As promised, I’m going to begin featuring some of my favorite Mad Men scenes in which Don Draper practices exquisite creative communication. Today’s episode: Lucky Strike.

One of the most thrilling parts of my job is pitching our creative ideas to clients, whether it’s when we’re trying to win new business or during the actual development of a project. In either case, several creative communication challenges arise:

1. Getting the client to understand our ideas
2. Inspiring the client to give us productive feedback on our ideas
3. Convincing the client that our ideas are good

The first two cases are simply a matter of good two-way communication: every one of our presentations is a conversation between the creative team and the client, and our ideas can and should be shaped by that conversation.

But the third challenge kind of flies in the face of the first two. It’s a sales process, where we need to stand tall and back our ideas with confidence, selling the ideas, convincing the client that our idea is correct — sometimes even if the client’s feedback pokes a few holes in our concept. Of course the best way to keep a client happy is to simply have great ideas and great follow-through on those ideas. But without confidence in your ideas, you’re risking preventing great ideas from succeeding.

All creative people question their ideas — If I thought about it more, would I come up with something better? Has this idea been thought of before? Am I totally off base? But if you can’t stand up for your own ideas, then those ideas wont be given a chance to develop and get better. Ideas are like living things, weak when born but growing stronger as they overcome challenges, learning from failures and mistakes. Without confidence to drive it along and protect it, a perfectly good idea might be nipped in the bud before it becomes truly great.

Lucky Strike

This clip exemplifies all of these challenges. A little background: Don Draper, in typical Mad Men fashion, has been, shall we say, distracted from work and has arrived at this pitch meeting completely unprepared (I don’t advocate this, but hey, that’s Don Draper). The client is the maker of Lucky Strike cigarettes.

The year is 1960, and America is just starting to learn that cigarettes are actually dangerous to your health. Many people forget that cigarettes used to be marketed as great for your health, helping you stay slim, fighting infection, and all other manner of ludicrous medical claims.

First, let me say that I love watching the dramatics of Sterling Cooper’s pitch meetings, which happen in almost every other episode of Mad Men. As it is with Behavior’s pitches, the Mad Men agency team has a functional dynamic — one person focuses on the company’s credentials, handing off the creative proposal to another. Unlike at Behavior, however, Sterling Cooper’s creative team is embroiled in a cutthroat competition as Don Draper and the young Pete Campbell. I suppose that’s life at a large agency.

In this pitch, the client is given a chance to explain their situation to the agency first. Don Draper listens intently, but when he steps up to bat he immediately strikes out. Okay, so far Draper’s lack of professionalism here is unforgivable. Pete Campbell has a backup idea. But his idea is even worse, and doesn’t take into account the client’s profound belief that cigarettes are wholesome.

Draper, however, has been mulling over his client’s concerns. His initial thinking, when he finally unleashes it, is inspired completely from what his clients told him about their product — that they are really no different from their competitors. But that’s just the start. He immediately engages the client in a conversation about his concept, looking for something meaningful to latch on to, to complete his idea.

After a rapid brainstorming exercise with the client, the idea crystallizes: It’s Toasted!

Then, critically, Draper stands behind this idea 100%. He’s even willing to argue with the client over the idea. “They’re all toasted,” says the client. Draper’s argument makes no logical sense. But he believes in it, and will argue passionately for it, because the idea is a quintessential Don Draper idea, one based on emotion instead of logic. He has transferred the conversation from one about medical health to one about happiness and assurance.

Hopefully I’ll be able to keep these copyrighted — but used here under journalistic fair-use — videos posted here. And please stay tuned for more!

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The NeXT Cube and the Apple Mac Cube. Are they iterations?

Discussing his upcoming biography of Steve Jobs, author Leander Kahney describes Apple’s prototyping process:

It’s a process where they discover the product through constantly creating new iterations. A lot of companies will do six or seven prototypes of a product because each one takes time and money. Apple will do a hundred — that’s how many they did of the MacBook. Steve Jobs doesn’t wake up one morning and there’s a vision of an iPhone floating in front of his face. He and his team discovered it through this exhaustive process of building prototype after prototype.

