It Happened to Me Work

11 Months as a Microsoft Man


While Kris Krug was taking photos of me for TechDays, his assistant Danielle was holding up a light reflector and remarking that I seemed to really love my job. I hadn’t yet told her that I really loved my job; I was just doing my thing, running my track of the conference, chatting up the attendees and missing most of the lunch break to play accordion and pose for a photo shoot. I’d been up since before sunrise on the morning of the first day of the first of seven conferences where I’m acting as track lead for the first time and she knew it – it’s hard to fake enthusiasm under those circumstances. I was “on” because I love my job.

As I write this — September 20th — it’s been exactly eleven months since my first day as a Developer Evangelist for Microsoft. I suppose I could have waited another month for the traditional anniversary to talk about my time with The Empire, and were I a little less enthusiastic about my job, I probably would have done just that. But I can’t wait, so why bother?

Inspirational poster: 'Unemployment: Sucks when your job gets blow'd up.' with sad stormtropper sitting on a subway train.

It hasn’t even been a year since I got laid off from my last job: that anniversary doesn’t happen until September 24th – this Thursday. The insult-added-to-injury of getting laid off on my own wedding anniversary (they didn’t know, but the layoff was still worse for it) makes the event a little more memorable. It also gave me the choice of viewing the days to follow as a trial or an adventure. You already know which one I chose.

Thanks to the help and referrals of a lot of a readers of both The Adventures of Accordion Guy in the 21st Century and Global Nerdy, I had a job interview or job-search-related meeting on nearly every day of the three weeks between my getting laid off and my signing the offer letter from Microsoft. These meetings were all quite different: I had a great interview with a great small company, an interview with a company that I thought would be great but turned out to be scatterbrained, and even an interview with a company I expected to be a Mickey Mouse outfit but turned out to have surprising depth. I also had interviews with Microsoft: six of them, in fact.

I'm a Mac, I'm UNIX, I'm Vista poster

I have to admit that I had some concerns about joining The Empire. After all, for the previous 6 years, I’d been using Python and PHP, and then working my way into becoming a Rubyist. I used open source tools to write software and either Mac OS X or Ubuntu in my day to day work. I was deep in the culture and the scene of the “I work on a Mac and deploy onto Linux” crowd. Could I work for Microsoft? And could I work in an office park out in the burbs?

(The last time I interviewed for a job in an office park in the burbs, this happened.)

You already know the answer, but you might not know the reasoning behind the answer. “It’s the money!” is everyone’s first guess, and it’s a good one – just not the right one. Yes, a company like Microsoft would be able to give its workers decent salaries. It certainly played a factor in my decision, but a couple of the other potential jobs were offering roughly the same number of ducats. However, if money were the primary factor in my career choices, I’d have gone for one of the programming jobs at a bank or insurance company that were available to me right out of school instead of starting at $12.50 an hour at a CD-ROM company run by art school grads. But I suspect that you wouldn’t be reading this blog – probably because I’d be neck deep in a mid-life crisis.


For starters, the job isn’t out in the burbs. In fact, I haven’t worked in a situation as flexible as this one since I was a self-employed consultant. The field people in Microsoft’s Developer and Platform Evangelism (DPE) team are classified as mobile workers and most work out of their home offices, with occasional visits to the office for meetings. I split my time between the home office, cafes (where I’m surprisingly productive), the Hacklab (a “hackerspace” in Kensington Market to which I have 24/7 access) and the Microsoft office out in the burbs, where I show up to gain access to the most important network: not the corporate one, but face-to-face contact with my non-remote coworkers in various departments.


Another perk of the job: considerably more control over my own destiny than one might expect. A Microsoft evangelist’s role is pretty broadly defined, specifying the what of what we do. The how part is defined in our commitments, a document where each of us writes how we’ll fulfill our role, on both an individual and team level and then gets agreed upon with our managers. I happen to report to John Oxley, an exceptionally understanding manager, so when I threw away the suggested “hows”, wrote my own from scratch and set a couple of rather ambitious goals, he approved them.


I wouldn’t have joined Microsoft had I not seen the signs of some course corrections, the cumulative effect of which I like to refer to as “The Sea Change”. There are lots of factors, including an increasing willingness to “play well with others” – embracing standards, an emphasis on interoperability, participation in community events, the hires of unlikely people including my friend David Crow, and a lot of good tech, ranging from great developer tools to platforms like Silverlight and XNA, to the then-upcoming technologies like “Red Dog” (which became Azure) and ASP.NET MVC (still in beta back then) to the fact that they were starting to look at what an open source approach could do for them. Yes, the company still is a bit hung up on desktop computing and its old  approaches – it’s hard to walk away from the goose the laid the golden egg for two decades – but there are signs that change is afoot.


Finally, there’s the challenge. Evangelizing at Microsoft means reaching out to a larger body of developers and techies than I ever could anywhere else, working with a platform than spans embedded systems to high-performance machines to data centers spread throughout the world – and doing so for a company facing the challenges of its size, its competitors and its own past.

To put it a little more simply: Any fool can evangelize Apple or Google. It takes a rock star, ninja and Jedi master all rolled into one to be an evangelist for Microsoft. It’s not that there’s nothing from Microsoft to evangelize – it’s just that there are lot of factors that make the job something that not just anyone can do.

I view my job as so much more than winning techies’ hearts and minds on behalf of The Empire. It’s about making big changes: changing the company, the culture of high tech, the field of software development and yes, the world. It’s a bold, audacious, chutzpah-riffic set of goals and it won’t be easy – but the most rewarding work rarely is.


