarchy

2. The idea you have doesn’t have to be that big.

  • Jewish proverb: “A rich man is one who can satisfy his wants”
  • I grew up on TV, watching shows about people who had more than us
  • Fast-forward 20 years later, I get to do what I want every day:
    • Haven’t had to set my alarm clock in years
    • Just me and a couple of pens
  • And yeah, I read Fast Company, BusinessWeek — “business porn magazines” – they feed greed
  • Anyone seen No Country for Old Men? I live in that town!
  • One of the locals is Harry, the master brewer, who moved out there and opened his own bar. He makes $500 a day and is the best businessman I know. He does what he wants and everything he does has some meaning to him.
  • Meaning scales!
  • We owe it to the generations to come to find meaning


3. Put the hours in.

  • Nothing happens overnight
  • People look at what I do "Aren’t you worried about people ripping you off?" or taking my idea and doing the same thing
  • My response: "I’ve already done 10000 cartoons and 7 years blogging"
  • Inertia stops a lot of people. Know anyone in a dead-end job? Ever been in one? They say "One day, I’m going to open that cheese shop. But right now, I have to write a report…"
  • I have a book coming up. Didn’t quit my job to write it; just woke up an hour earlier every day to write it and posted it on my blog. Penguin eventually contacted me. All I did was put the hours in.


4. If your business plan relies on you being discovered by a big-shot, you will fail.

  • I once got a book contract offer. The terms in the contract were terrible and I turned it down
  • The publisher, it turned out, was in the business of finding people so desperate to have their moment in the spotlight that they would sign anything
  • We now live in an era of cheap, easy, global media — we don’t need middlemen
  • I’m friends with Rick Segal…but probably because I don’t need venture capital!
  • Where I live in Texas, you can live really cheaply. Part of this is because you run out of things to spend on
  • When I hear about people talking about VCs, I think of people looking to have their sorry asses saved
  • Don’t get me wrong: it’s great to have VC, but it’s even easier when you get one because you don’t really need one
  • "If you’re looking for advice, ask for money; if you’re looking for money, ask for advice.”

5. Do it anyway.

  • You don’t know that your idea is the right one at the right time – no one does!
  • Do it anyway — that’s how great ideas start out
  • Seco0nd-rate ideas are all about the immediate "yes!" response because it keeps them alive longer


6. Everybody is born creative.

  • “Everybody gets a box of crayons when they’re young .”
  • We turn adolescent and for many of us, somehoe, “our colour gets turned off”
  • Suddenly, it’s not about coloring anymore, but concerns like “Got to get a 3.5 GPA, got to get that job…”
  • Then you get an idea that you can’t turn off
  • It makes you start avoiding your poker buddies
  • Most people get scared off by that idea. Doubt creeps in: "What if I get a bad publisher? What if nobody likes my idea?"
  • That’s not your idea, that’s your grown up boring self fighting that idea
  • Your idea came to you because your soul needs it
  • If you don’t nurture that idea, it dies. It also takes a lot of you with it.

7. The “Sex and Cash” theory.

  • If you have a creative life and you make money doing it: you generally bounce between two kinds of jobs:
    1. The sexy creative job
    2. The one that pays the bills
  • In movie stars’ cases, that means alternating between parts in popular hit movies and critically-acclaimed art films
  • For a photographer, that means alternating between doing work for indie art mages and paying the bills with photo shoots for catalogs
  • Consider Martin Amis: he writes critically acclaimed novels and supplements his income by teaching courses and writing newspaper and magazine articles
  • As for me: I do comics on the back of business cards, and I do work for Microsoft and Dell
  • It’s a balance of artistic sovereignty and making a living
  • “The moment you accept this is when you take off .”


8. Remain frugal.

  • This particular lesson took me the longest to learn
  • Living in New York City, I was in the top income bracket, for all the good it did. I had so much outgoing cash in rent and other expenses.
  • You can live like a king where I do, in Alpine, Texas quite cheaply
  • I now have “West Texas expenses, New York wages”
  • This is hard to do if you want to be seen in “all the right places”
  • Remember: we become creatives because we want freedom, and that includes freedom from avarice

9. I’m going to skip this one.

  • It’s too corny!
  • [He capitulated later; see the end of this article.]

10. The more talented somebody is, the less they need props.

  • At any advertising agency, it’s always the second-rate art director who’s the first to get the newest model Mac
  • If you go to any magazine office, it’s the second-rate writer keeps an old Remington typewriter on display
  • You see this at startups too: the loft office in the hip neighbourhood with the foosball table
  • Remember: the Gettyburg address was written on borrowed stationery!
  • We use props to hide behind or mask our inadequacies
  • I know a woman who recently IPO’d — she didn’t start in a fancy office, but on her dining room table
  • It’s not the props, it’s the good idea and the effort

11. The best way is not to stand out from the crowd, but avoid the crowd altogether.

  • Bartenders are the great social enablers of New York City
  • No under-50 bartender is really a bartender: they’re actors, musicians, whatever
  • They have plan to become famous photographers, musicians, whatever
  • The thing about the arts to me: what often drives people isn’t just the money or business, but the prestige: “I want to be like that guy, because he’s really privileged”.
  • Ever noticed how few really good writers have blogs? You don’t see literature, you see shit like what I write
  • A lot of authors are enamored of books and the prestige attached to them
  • The worst thing you can do as a creative is fall in love with a privilege model

12. If you can accept the pain, it cannot hurt you.

  • When my sister was born and my mom was in labour, the pain was unbearable — "Why is this happening to me?" she asked
  • The midwife replied: "You’re giving birth to a baby. It’s supposed to be painful."
  • Mom accepted that and got on with the birth
  • Trying to do something worthwhile and creative is really hard
  • As you get older, you realize that pain is part of the process


9. Okay, here’s point number 9, since you asked: We will fail, but we will be forgiven.

  • Failure is part of the process
  • The important thing really isn’t about reaching the summit, but setting out for it.


“why the lucky stiff” on Why You Should Create

Why\'s photo-illustration of his book, \"why\'s (Poignant) Guide to Ruby\"
why’s (Poignant) Guide to Ruby, the most whimsical programming book ever written.

Here’s a great quote from the enigmatic programmer known only as “why the lucky stiff” on why you should create:

when you don’t create things, you become defined by your tastes rather than ability. your tastes only narrow & exclude people. so create.

Very true, especially since there are whole industries and professions that specialize in manipulating your tastes in order to get you to line other people’s pockets. Well put, why!


Why you shouldn’t listen to “hasn’t someone done that already?”

Why shouldn’t listen to “hasn’t someone done that already?”: Because doing something that someone else has done, just better, can work. Ray Grieselhuber lists 19 success stories that did just that.