Clearly Jobs wants to see his team exploring hundreds of prototypes of his products before a final version is sent to manufacturing. But when asked in a video interview about his experience hiring the legendary graphic designer Paul Rand to design of the NeXT logo, Jobs said he admired the fact that Rand (perhaps arrogantly) proclaimed that Jobs would only get one logo for his engagement fee. Rand would not show Jobs a menu of variations to choose from, nor would he show a selection of rough drafts and allow Jobs to provide feedback so that Rand could go back to the drawing board to produce a final candidate. There would be no process at all, no open exploration — Rand would simply give Jobs the best logo he could provide, and then Jobs could take it or leave it.

Why would Jobs admire Rand’s process so much when he runs Apple’s design team in exactly the opposite fashion? Is it simply a matter of Jobs being a sucker for Rand’s monumental ego (and, of course, his stunning track record) while still being a absolute monarch with his own internal team?

This touches on a bigger issue in the design profession: When should a design process spend time on a broad exploration of many options, and when should a designer or design team focus on perfecting a single promising idea?

My inclination is almost always to explore as many options as possible, only settling on a final direction when practical constraints force me to get busy finishing the product.

Of course, this is just one school of design. Clearly many other designers prefer to finish their explorative thinking early and to then invest the bulk of their effort on perfecting the product. Still other designers are simply incapable of coming up with more than a small number of ideas — or they are temperamentally prone to become extremely emotionally attached to their earliest ideas.

In which contexts is a quality-based process actually preferable to a quantity-based process?

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I am going to be speaking today, June 17th, at the OMMA Publish conference here in New York City, on a panel entitled “Optimizing for Performance: Adding Value to Your Site”. OMMA is focused on online media marketing and advertising, publishing several trade magazines and sponsoring several conferences each year in these areas.

My panel will discuss the seemingly straightforward topic of making media sites more engaging and (critically) more profitable. The session will cover the spectrum from tactical solutions — new features that increase stickiness and page views — to strategic solutions that fundamentally change what your media web site can be for the audience and users.

And then, of course, there is the middle ground between tactics and strategy, the recognition that all of the little things we do to improve the user experience and to delight the user actually add up to a strong overall brand experience.

This is my first conference in which I am not speaking to an audience composed almost exclusively of design professionals. While there will certainly be peers and colleauges in this conference, many of the attendees will be members of that elite, special class of individual I call potential clients. I’m usually a pretty good pitch man, so I think this will be fun.

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Two months ago, I tweeted the following cry for help:

Over the last several months I have made some tough choices about what to devote my time to. And “blogging”, unfortunately, didn’t make the cut.

In short, I have been extremely busy doing things other than blogging. In the next week or two I will try to write a few more detailed update posts about my recent shenanigans, just to get it all on the record. But for now, here’s a rundown of some of the things that have been keeping me away from graphpaper.com:

• I’ve been intensely working on some big time client projects at Behavior. We’ve launched a few major awesome web sites.
• I presented a workshop at the IA Summit in Miami, and had a technology misadventure.
• I went to SXSW, but thankfully I wasn’t a speaker this year.
• I attended and made a short presentation about iPhone design at an iPhone BarCamp, and showed off some iPhone design experiments I’ve been working on.
• I’ve been serving on the advisory board for the O’Reilly Web 2.0 Expo NYC.
• I did a couple of interesting magazine interviews.
• My triathlon training has gotten more intense. I raced in a duathlon and placed 23rd out of 120+ competitors.
• I had some great times with friends and family. Seriously, this was the best part of getting off the blogging wagon.

And here are a few things coming up in my future:

• I’ll be a presenter at An Event Apart Boston in June.
• I’m taking a personal vacation in LA right after AEA.
• I’m competing in the NY Triathlon in July.
• I’m preparing to start teaching again in a new MFA program in interaction design.

Finally, a word on the weather.