So here I am, eleven months later. The work has been exciting, rewarding and challenging. I believe I’d started to make my mark on the company and hopefully someday, the industry. Every day, I get the opportunity to do the things I love to do: write code, talk to people and come up with new ideas, often in the surroundings of my choosing. I feel like equal parts Don Draper and Don Box!

It’s been great so far. I’m going stick around for a little while.

I can’t close this article without a few thank-yous:

  • To my manager John Oxley, for hiring me, trusting that I would temper my wacky ideas with solid judgement, giving me the freedom to operate in the way that lets me work my magic and for making sure the higher-ups were aware of my work.
  • To David Crow, for being one of the guys to recommend to DPE that they hire me as soon as he heard I’d been laid off.
  • To my fellow Developer Evangelist John Bristowe, for mentoring me through my freshman year at Microsoft and for being the other guy to recommend to DPE that they hire me.
  • To my former VP Mark Relph, for his support.
  • To the rest of my team, who are too numerous to name, but whom I hold in the highest esteem.
  • To the other groups within The Empire with whom I work: CSI/Interoperability, Windows Phone, Open Source and our event organizers Maritz – I hope to keep on working with you folks!

This article also appears in Global Nerdy.


Microsoft Canada Wants to Pick Your Brain!

Zombie picture: "I can has brains?"

If you’re a developer or IT Pro based in Canada, my team at Microsoft Canada – the Technical Audience Team – would like to pick your brain in order to find out how to better serve you. The full details are in my tech blog, Global Nerdy.

Geek It Happened to Me Work

Mental Models, Mantras and My Mission

This article also appears in Global Nerdy. Like the previous article, it’s about my role at Microsoft and doesn’t delve too deeply into technology, so I thought it was suitable for a more general audience and decided to republish it here. Enjoy!

Mental Models and Bill Buxton’s “Draw a Computer” Exercise

Bill Buxton

In the mid 1990s, well before he was Microsoft’s user interface guru, Bill Buxton often asked people to carry out a simple little exercise: draw a picture of a computer. Most, if not all, of the people he asked would draw something that fit the common mental model of the desktop computer of the era: cathode ray tube-type monitor, keyboard, mouse and that box housing the motherboard and drives that many people mistakenly refer to as “the CPU”.

If Buxton were to ask the question today, the drawings of computers might look like these:

Four computers from the 2000s - a laptop, a couple of all-in-one-desktops and a desktop with a "box" -- all with flat screens

If he asked the question in the mid-to-late 1980s, the drawings might’ve looked like these:

80s-era computers: Apple ][, Commodore 64, TRS-80 and IBM PC

And had he asked the question in the mid-60s, the drawings might’ve looked like this:

The classic fake "home computer as envisioned by RAND" photo

Buxton likes to point out that the changes in computers from the 60s onwards are largely in the implementation technology, processing power and outward appearance. When most people draw computers, he said, they’re merely drawing their mental model, which is based on the outer packaging.

However, if you use the mental model of a technologist, computers have been essentially the same instruction/ALU/storage/input-output boxes whether they’ve occupied whole rooms or fit in your pocket. They’ve been pretty much the same at their core, in the same way that fancy tech and hybrid engine aside, there really isn’t too much that separates a present-day Toyota Prius from a Model T Ford.

If Bill Buxton could approach Microsoft Corporation as a person — and hey, that’s the way the law treats corporations, so why not? – and asked him/her to draw a computer, I suspect that s/he would draw something based on mental model of a souped-up circa 2000 computer: a desktop computer with a nice flatscreen monitor, running Windows XP and having a somewhat limited connection to the ‘net.

I think that this is a problem. I also think that the source of this problem is Microsoft’s success.

Microsoft’s Company Mantras

“A PC on every desk and in every home” was Microsoft’s longest-lived slogan and the company mantra for the first 24 years of existence. Like the best slogans, it succinctly summarized the company’s goal. The problem is that the goal has pretty much been reached. In most parts of the first world, a good chunk of the second world and even a sizeable fraction of the third world, you can easily find a desktop computer, and it’s quite likely that it’s running some sort of Microsoft software.

Since 1999, the company mantra – I really hesitate the use the phrase “vision statement” — has been a little more vague. The company’s been thrashing between them a little more frequently, as you can see in this list of mantras taken from chapter 1 of How We Test Software at Microsoft:

  • 1975 – 1999: “A PC on every desk and in every home.”
  • 1999 – 2002: “Empowering people through great software – any time, any place and on any device.”
  • 2002 – 2008: “To enable people and businesses throughout the world to realize their full potential.”
  • 2008 – present: “Create experiences that combine the magic of software with the power of internet services across the world of devices.”

The post-1999 mantra all seem a little limp in comparison to the original. Reading them, I cannot help but think of a quote attributed to web design guru Jeffrey Zeldman:

"…provide value added solutions" is not a mission. "Destroy All Monsters." That is a fucking mission statement.

Because the old mantra lasted for so long and the new mantras just don’t have the same straightforwardness and gravitas (How We test Sofware at Microsoft quotes Ballmer as saying that we may never again have a clear statement like the original to guide the company), the original remains quite firmly etched in the company culture and mindset.

I think it’s holding us back.

The Desktop as the Goose That Laid the Golden Egg

Altair 8800 computer on display at Microsoft's Building 92 gallery

The original mantra doesn’t just focus on the desktop, it actually mentions it by name. In 1975, when computers were room-filling behemoths that you could access either via batch or time-share, the concept of a desktop computer was downright radical. If you think the iPhone is impressive (and yes, it is), imagine how mind-blowing the Altair 8800, the first commercially-available desktop computer, must have been to a geek back in the Bad Old Days. It was the platform on which Microsoft’s first product – a little programming language called Altair BASIC – was launched, and it was BASIC that in turn launched the company.

In his book Outliers, Malcolm Gladwell talks about how the Altair 8800 was a golden opportunity for Bill Gates and his buddies at his fledgling company, then called “Micro-Soft”. Unlike a lot of other companies at the time, they took the desktop computer seriously. Even when IBM got into the desktop computer game in 1981, it was a product of their Entry-Level Systems division, a clear indication that they thought the PC was a machine you bought until you were ready to graduate to a real computer. I don’t think that this philosophy ended up serving them well.

An Applesoft BASIC cassette featuring a sticker that says "Copyright Microsoft, 1977"

Since the big boys were paying no mind to the desktop computer, upstarts like Microsoft had a big empty field in which to play, and they thrived. Crack open just about any late 70s/early 80s computer that had BASIC built in – even Apple machines — and you’ll see a row of ROM chips with a Microsoft copyright notice. It was Microsoft that swooped in with PC-DOS when a deal with Digital Research for a PC version of CP/M was slow in coming (and this is despite the fact that Gates recommended that IBM go to Digital for an OS). A lot of people’s experience with desktop computers (and Microsoft revenue) is defined by circa-1995 Microsoft thanks to Windows 95 and the results of Bill Gates’ memo titled The Internet Tidal Wave, both of whose influences are still felt to this day.

Once upon a time, it used to be unusual to walk into someone’s home or office and see a computer. These days, it’s unusual to walk into someone’s home or office and not see a computer, and Microsoft’s focus on the desktop had a lot to do with that.

The Desktop as Albatross

Albatross, shot with a sucker-dart arrow, falls on the head of a Disney-esque cartoon character

When electric motors first became available, engineers envisioned factories and eventually houses being equipped with a single electric motor. They imagined that the central motor would, through a series of gears and drive belts, be connected to whatever machines in the house or factory had to be driven by it. What happened in the end is that rather than relying on some central motor, electric motors “disappeared” into the devices that used them. Here’s an exercise to try: go and count the electric motors in your house or apartment right now. The number should be a couple dozen, and if you can’t find them, this article might help.

When big, room-filling computers first became available, engineers envisioned businesses being equipped with a single computer in a manner roughly analogous to the aforementioned big central motor. We know what happened in the end – while many businesses do make use of big datacenters, a lot of the computing power got spread out into desktop computers.

I have a theory that comes in two parts:

  1. Just as electrical motors disappeared into the devices that needed their work, and just as computing power got spread out from big mainframes into desktop machines, computing power is now both disappearing and spreading out into mobile devices and the web/cloud.
  2. Microsoft, with its desktop-centric approach, at least outwardly appears to be missing out on this migration of computing power.

Most of the company’s attention, at least to an outside observer, seems to be focused on Windows 7. Yes, chances are that with computer sales being what they are, Windows 7 will probably end up on more of laptops and netbooks than desktops, but I consider those devices to simply be the desktop computer in a more portable form. It worries me that there have been more concrete announcements about Windows 7 on netbooks than upcoming versions of Windows Mobile, despite the iPhone and BlackBerry-driven evidence that the real mobile action is in smartphones.

(Tomorrow, I’ll post an article in which I argue that netbooks are a dangerous red herring pulling away our attention from devices like smartphones.)

Microsoft ASP.NET

Even when the company reaches out beyond desktop development, there’s no escaping the desktop “gravity well”. Consider ASP.NET (that is, the “traditional” ASP.NET, not the recently-released ASP.NET MVC). To my mind, as well as the minds of a lot of other web developers, it’s a web framework that tries really hard to pretend that the web doesn’t exist. It makes use of a whole lot of tomfoolery like ViewState to create a veneer of desktop app-like statefulness over the inherently stateless nature of the web and a programming model that tries to mimic the way you’d write a desktop application. It’s almost as if it were designed with the mantra “the web is like the desktop, but lamer” instead of “the web is like the desktop, but everywhere”. Although the framework works just fine and there are a number of great sites and web apps built on it, I think a lot of developers sensed this design philosophy and went elsewhere for web development.

(An aside: My old boss at OpenCola in late 2001 told me that he’d been meeting with Microsoft people and suspected that Internet Explorer 6 would be the final version of their browser. The expectation that web pages and web applications would be replaced by Windows client applications pushed over the net, a prediction similar to one made by the Java folks a few years prior.)

Windows Mobile logo

The same situation exists with Windows Mobile’s current user interface, which is basically a subset of Windows’ standard UI controls for the desktop, scaled down to fit smaller screens, and with a stylus standing in for the mouse. It’s almost as if it were designed with the mantra “mobile computing is like desktop computing, but lamer” instead of “mobile computing is like a mobile phone plus PDA and an MP3 player, but cooler.” If the ASP.NET design mantra is a whisper, the Windows Mobile mantra is a scream.

I suspect that the reason the XBox 360 didn’t fall into a similar kind of trap — “set-top boxes are like desktop computers, but lamer and only for games” – is that the XBox team is situated off the Microsoft Campus and less susceptible to the desktop influence.