It’s well known that everyone (at least those of us who live in climates with seasons that change) undergoes a certain degree of seasonal affective disorder, where the dark cold months of winter dampen our mood and our energy and where the sun and warmth of spring and summer lift them up again. I’ve never thought of myself as particularly susceptible to this phenomenon, but this year I learned that I am, and profoundly so.

Which is to say that now that spring is here I feel great and have a new sense of purpose, optimism, and ambition for the months ahead.

I am back!

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I have a tendency to be extremely skeptical about user research in the design process. This is mostly because so much of it is, IMHO, (a) fundamentally bad (e.g., employing sloppy research methods or hamfisted statistical analyses), (b) flatly dishonest (e.g., dressing unscientific research in pseudo-scientific drag in order to justify a desired result), and (c) runs against what I think to be effective design methodologies.

I’m beginning to think my distrust runs even deeper. So deep that I fear I may be gaining a reputation as a “research curmudgeon” who’ll always have a knee-jerk dismissal of any new or clever techniques that pass under my nose. This may be true — I may be overly skeptical sometimes.

But now I think I can explain it with a little more nuance than before, and offer a new and largely positive perspective on research as part of a design process.

In the past, my scorn for user research has been aimed at everything from baroque user persona proceses to no-duh eyetracking studies. The latest technique I reflexively scoffed at is “modemapping” (pointed out to me by David Armano), a technique developed by Stuart Karten Design. Thinking more about the potential uses of modemapping made me realize that my scoffing was not directed so much at the technique itself, but that, instead, I have a deeper problem with the formalization of design research in general.

First, what is modemapping? Well, it’s not so much a research gathering technique as it is a method of interpreting data. To produce a modemap, researchers first interview and observe users (no differently than they would for any sort of primary ethnographic research). Then they use the data to diagram each user’s behavior on a timeline-like chart. The resulting “modemaps” visually distinguish between different types or modes of activity a person may find themselves in during a given timeframe, such as during a typical weekday.

To someone like me, a lover of information graphics (and in particular of timelines), modemapping did have an immediate visceral appeal.

When I thought a little more about modemapping, however, I asked myself: Could the observations gleaned from these modemaps really be any different from — or better than — the observations that a good researcher could have gleaned simply by conducting the interviews, reading the transcripts, and watching the videos? Is this just a way to spend an extra week or two of research budget to develop fun graphics? Is this just infoporn that looks hot but doesn’t reveal new information or insights about the underlying data?

But then I realized that this kind of seemingly-pointless abstraction is exactly what I do when I make a jump from facts to ideas, from thinking to designing. For me it’s not the diagram or the artifact that matters. It’s the process of making the diagram that produces innovation. The most powerful design insights do not simply emerge from the diagram for any third-party viewer to read as if they were reading a billboard. More likely the design insights enter the mind of the diagram-maker while they are assembling it. The final modemap artifact simply serves as a tool to explain the designer’s inspirational process to other people (non-designers, especially, but also to other designers) in the hopes that the customers of the diagram (whether they be clients or collaborators) may understand the merits of the design. The diagram may even, in fact, be let incomplete or even discarded upon completion if the design insights may be better expressed through another means.

My Design Process

When I am designing, I almost always do tons of research first. But at some point I will start doodling and sketching different ways of making the data mean something. I try to visualize and organize the facts into systems. I’ll go through dozens of quick and wildly different sketches of how the data might fit together, almost always with no idea of how the sketching process will end up.

Quite frankly, much of this time might even be spent staring into space and just thinking, visualizing the data in my head. Sometimes the resulting sketches will resemble or even closely conform to known data interpretation techniques such as mental models, flowcharts, affinity diagrams, Venn diagrams, quadrants, and many others. I’ve probably used half the techniques in the visualization periodic table without even knowing it.

The “not knowing it” part is where my user research curmudgeon-ness comes in. I have a passion for letting my mind wander freely and letting it discover revelatory and meaningful visualizations. Rather than letting the visualization lead my idea process, though, I let the idea process generate the visualization. Because I prefer this way of thinking and designing, I have an immediate disdain for any methodology that purports that a particular data interpretation or visualization technique is the right one for a job. How can a great designer know what tools they will use before the design process begins? They simply can’t.