My Mission

Stick figure, chained to desk, breaking the chain

At my most recent one-on-one meeting with my manager John Oxley, we talked about a need for each member of our Evangelism team to define his or her area of focus. The Microsoft platform is a vast, nerdy expanse spanning the range from embedded computing all the way to Cray supercomputers; no single person can hope to cover it all.

He already had a good idea of what I wanted to focus on, and by now, I guess you do as well. I feel that just as computing expanded beyond the big computer rooms and onto our desktops, computing is expanding beyond our desktops into all sorts of different places:

  • Invisibly, into the web and cloud in the form of web applications and services
  • Visibly, into our pockets and living rooms, and embedded into all sorts of real-world things

While I believe that Windows 7 is a necessary part of the Microsoft platform, I’m not too worried about focusing on it – there are more than enough people at the company to promote and evangelize it. I want to focus on the platforms that I feel that Microsoft hasn’t given enough love and attention: the non-desktop platforms of the web, mobile and gaming, as well where they intersect.

It’s a big area to cover, but I think Microsoft needs to be active in this area if it wants to be true to its forward-looking roots. I even have a mantra for it: “To help web, mobile and game developers using Microsoft tools go from zero to awesome in 60 minutes.” I want to give developers both that rush when getting started with a new technology as well as the sustained passion to keep working with it, in the same way that Ruby on Rails and the iPhone got developers with an initial flash of excitement and turned it into long-term passion. It’s an ambitious, audacious mission, but no more so than the one coined by a bunch of scruffy nerds in New Mexico in the the 1970s: “A PC on every desk and in every home.”

Joey deVilla with cardboard cutouts of Microsoft's 1978 team

Geek It Happened to Me Work

Evangelist, Immigrant and Shaman

This article also appears in Global Nerdy. I thought it might be of interest not just to geeks, but also to people who are thinking about defining their roles at work.

This week, Microsoft Canada’s Developer and Platform Evangelism team is getting together to do its planning for the upcoming financial year, which runs from July to June in The Empire. There’s a lot to talk about, especially in a year that combines the Credit Crunch, the releases of new versions of Windows, Windows Mobile, Visual Studio and who-knows-what-else and a company looking to establish its place in an increasingly web- ad mobile-driven world.

A good place to start might be to think about the roles that we, as individual members of the Evangelism team, play.


Old colorized photo of a boy evangelist with the title "I've got a message!"

Unlike Anil Dash and Jeff Atwood, I never had any reservations about the job title “Evangelist”. The religious connotations never bothered me. It might have had something to do with spending eight years in a Catholic school — it didn’t do me any harm, and it didn’t seem to hurt Keanu, who went to the same school around the same time. It might also have something to do with the fact that like Atwood, I think that “Software development is a religion, and any programmer worth his or her salt is the scarred veteran of a thousand religious wars.” I could never be happy with only programming; I need to mix it with sharing the knowledge and passion for the craft through writing, speaking, schmoozing, performing and entertaining.

Like evangelism of the religious kind, being a technical evangelist isn’t a job that you can do “on autopilot”. There are some jobs that you can do and even excel even though you hate them and the work is of no interest to you. No doubt you’ve seen or know people who do their jobs “on autopilot”, functioning well enough to perform the tasks required of them. Evangelism isn’t one of them. As the title implies, if you don’t have the believe in what you’re talking about, if you don’t have faith – you can’t get the job done. Evangelism is about winning hearts and minds, and people just know when you’re faking it, and once they know, they’ll never listen to you again.

Guy Kawasaki

I’ve wanted be a technical evangelist ever since I learned about Guy Kawasaki, who held the title at Apple in the mid 1980s. He may not have invented the title or the position – credit for that has to go to Mike Boich, Guy’s buddy at Apple – but he popularized the term and set the standard. The job engages both what we colloquially refer to as the “left brain” and the “right brain”; it requires you to tap into your rational and creative sides, often simultaneously. It’s the sort of work that I can really sink my teeth into. It is my dream job.

Nobody questions my suitability as an evangelist. People have asked about my suitability as an evangelist for Microsoft. How can a guy who’s been working largely in the open source world for the past seven or so years, mostly on a Mac, be an evangelist for The Empire?


Immigrant family on Ellis Island looking at the Statue of Liberty in the distance

I came to appreciate Microsoft’s tools after leaving my first job. In 1997, my friend Adam P.W. Smith and I left multimedia development at a shop called Mackerel, to go try my hand at building “real” applications at our own little consultancy. We wanted to graduate from building multimedia apps for marketing and entertainment purposes – software you might run once or twice and then discard — and start building applications that people would use in their everyday work to get things done.

Despite being Mac guys at heart, we chose the Windows platform since that’s what our customers were using, and opted to use Visual Basic to build our apps. Although it was considered “the Rodney Dangerfield of programming tools”, Visual Basic in the pre-.NET era was the best tool for producing great applications in a timely fashion that both we (and our customers, since they got the source code) could easily maintain. Our longest-lived application, a database of every mall in America written for National Research Bureau in Chicago, was first written in 1998 and its codebase lived on until a couple of years ago. In today’s world of ephemeral Web 2.0 apps, that’s an Old Testament lifetime.

Splash screens for "HPS Training System" and "Shopping Center Directory on CD-ROM"

Just as the best immigrants bring a little bit of their home culture and add it to the mix in their newly-adopted country, we decided to bring Macintosh user interface and workflow culture to the Windows world. We took care to write user-friendly error messages and also structured our applications so that you wouldn’t see them often. Our layout was consistent and everything was clearly labelled so you never felt lost in the application. And yes, we sweated over aesthetics because we felt that beautiful tools lead to better work.