It’s a fundamental quality of design thinking, I suppose, to let the ideas determine the process. What veers us away from design thinking and towards (for lack of a better term) business thinking is the formalization of a research and research interpretation process. Instead of asking researchers to bask in the data using whatever methodology suits their temperament and idiosyncratic thought process, commercial design culture often asks the design researcher to fit their research into a proscribed process, in this case the “modemapping data interpretation machine”. The techniques themselves don’t demand this — the demand for pre-planned processes comes from business constraints where customers need to know what they are paying for.

This is a real conundrum for the research-minded design thinker who needs to keep to a budget: How do you sell a research-based methodology if you cannot say for sure what research-interpretation method you will use? How do you productize or justify the value of “staring into space for a few hours thinking about the problem”, or “sketching in a moleskine for a few days”?

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On the IxDA list this week, Lisa deBettencourt asks:

What are your fundamental tenets of design; those little bulleted phrases on the Design Vision slide of your Powerpoint, the signatures on your email footer, the philosophies you work by as you design?

A simple but interesting question. You can see all the answers here, but here’s my quick, stream- of- consciousness answer, below. Almost everything I’ve written below is something I’ve actually thought of or said before.

(I just want to be clear, though, that this is how I work, personally and professionally. I make no claim that working the way I do will lead to success for other designers, other design firms, or for the practice of design as a whole in a capitalist system.)

• Do work you can be proud of.
• Work for clients and bosses you like and can be proud of. Show sleazebags the door.
• Don’t lie.
• Understand that your audience is not you (and learn who they are), but always treat your audience how you would want to be treated.
• Don’t worry about the longevity of your ideas — much of what is truly great is perfect for the moment but ultimately ephemeral, while much of what lasts is crummy and is only remembered for nostalgic reasons.
• Generate ideas constantly. Write down every idea.
• Design can happen first, even before a need or problem is identified.
• But design isn’t just “a good idea”. It’s a good follow through, too.
• Think hard and work hard: 90% of your time will be spent dreaming up your ideas. The other 90% will be spent implementing them.
• Make ‘em think: Don’t be afraid to be a snob. Some people just won’t get your idea without thinking about it. Some people just don’t want to think. But those who do will appreciate being challenged.
• Make ‘em laugh: Don’t be afraid to be a goof. Some people have no sense of humor, but you’ll be surprised who does.
• Style is great. Fads and fashions are fun. There are plenty of design contexts where stylishness is critical — and there is no design context where a sense of style is completely inappropriate.
• Share your design ideas. No idea is so good that keeping it secret helps you. If you don’t build it, that’s your problem.
• Design is a funny kind of collaboration: Two designers are better than one, but only one designer can drive.
• Design is fun.

What about you?

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It’s hard to understate the pride I felt on behalf of my colleagues at Behavior when I read these words in Friday’s New York Times:

The Museum of Modern Art’s elegantly plain exhibition of Georges Seurat’s drawings begins with an unexpectedly extraordinary moment of computerized art viewing. Seurat’s four surviving notebooks have been converted to electronic versions that — with a touch of a finger — visitors can flip through, page by digital page, from cover to dog-eared cover. (The real notebooks can also be seen under glass nearby.)

Facsimiles they may be, but they instantly communicate the show’s intent, which is to clarify the way the silent, classical remove of Seurat’s impeccable, stylized paintings was distilled from an active, socially aware engagement with the world that registered most fully in his drawings.

If you haven’t guessed already, the touch-screen interfaces in question were designed and built by my studio mates at Behavior, both as kiosk installations in the MoMA exhibition gallery and viewable on the web as a gorgeous online exhibition.

Roberta Smith of the Times is one of the the most important art critics around. So when the opening sentence of Smith’s review of Georges Seurat: The Drawings focuses so enthusiastically on the interactive kiosk that my colleagues put together these past few months, it’s more than just praise for Georges Seurat and for the great curation and leadership by the team at MoMA. It’s also praise for Behavior.

Touch Screens in the Age of the iPhone

Most of the Behavior folks attended the exhibition’s lavish opening festivities last week, and we all got a chance to watch dozens of very fancy people interacting with the twin touch-screen kiosks. It was such a joy to watch the gallery-goers flip through the pages with looks of, I swear, genuine delight on their faces. No lie: I definitely heard “ooohs” and “aaahs”.

As with any usability test situation, of course, there were also the occasional moments where a user would try to do something we didn’t think of. Of particular interest was the fairly common attempt by users to treat the traditional touch screens as if they were iPhone-style multi-touch screens. People expected to be able to smoothly zoom in by spreading two fingers apart as they can on the iPhone. As with so much of what Apple does, the bar has apparently been raised in unexpected new places in the interactive landscape.

What About the Art?

Oh, and the show is absolutely luminous. I hope you check out the web site, of course, but if you enjoy art at all you must see the show in person. The sketchbooks are just a tiny piece of the exhibit. The rest of the show, and the online exhibition, includes drawings and paintings, historical conservation information, and of course the sketchbooks.

The exhibition is getting rave reviews from many other sources as well, and deservedly so. We’ve all seen Seurat’s famous pointillist paintings, especially the revolutionary A Sunday Afternoon on the Island of La Grande Jatte. But Seurat’s drawings reveal the intense thinking and talent that went into his painterly work.

The drawings excel in two areas simultaneously: Form and light. In a vivid metaphorical image conjured up by my wife Peggy (seen above), some drawings suggest that 19th century Paris would be transparent or even invisible if not for the industrial-era soot filling the air and collecting on any and all solid objects and forms. The charcoal on the page reflects the density of the matter in the space.

And yet other drawings emphasize light itself, with the space articulated only by where the light exists and where it does not — where traditional drawing marks like contour lines are banished. The relationship between this thinking and the daguerrotype photography of the time is hard to dispute.

The best works attack form and light at the same time, and it’s easy to see how Seurat’s eschewing of contour and lines — and embrace of volume and light — leads directly to La Grande Jatte, even without the extraordinary discoveries in color he is most famous for.

La Grande Jatte was painted when Seurat was just 26. He would die five years later, at 31. It’s staggering to imagine what he would have gone on to accomplish had he lived into the age of Matisse (born the same year as Seurat), Kandinsky, and Picasso.

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Yours truly, art student at Cooper Union in 1993.

I’ve been in some interesting discussions lately about “design thinking“, in particular with respect to the question of education: How are business and design educations relevant to the management of a design-centric business?

One of my core objections to the “d-school” concept is that most of the curricula emphatically don’t teach design skills. Instead, they teach “design thinking”, which is said to be a way of approaching problem solving that is inherently different from, I suppose, business thinking.

Well, like a fish who doesn’t know that he is wet, I have no idea what it is like to not be a design thinker. And I suppose that, conversely, a lot of people who talk about design thinking have no idea what designers are actually taught. Are we really taught different skills than our MBA counterparts? Is there really something unique about what designers are taught, about how we think?

To answer those questions, I thought it would be useful to simply talk about what I learned in art school. I’m not talking about the specific skills and crafts — I learned how to cast acrylic resin, how to weld steel, how to do 3D modeling, how to paint in fresco, and how to etch a circuit board — although I do strongly believe that hands-on design experience is crucial to being a good design leader.

Instead, I am talking about the broader and more resonant skills I’ve learned that have helped me both as a designer and as a business person.

This is meant to be a dialogue. If you went to art school, did you learn these kind of things? More importantly, if you didn’t go to art school, did you not learn these things?