Here’s the original application that we were given as a guide:

Original crappy SCD screen 

…and here’s our rewritten-and-redesigned-from-the-ground-up app that we built for National Research Bureau:

New and improved SCD main screen

(For more on what we did, visit the page where we showcase our work.)

A decade later, I find myself an immigrant in the world of Windows development, and once again, I want to bring a bit of the cultures from which I came and add it to the mix. This time, that culture is from Build-on-Mac-Deploy-on-Linux-istan, a cultural crossroads which blends a strong design aesthetic with the focus on the web, mobile applications, unit testing, distributed version control, sharing code and a scrappy startup work ethic and spirit. At the same time, I see the potential in my new Microsoft homeland, with its expansive reach into just about every level of computing, from embedded systems to giant enterprise datacentres, its excellent IDEs and frameworks and its large developer base. As an “immigrant” Microsoft evangelist, I see the chance for me to ply my trade in a new land that needs my skills, energy and outside perspective, and earn a fair reward for my efforts.


Shaman holding a Windows 7 logo

I’ve been trying to take how I see my role at Microsoft and distill it into a single idea, perhaps even a single word. The term “Change Agent”, which appeared all over the place in early issues of Fast Company captures a lot of what I’m trying to express, but it feels sort of clumsy and doesn’t have that summarize-a-big-concept-in-a-single-word oomph that “Evangelist” has.

Luckily for me, my friend Andrew Burke was reading an editorial in Penny Arcade which had the perfect word:

What Microsoft needs badly is a shaman. They need somebody who is situated physically within their culture, but outside it spiritually. This isn’t a person who hates Microsoft, but it’s a person who can actually see it. I can do this for you. Give me a hut in your parking lot. I will eat mushrooms, roll around in your cafeteria, and tell you the Goddamned truth.

That’s not bad. There are a number of ways in which “shaman” might be more applicable than “evangelist”.

Family photo where everyone except one kid is dressed in their Sunday best; one kid us dressed like a biker/metal dude.

For starters, I am situated physically within Microsoft’s culture, but in many ways I’m outside it spiritually. This is thanks to the fact that I’m a mobile worker and don’t have a cubicle within Microsoft’s offices and to my manager John Oxley’s efforts to keep me from getting too deeply entrenched within the culture. I was hired partly for my outsider’s perspective, and for me to be effective, I need to maintain some of my “outsideness”. This perspective makes me able to do or see things that a hardcore Microsoftie might not consider (such as Coffee and Code) or perceive (such as the rise of the iPhone, while Steve Ballmer said that “There’s no chance that the iPhone is going to get any significant market share”).

"Mediator" photo: guy in suit acting as a referee for two guys in suits arm-wrestling

Unlike religious evangelists, shamen are mediators. While an evangelist’s communication is typically one-way, from the supernatural to the people, the shaman not only speaks on behalf of the supernatural to the people to influence them, but also on behalf of people to the supernatural to influence it back. If I am only evangelizing to developers on behalf of Microsoft, I’m only doing half my job. I also need to evangelize to Microsoft on behalf of the developer community.

When I joined Microsoft, a number of my friends suggested that I’d be good at changing the company from the inside. I think that that task is better left to the people who either develop its technologies or strategy; as an Evangelist – er, Shaman – I am better positioned to change the company from the outside. Think about it: a good chunk of what makes a platform is its developer community; without it, it’s just sits there. Without their developer communities, Windows wouldn’t have become the dominant desktop system, Linux wouldn’t have become the dominant web OS and the iPhone would be another Nokia N-Gage. Developers shape the platform just as much as the platform vendor, and they do it best when they have a conduit to their platform vendor – a shaman.

Package for the Nintendo game "Captain Planet and the Planeteers"

For some religions, the position of shaman is also an ecological one, and as a developer evangelist so is mine. According to Wikipedia, some shamen “have a leading role in this ecological management, actively restricting hunting and fishing”. I am charged with making sure that Canada’s developer ecology is a healthy one; in fact, when I was hired, I was told that I was hired “for Canada first, and Microsoft second.”

A healthy, thriving developer ecosystem is good for the field, which in turn is good for Microsoft. As a developer who likes to participate in the community, I have an active interest in keeping the ecosystem healthy, and a Microsoft that contributes positively to that ecosystem is a good thing. The nurturing of ecosystems isn’t covered by evangelism, but it certainly falls under a shaman’s list of tasks.

Wide-eyed LOLcat hiding: "Bad trip kitteh wishes furniture would just stay in one place."

And finally, the idea of eating mushrooms and rolling around the Microsoft cafeteria is intriguing. I doubt that they’d tolerate me playing my accordion while high as a kite, wearing nothing but body paint and assless chaps, rolling all over the salad bar and smothering myself with cottage cheese. It is an amusing idea, though.


Where Should I Hold My “Coffee and Code” Days?

Guy in a cafe using a laptop

This article also appears in Global Nerdy.

From 1998 to 2000, I was self-employed. Lacking the funds to rent office space, I ended up working outside the boundaries of cubicle-land or even anything that looked like an office. I worked out of my kitchen, my business partner Adam’s living room and often by the bar at the old location of the Queen Street cafe known as Tequila Bookworm. Being a gregarious and social guy, I enjoyed working at “The ‘Worm”, mixing work with mingling with both the people who came to the cafe and the people who worked there (which led to a story I call Worst Date Ever, which was actually a lot of fun, even back then).