Without further ado: In art school, I learned:

• How to champion and defend my ideas.
• How to distinguish between personal and professional critique.
• How to respectfully and constructively critique my peers. How to attack the ideas of my colleagues and still have drinks with them that same night (and maybe even sleep with them — hey, it is art school)
• How to test drive a hundred different ideas through sketching, cobbling, and envisioning them, before finally settling on which one to go ahead and build.
• How to tell when I am done a project that could just as easily be improved endlessly.
• How to tell when an idea that is precious to me is actually holding me back. And then to feel good about throwing it away.
• How to have the confidence to present my ideas in public without fearing that they will be stolen. And how to take it in stride when they inevitably are.
• How to distinguish between taste, technical skill, and empirical efficiency.
• How to detect bullshit, and to avoid generating it myself (note that not all art school grads learn this).
• How to go the extra mile to make something high-quality.
• How to recognize talent in my peers.
• How to collaborate with my colleagues effectively to reach a common goal.
• How to be deeply competitive without being a dick.
• How to make something new just for the sake of being new.
• How to build off of, and give credit to, the ideas of my predecessors both contemporary and in history.
• How to save ideas that I’m not ready for and keep them for future use (usually in sketchbooks).
• How to start all over again from the beginning.
• How to teach all of the above.

I’m sure I could go on. Let’s just say that I definitely apply a lot of these lessons in my job every day, both in my own designs and in the way I work with my teams. Does this make me a design thinker?

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In the future of Idiocracy, Carl’s Jr.’s slogan becomes “Fuck You, I’m Eating”… which isn’t really a stretch from the attitude expressed in their current ad campaign.

David Armano’s Logic+Emotion blog today discusses a tacky new ad from Hardees & Carl’s Junior, in which a pair of smarmy white high school kids rap about their stripper/teacher’s “flat buns”, intended to introduce the world to their new “Flat Bun Burger” product. The ad really is just too stupid to describe, and I won’t even bother put the video of the ad here, since David has already (and reluctantly, by his own admission) put the ad up on his own site for you to see.

The commercial seems like a scene right out of the excellent and wildly-underrated movie Idiocracy (directed by Mike Judge, of Office Space and Beavis and Butthead fame). In the not-so-distant future in which Idiocracy is set, Carl’s Jr. is one of the dozen or so corporations who essentially control a world populated entirely by people with below-50 IQs and whose culture has devolved into shameless gluttony, juvenile sexuality, and crass violence. A professional wrestler is President, law degrees are sold at Costco, slot machines are in hospitals, and lounge chairs have food-dispensing hoses and toilets built into them.

This ad only helps to cement the movie’s profound prescience about the reality of our rapidly-dumbing culture and the overall downward trajectory we often seem to be heading towards, often hand-in-hand with corporate consumer marketing. In fact, every day I see a dozen commercials or products that seem right out of the future world of Idiocracy — but I see them right here in 2007 America. The movie is a satire, of course, but as with all the best satire it frequently and repeatedly hits shockingly close to home. (Happily, you can go ahead and view lots of hilarious scenes from Idiocracy on YouTube right now.)

On Human Dignity

I work on interactive marketing for some major consumer brands, but I am perpetually grateful that I never have to work on ads like this. Behavior’s clients are almost exclusively blue-chip brands with deep respect for their customers, users, and audiences. But many designers are sometimes presented with the option of either doing something classy or doing something crass and degrading. We have a choice between treating the customer with respect and treating them with contempt. The makers of this ad are either morons (which I doubt) or people who think of their customers as moronic assholes ripe for exploitation.

In fact, in the comments on David’s blog there is much speculation about the creative meetings in which this ad was hatched. I can only say that if I were working at a company producing ads like this, I would fight hard to do something classier, or I would quit and go work for someone a little less cynical about respecting human dignity. I don’t want to be one of the architects of the Idiocracy future.

As designers of experiences and shapers of brands, we do have a choice in this matter, even when working for clients who may have an inclination to “go negative” and tap into this poisoned well. Even if you suspect that an ad like this would actually work, that it would actually succeed in bringing millions of people into Hardees/Carls Jr. to buy these flat bun burgers, you have a responsibility to the inherent dignity of the human race to NOT produce ads like this.

Note: It’s not the sexuality of the ad I object to. I still think Van Halen’s “Hot for Teacher” (the obvious inspiration for this spot) is cool. The music’s kinda catchy, too. There’s just something about the whole thing, maybe it’s the over-the-top glorification of juvenileness and stupidity, that makes me sad for everyone involved with this ad and the millions of other cultural products like it that crowd our media landscape more and more.

Do you work on marketing that relies on these themes of disrespect, selfishness, immaturity, and stupidity? If so, how do you justify it? Do you have a choice in the matter, or do you feel that you have a higher obligation to give your clients or your customers what they seem to crave?

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As I was subtly hinting at in my last couple of posts, I have changed my Windowy ways. I have switched (back) to Mac. Finally.

This is the first in an ad hoc series of articles documenting my experiences with this transition, looking at it from many perspectives: personal and cultural observations, usability and user experience design inspirations, and technology and business considerations. And, not least of all, I hope that it will also serve as my formal introduction to the Mac community that I have for many years only been able to observe from the outside.

How I Became a Windows Addict

After college, when I landed my first real multimedia-industry job in the early ’90s, I was required to use Windows (version 3.11) as my day-to-day work machine. I had never used Windows before — in fact, I’d never even seen Windows before. I instantly found it awkward to use, and I immediately recognized it to be a lower-quality imitation of the Mac OS. Still, it wasn’t long before I owned a Windows PC at home.

Little did I know that this would be the beginning of a thirteen-year relationship with Microsoft Windows.

Earlier in my life, between the ages of twelve and twenty-three, my computer platforms were very diverse, including the Apple II, the TRS-80, the TI-99/4a, and the only computer I actually owned myself before the age of twenty-five, the Commodore 64. My father had a Mac SE, and I experimented with Hypercard on it in High School. Later, as I made my way through art school at Cooper Union, the professional platforms of the Mac and the Commodore Amiga became my tools of choice.

At college, I focused on conceptual installation and sculpture. I didn’t take any design courses whatsoever. I was cutting steel and casting plastic and reading about Marcel Duchamp, not learning how to use Photoshop or manage Suitcases. As a result, my exposure to the Macintosh was unusually light compared to that of most people who would become design professionals. What’s worse, back in the early 90’s Cooper Union’s design department owned all of the art school’s Macs, and they were very strict about who could use them. For several years you were literally not permitted to use the computers in the Mac Lab until you had completed several prerequisite courses in setting movable type in a medieval letterpress! Very old school policy, one that pretty much put the Mac out of reach for me.

And then Windows entered my life.

In all the intervening time, over a dozen different computers, four jobs, and starting my own company, I never went back to Mac. I just kept renewing my vows with Windows. Has it really been thirteen years? It’s hard for me to even believe it.

Why I Waited So Long to Switch

Computer ownership involves a lot of inertia, a comfort with the status quo that’s hard to overcome. You become invested both in your own expertise and in the tools you own. In my case, I became a bona fide Windows “power user”, and a pretty decent Windows system administrator to boot, and I accumulated an extensive collection of PC components and peripherals, piled up in drawers and toolboxes all around my home office.

My reasons for sticking with Windows for thirteen years are pretty simple:

Games: My career began as a computer game designer. Naturally I was also a player. And all of the best and most innovative games in the mid-90’s were PC-based (this was in the console “dark ages”, the lull between the NES and Playstation eras). Desktop PCs were miles ahead of everything else, and the Macintosh was barely on the radar at all. One can only play so much Sim City, after all. From the classic graphic adventure games from LucasArts, to the great isometric sims and strategy games from Warcraft to Civilization, to the thrilling genesis of the first person genre with Doom, Quake, Half-Life, and Unreal, I was up to my knees in pixilated blood thanks to the smokin’ PC platform. The Macintosh offered me nothing.

Now, of course, the Mac has plenty of games available for it. And honestly I have less interest in games than I did five or ten years ago. And the best gaming, of course, is on the Nintendo Wii anyway.