Today, I’m a Sith Lord – er, Developer Evangelist — at Microsoft. In addition to the cool red lightsaber and the ability to hurl lightning bolts, I also have the benefit of being a remote worker, which means I can choose where I work. I’ve got a nice home office setup and I can go hang out at the Evangelist Corner at the Mississauga office, but neither of these locations puts me anywhere where you can come up and talk to me.

That’s why I plan have a “Coffee and Code” day at least once a week. On these days, I plan to work from a wifi-equipped cafe, where you can walk right up to me and talk.

This brings me to my question: Where should I set up? A better way of putting this question might be “Where should I set up so that it’s convenient for you to drop by and have a word with me?” As long as it’s got wifi and it’s somewhere in Toronto, if it’s at a place that’s convenient for a lot of developers and techies, that’s where I want to be.

If you have any suggestions, please let me know in the comments!


My Inaugural Swearing-In Ceremony

This article was originally posted in Global Nerdy.

On Tuesday, the day that Barack Obama got sworn in as the 44th President of the United States, my 3-month probationary period at Microsoft also ended and I became a full-fledged Microsoft Developer Evangelist. I figured that if Obama could have a swearing-in ceremony to mark his official entrance into his new job, why couldn’t I?

As luck would have it, I was at the Vancouver Convention Centre to speak at Microsoft’s TechDays conference, where the Microsoft logo was projected onto the waterfall on the second floor. It made a pretty good backdrop for the ceremony, which was conducted by my fellow Developer Evangelist John Bristowe. I swore my oath on a “Techie Crunch” box, a cereal box containing the swag we gave to every attendee:

This magic moment would’ve been lost forever if it weren’t for videographer, blogger and man-about-tech Warren Frey, who was recording interviews for TechVibes and caught it for posterity. Thanks, Warren! I salute you with a filet mignon on a flaming sword!

It Happened to Me

2008: Annus Assrocketis (The Year of Assrockets)

Cork popping off a ribbon-ringed bottle of champagne

At the end of 1992, when the marriages of her children, Prince Charles, Prince Andrew and Princess Anne all dissolved and Windsor Castle caught fire, Queen Elizabeth II alluded to the title of John Dryden’s poem Annus Mirabilis (“Year of Miracles”) and referred to the year as an annus horribilis (“horrible year”).

As H.R.H. the Queen of England riffed on Dryden’s coinage, so shall I riff upon hers. If I had to summarize the year between 2008 in a quick soundbite, I would use the pseudo-Latin coinage Annus Assrocketis, as in “Year of Assrockets”.

Assrockets and Opportunities

A little bit over a year ago, I wrote an article titled Assrockets and Opportunities explaining why I was leaving my job as Tucows’ Technical Evangelist, a relatively safe, secure and cushy job – one that its CEO Elliot Noss said “fit me like a glove” — for a startup in the rather iffy social software space.

I had been feeling a little bit restless for a little while, but that restlessness alone wasn’t enough to make me take the leap. Strangely enough, it took a video of a guy sticking a bottle rocket up his butt and an observation made by Charles Follymacher in the blog The War on Folly. Assrockets and Opportunities summarized how the video and Follymacher’s blog entry inspired me to change jobs.

As a quick refresher, here’s the video. Be advised that it may not be safe to view at your workplace, as it shows a young man’s bare bottom and a bottle rocket stick being inserted into said bottom. It also has a lot of crude vernacular that young men are wont to use. That being said, I still think it’s one of the funniest internet home videos of all time and it still makes me laugh out loud, even after hundreds of viewings:

Still the funniest video of all time.

In response to this video, Follymacher, a person of colour (I myself prefer the term “force of darkness” – it has a little more oomph) wrote a hilarious and insightful observation titled why White people rule this age. The relevant excerpts appear below:

…I’m once again reminded why White people rule the globe. It’s not a new idea, just feeling compelled to state it once more, this time without feeling: they run the world because they have a much (much) higher percentage of folk who will do absolutely *anything.* any bloody, assinine [sic] thing at all. if you can name it, guaranteed it will be tried, if it hasn’t been already.

it is out of these absolutely stark, raving, barking mad experiments that new discoveries are made, which in turn lead to a fresh new batch of shit to fuck with. new answers urge new questions and all that, right?

us colored peoples of the world tend to leave well enough alone a lot more, not much for forcing Mother Nature’s hand. our ancient sciences are lost. that’s our bad. who knew? we didn’t ask. and now it may be too late to churn up that kind of insatiable hunger for knowledge.

a lot of White folk die off in these quests to discover and experience the unknowns, large or wtf. but some small percentage do manage to live to tell the tale and, wherever possible, wreak [sic] the profits.

I read the article in mid-October of last year and decided that it was high time I stuck a rocket up my ass, at least in the figurative sense. I put out a few feelers into the local tech job market.

Soon after that, I ran across an announcement of an open position at a startup looking for Ruby on Rails developers. The salary offered was a good deal better than my then-current one, and the opportunity to get back to writing code was very tempting. In five weeks, I went from replying to the offer to my first day on the job, the Monday after American Thanksgiving 2007.

Since that time, I have had three jobs.

The First Job (November 2007 – March 2008)

The startup I left Tucows to join – I don’t even like mentioning their name; you can look it up in this blog’s archives if you really must know – was building a Facebook-like web app for fraternities and sororities (“So you’re telling me that it’s like Facebook, but for students,” Cory Doctorow would say much later).