Tinkering: One of the things I liked most about PCs was how easy and cheap it was to open them up and experiment with the hardware guts, and how much software there was for further mucking around. It wasas if I owned a fancy sports car that I could trick out in the garage every weekend. Over the years, I’ve built dozens of PC computers from scratch, scavenging parts from older computers, discount stores, and even from the trash. I’ve also accumulated a lot of software: apps, utilities, hacks, tweaks. But in the last couple of years, I have retired from my hobby of tinkering with computers. The first step was realizing that the amount of money I save by building a PC from scratch was not worth the hundreds of hours I’d invariably spend dealing with hardware incompatibilities, OS glitches, and assorted Windows and PC bullshit.

At some point I decided that I should be using my computer for things besides playing with my computer. Getting a Mac is definitely part of this philosophy.

Cost: In 1997, before the iMac came out, I could build three smokin’ Windows workstations for the price of a single low-end Mac. Even after the low-priced iMac came out, I really never saw the Mac as an affordable computer given my budget and salary at the time.

I’ll be frank here: The Macintosh has always been a luxury product, targeted at the higher ends of the American economic class scale. And even now that Apple’s pricing gets comparatively lower and lower, there are still millions of people who cannot justify the cost of a Mac when a powerful new Windows machine can still be had for half the price. It’s a Wal-Mart mentality, making significant sacrifices on style and even quality in favor of price, but it’s an approach that I can hardly begrudge millions of Americans for taking when the other option is economically impossible.

As much disdain as I have for the Windows PC platform, I will not stoop to berating people just because they cannot afford a fancy Macintosh computer. I’ve been there, and I know how it feels.

Which brings me to probably another reason lots of Windows users resent the Mac: It’s a class thing. For a long time, I didn’t want to identify with style-conscious and wealthy computer buyers who were willing to pay twice as much for something just because it carried a certain cachet. Conversely, there’s a certain admirable asceticism to using a PC, like wearing a hairshirt. I’ve gotten over it.

Visio, Project, and Outlook: At various stages of my career, Microsoft Project and Microsoft Visio have been the centers of my professional computing life. As a project manager, MS Project is the essential project planning tool in the business world, and as an information architect, Visio has always been the industry standard. And Outlook has always been my dashboard for my business PIM needs. I am an expert power user of all three of these programs, and all three are only available on Windows.

The emergence of windows-compatible Intel Macs have made all of this obsolete, since now Mac owners can run Windows on the same machine via Boot Camp, Parallels, or VMWare Fusion. In a pinch, I can always run these apps in a Windows partition on an Apple machine.

But more importantly, I have come to have faith in the emergence of alternative, non-MS tools for every single application MS currently has a stranglehold on. Tools that are not only just as functional as the MS products they seek to replace, but that are already achieving an astonishing amount of adoption momentum. People are using non-MS apps more and more every day, including, surprisingly, many people within our enterprise-level clients. OmniGraffle is fast becoming the preferred alternative to Visio among my fellow information architects, for example, and tools such as Merlin and are viable MS Project replacements.

But more generally, tools that go beyond the desktop and aren’t mere feature-by-feature replacements. Google Spreadsheets, for example, is superior to Excel for much of my spreadsheeting needs: I can share it over the internet, it saves versions automatically, and it’s far easier to use than Excel. 37Signals‘ Basecamp and Backpack do a lot of things that no project management or PIM software does. Google, Yahoo!, AIM, Twitter, and Wordpress comprise a great deal of my day-to-day computing tools. None of these are anything like what Microsoft is developing for the desktop.

Down with the People: Finally, since I am a web user experience designer, it’s important that the tools I use allow me to understand and empathize with the tools my end users are using. Getting a Mac will surely decrease this empathy, but you know what? My Windows usage is so idiosyncratic that this empathy is probably minimal. Maybe I’m rationalizing, but again, I’ve gotten over this reason, too.

Why I am Switching

So clearly there are very few good reasons for me to stay with Windows, besides pure inertia. So why should I upend my entire computer life and adopt a whole new platform? That’s for next time, Why I am Switching: What I Expect and What I Fear.

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