It might’ve stood a chance if it had these three missing ingredients:

  1. A business plan. The original plan was to make money by advertising. The sales guy came up with a much better plan – selling that app as a way for fraternity and sorority chapters to collect dues and charging them on a per-member basis — but it was too little, too late. It wouldn’t have hurt for the founder to have actually written down his business plan, even his lame-o first one.
  2. A product plan. The app was the result of “wouldn’t it be neat if this existed?” pipe-dreaming, and there wasn’t much thought or research put into it after that.
  3. A CEO who wasn’t just in love with the idea of running his own “Web 2.0” business and the associated trappings. He was hooked on the idea of creating office spaces with cool custom furniture like Joel Spolsky’s Bionic Office, “20% projects” like Google’s and “Hero Training”, in which we’d take a full day off work to do personal development. He also had some kind of fanatical belief in Ruby on Rails’ ability to solve any problem, from rapid development to world peace, curing cancer and fixing erectile dysfunction.

Truth be told, having missing ingredient number 3 might’ve given us missing ingredients number 1 and 2.

Montage of photos of the office for the first job
Click the montage to see the Flickr photoset.

Perhaps I’ll write about it at length someday, but for now a quick summary of what happened to this startup will have to suffice. They burned through money irresponsibly in many ways, including:

  • Renting office space in a pricey office building in a posh boutique district of town. We were located between the Mont Blanc and Ports International stores and across the street from the downtown Four Seasons.
  • Hiring an interior decorator to do a custom design of the office space, with custom furniture. I’d have kept the decent chairs, but we would’ve been just as productive with folding tables as we were with the custom desks.
  • Purchasing two large flat-screen TVs, neither of which were ever used for business purposes. They were pretty great for Wii and Xbox 360 games, though.
  • The ice sculpture and oyster shucker at the office-warming party. The party was black tie optional for some reason that still eludes me. At least they scaled down their ice sculpture purchase; they originally wanted the Chrysler Building, but settled for the less complex (and less expensive) company logo instead.

The ice sculpture at the office-warming party.
The ice sculpture at the office-warming party.

Alarmed at the company’s burn rate and lack of income, the source of the startup’s funding threatened to cut off the money. We were then informed by the CEO that unless we accelerated the schedule unreasonably, we’d all have to take a 20% pay cut. He went on vacation to Hawaii with his girlfriend a couple of days after that because he always went on vacation to Hawaii with his girlfriend at that time of year, crisis at his own company be damned.

While he was away, the entire senior developer team, of which I was part, started circulating their resumes and putting out the word that they were looking for new jobs. Within six weeks, the senior team had left the company. Within six months, the company had all but vanished. The website for the software no longer works, and the website for the company is now a single page showing the startup logo and nothing more.

My job at the startup, which had gone from dream to nightmare, lasted three months and a few days. The name of the startup still gets mentioned from time to time at local geek gatherings, sometimes as a cautionary tale, sometimes as a joke.

The Second Job (March 2008 – September 2008)

While searching around for jobs, I noticed that b5media was looking for a technical project manager. “b5”, as they’re often called, is a local startup success story, having grown from a small core of five bloggers and an office in Mark Evans’ garage to a network of over 300 blogs. I also knew that they’d landed funding thanks to meeting VC Rick Segal at DemoCamp, a semi-regular “show and tell” event for the Toronto tech community that I help host.

I showed up at b5media for an interview at 11:00 a.m. on one cold day in February, expecting a one-hour interview. It turned into a seven-hour series of multiple interviews with various people at the company, mostly testing me for how well I fit in with the office’s culture. I pretty much landed the job that day, and a couple of weeks later, I had my first day on the job, which involved flying down to Austin, Texas to attend the South by Southwest Interactive Festival for a week. I’d have to say that it was the best first week on the job I’ve ever had.

Regular readers of this blog know what happened in the end: changes in the market and at the company left me with nearly nothing to do, and they let me go…on the day of my wedding anniversary (they didn’t know that, but their timing still left something to be desired). I hold no ill will towards them; paying me to warm a chair does neither b5 nor me any good. It was the right thing to do, and they treated me quite well during the process.

Still, I felt like this:

Demotivational poster featuring dejected stormtrooper sitting on subway. Caption: "Unemployment: Sucks when your job is blow'd up."

The Job Search

The Unemployed "Stuff to Do" List

I decided to treat my getting laid off as an opportunity in disguise, a chance to explore all my options and do a little long-term career planning. At the same time, watching my old schoolmate Ali Velshi on CNN talking about the credit crunch and dealing with a worried wife meant that I should try to secure some income as quickly as I could.

I had one big thing working in my favour: nearly seven years’ worth of tech evangelism and seven years’ worth of blogging meant that I had a lot of what VC Howard Lindzon calls “social capital” in the bank. I did not have to go looking for job openings; they came looking for me. A number of people called, emailed, instant-messaged and tweeted me, asking if I’d be interested in working for their company and if I could make some time to meet them for an interview. The jobs ran the gamut from doing some development for an adult entertainment site to doing tech evangelism for some pretty high-profile companies. I did interviews with just about everyone who called me, which meant that I was actually busier as an unemployed man that I was during my last weeks at b5.

I even got a call from an editor at a very reputable book publisher in New York asking if I’d ever given any thought to writing a book. The answer, by the way, is “yes”, and as soon as an idea comes to me, I plan to fly down to Manhattan in a nice suit and do a pitch over cocktails, which if Mad Men is not lying to me, is how these things go.

Most of the companies who called were the type I’d always worked for: either startups or small operations where I’d have the ability to wear many hats, make a significant contribution and have a great degree of freedom. Medium to large companies were completely off my radar, but I’d have to say that it was mostly because I’d grown accustomed to thinking of myself as a small company man.

As a result, it seemed unreal when I got a number of calls from different people from the same organization, all asking variations on the same question:

“Have you ever considered joining The Empire?“

Imperial Considerations

LOLcat: "Pensive cat is not sure about that"

I’ll be honest: I had some qualms about joining Microsoft.

Fear of “selling out” and working for a big company wasn’t even a factor. It probably should matter at 21, but not at 41. To borrow a saying often misattributed to Churchill: if you’re not at least a little liberal at 21, you have no heart; if you’re not at least a little conservative at 41, you have no brain.

There’s also the standing order from The Missus: “No more working for fucking under-30 CEOs!”

Finally, consider the great truth expressed in the comic below:

Congratulations! You kept it real and never sold out! Now you're "the old guy!"

My qualms didn’t arise out of loyalty to Apple; they make some really nice machines and an excellent OS, but I’m not really one of those “It’s Apple or nothing” types. They also didn’t come from an “open source forever, Microsoft never!” feeling either. Open source has resulting in some great things happening, but once again, I’m not a “F/OSS or nothing” kind of guy, either.

My qualms came from the feeling that Microsoft had little to offer to me as a developer. Once upon a time, back when my friend Adam Smith and I had a little software development constancy, Microsoft was my friend. From the mid-1990s to the release of .NET 1.0, it felt as if they were constantly reaching out to developers. Then somewhere along the way, at around the same time as the rise of web applications, Apache, PHP and later things like Rails and Django, something happened. Microsoft had apparently switched their focus away from developers and towards the suits – the decision-makers who approved the tech purchases, rather than the people who actually had to live with the decisions. I’m sure that many developers felt the same way I did: Microsoft slowly faded from my radar because it seemed as if I’d faded from theirs.

I think that my friend Danny O’Brien expressed this best when he wrote:

One of my big bones with MS stuff is that it always makes me feel like I’m eating out of the trash bins outside a cubicle farm. All of their software is designed to help busy executives plan their lives. Everyone I know uses it to try and write birthday cards and chat with their friends. When people use Microsoft Office they use it anywhere but in an office. Microsoft knows this – but it also knows that the money comes from their corporate clients, so there’s a limit to how much it can bend its software toward a wider customer base. Ultimately when you use MS software, you’re not the end user MS perceives at all: we’re just living off the scraps Microsoft leaves out after feeding its big customers.

One thing that convinced me to join Microsoft was a small-seeming but important sense of a “sea change” at Microsoft.

Perhaps it was their hiring of some people I’d never expect: David Crow (I’ll admit that I was ready to bet some good money on his leaving within six months, saying “It’ll either end in tears…or gunfire”), Bryce Johnson, John Lam and Danah Boyd.

It might have been their willingness to even consider talking to me after my posting this graphic on my blog:

"I'm a Mac." "I'm Unix." "I'm Vista."

It might have been some very lengthy conversations I had with friends who worked at Microsoft.

It might have been this thing:

XBox 360

I won an XBox 360 at the 2006 Boston Ajax Experience conference, and I was surprised at how much I loved it. It doesn’t feel like a “Microsoft product” – it feels like something built by people who love games for people who love games. The “Less Hulk, More Bruce Lee” story behind the design of the XBox 360 that Jean-Luc David told me probably helped as well.

Mark Relph and John Oxley

What probably convinced me most was the opportunity to work for a couple of great people who believed in me, Mark Relph and John Oxley. They offered the combination of a lot of support and a great deal of latitude, the ability to work largely from the home office and most importantly, the freedom to inject my own personal style into the work I’d do. I think Mark’s line, “We enter as friends, we leave as friends”, struck a chord with me.

At the end of my sixth(!) interview, John said “We’d like to take you on. Are you interested?”

I replied “To quote Homer Simpson, I have only two questions: ‘How much?’ and ‘Give it to me!’”

In the end, I was unemployed for a grand total of three weeks. Considered the economic collapse taking place all ‘round, that’s not bad at all.

Fry-Kirk Syndrome (or: The Third Job; October 2008 – Present)

Philip J. Fry from "Futurama" and Captain James T. Kirk

At the dawn of 2009, just over a year after leaving my tech evangelist job, I have escaped from one imploding company, been laid off from a downsizing one and finally ended up at a job that fits me like a glove. After this journey, I have become…a tech evangelist.

I feel like “Fry” from Space Pilot 3000, the premiere episode of Futurama. Fry, a p[izza delivery boy in 1999, is frozen on New Year’s Eve 1999 and revived a thousand ears later. In the year 3000, a computer determines that he is best-suited to being a delivery boy, and he spends much of the episode trying to escape this fate. In the end, he cheers as he finds work with a distant relative…as a delivery boy.

Captain Kirk had a similar experience: he always returned to his first, best destiny – being captain of the Enterprise. I feel that I’ve managed to do the same, and with the added bonus of not having a court martial, blowing up the ship, losing my son and getting demoted from Admiral.

Like the young man in the “Bottle Rocket” video near the start of this essay, I took some risks and got a little singed in the process. But as Charles Follymacher also pointed out, sometimes you “manage to live to tell the tale and, wherever possible, wreak [sic] the profits,” and that’s what happened to me in the end.

As any decent poker player will tell you, winning isn’t in the cards you’re dealt, but how you play them. In spite of all the craziness this year, I did quite well.

I’m looking forward to 2009.

[This article also appears in Global Nerdy.]