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A Bag of Holding

The fundamental goal I have for a wallet via its design is that it prevents me from randomly collecting crap.

Years of folding leather wallets with myriad pockets and flaps all yielded precisely the same result: a Costanza-sized monstrosity that contained random crap that at one time I thought I needed, but eventually became useless clutter. This collection sat in my back pocket as a constant reminder of a tidying task I never did. Meanwhile, the massive collection of clutter ultimately destroys the wallet because no wallet is designed to perpetually hold everything.

The current wallet is perfect.

It’s perfect because:

1. There are zero moving parts. Whether it’s a flap or a mechanical money clip, moving parts fail.
2. There is limited capacity. The card sleeve barely allows me to hold eight card-shaped objects. Eight. This means that each time I attempt to keep a receipt I think I’ll need I have to fold it and slide it into the money clip. This means each time I handle my cash, I have to make a critical decision about the receipt — do I still need it? You’d be surprised by the half-life of items in your back pocket that you recently thought were important when you’re forced to look at them an hour later.
3. I’m not constantly stressing the architecture of the wallet attempting to contain everything. The current wallet has already lasted 4x as long as its predecessor.

It’s with this wallet design win that I embarked on a quest for comparable bag.

The Bag Requirements

My requirements for a bag start with those of the wallet, but with an important essential addition: my bag has multiple use cases. My bag needs to adapt to whatever journey I’m currently on, whether it’s a trip to work; a trip far, far away; or a trip where I’m sleeping in the dirt under the stars. A trip is either work or play, and since I work a lot more than I play, I chose to focus on work scenarios for my bag research.

I’ve heavily used two different types of bags over the past five years, and each has some win. To understand my initial requirements for a good bag, let’s quickly look at each.

A Christmas present, this Johnson & Murphy messenger bag was the first work bag I loved. I find it gorgeous. A large, comfortable shoulder strap and decent space made this my go-to bag for years. All that was missing was the addition of a Incase sleeve to give my MacBook a little cushioning and I was set.

In the past few years I began to travel more, and the travel exposed a core weakness: the bag doesn’t scale to far, far away. I found myself stuffing, shoving, and reorganizing headphones and power supplies in the bag, and while the magnet clasp works fine for a trip to work, when the bag is at capacity, it feels like it might pop open at any moment. I had a similar over the shoulder Tumi bag that was my workhorse for far, far away, but after sitting in a lot of airports, I’d seen a new development. Folks were wearing backpacks again.

I’m scarred by backpacks. My memory of backpacks was of these massive canvas-like bags full of immense and dense text books, crumbled paper, and a distinct smell of partially rotten peanut butter and jelly sandwiches. I remember constantly losing important papers in what was the seemingly infinite space contained within my bag, and I wasn’t interested in returning to that frustration.

However, after countless hours watching travelers sport backpacks, it was time to get past my scarring and give backpacks another try. Tom Bihn’s Smart Alec backpack was a chance to test this development.

After six months of steady use of my Bihn backpack, not only do I understand why people love them, I also better understand the complete set of questions and requirements I have for a good bag.

Does this bag make me look like a nerd? (Because I am.)

Bag religion is rampant. The only thing I’m looking forward to more than finishing this article is the crazy, foaming at the mouth bag nuts that are going to comment on this piece. My research is far less complete than in prior obsessive excursions, so bring it. I want to hear it. I’ve seen a lot of different bags, and my first requirement is that while I need my bag to be nerd-compliant, I don’t want it to scream “nerd”. This was part of my love affair with my messenger bag. It looked like I was part of the Pony Express when I was actually just a nerd hoofing my nerd crap hither and yon.

My bag needs to walk a delicate line between form and function. I need it to elegantly contain my various nerd crap, but I don’t need to broadcast to the world that, yes, not only am I sporting my nerd gear, I also have a back-up of the aforementioned gear because I’ve built in redundancy. That’s how I roll. I’m a nerd.

The messenger bag is a slight winner in this very subjective category. While the Smart Alec avoids most design disasters that remind me of JanSport-esque high school backpack monstrosities (straps, zippers, every kind of fabric everywhere, minimal pockets, and the color taupe), it makes less of a statement. It’s slightly more function than form. However, it is a better answer to the question…

Am I going to beat you through the security line?

The hands down collective best measure for any bag is its relationship to your situation in the security line at the airport. Let’s start with my mindset when I’m standing in line at security. I’m furious. Everyone’s furious. While we suspect the security line is essential, as we stand in that endless line, we know — we’re absolutely sure — there is a better way.

I’m fuming with this frustration when I finally get to the front of the line, but more importantly, I want to prove a point: I will now demonstrate to everyone the value of efficiency. Grab two trays, slip shoes off and put them in tray #1. Stuff wallet, iPhone, and boarding pass in shoes, belt off — NEXT TRAY — MacBook Air in second tray. Bag behind second tray, luggage behind that. And done. Why yes, I can do this and move the trays at the same time — WHY CAN’T YOU?

No where in the above process did you see “futzing with my bag and looking for shit”. In times of stress, a good bag demonstrates a couple of essential design points:

• Easy access to the items I commonly need. This means my computer is a single zipper away, but this ease of access does not mean the safety of these essentials is compromised. The Smart Alec is a clear winner here. In addition to the main compartment, there are two external side pockets that are large enough to hold the answers to most travel questions.
• Simply amazing zippers. My messenger bag has a magnet clasp and that works, but when I’m moving quickly, I’m wondering when this bag held together with a magnet is going to explode. When I close any pocket on my bag, I want to be left with the clear impression that the pocket is seriously closed.
• A minimum of crap hanging from the bag. Each strap is an opportunity to snag myself on a random piece of crap that I didn’t happen to see at the least opportune time. Traditional backpacks are the worst offenders when it comes to these straps. The designers seem to think I’m always mere seconds away from base jumping off a bridge where I need my backpack affixed to me in seven different ways. I don’t. I need two straps. That’s it.

However, I do want to know…

Can I go ninja?

The rule is: the further you are from your cave, there’s the exponential increase in the chance something will go wrong at the least opportune time. The best example of this is standing in front of 1,000 people who are expecting you to smoothly and expertly talk for the next hour and you’ve just discovered your MacBook doesn’t connect to the venue’s projector.

In my bag, I’m certain I have video connectors for most projectors on the planet. Furthermore, I have a universal power converter, a power supply, two presentation remotes, and sundry other essential white cables. All of these items are expertly collected in what Tom Bihn calls a Snake Charmer bag. This mesh bag is not only of a size that it can handle all of these items, it takes oddly shaped items such as power supplies and Jamboxes and molds them into an easily transportable rectangle that fits inside of my bag.

To allow for ninja-like moves, a good bag is designed to maintain state, which means:

1. There is a knowable set of intelligently aligned pockets of a size and shape that make sense. This is where my messenger bag fails. In order to maintain that Pony Express feel, the messenger bag design assumes that everything I’m going to lug about is roughly shaped like a stack of 8.5x11 paper. While the MacBook and the iPad are paper-shaped, I have essential items that aren’t square: delicate sunglasses, clumps of pens, and bizarrely shaped collapsible headphones. When I attempt to gear up for the long trip, it’s clear from the resulting lumpiness that the messenger bag was designed for a pleasing form and not useful function.

   The Smart Alec backpack not only has a sensible number of pockets, they are of a size that accounts for the fact that oddly shaped items follow me on my travels. More importantly…

2. In time of stress, the items are readily accessible, remain safe, and don’t shift around. I can’t predict when I need to go ninja. I don’t know when it’s absolutely essential that I have a pen ready to go in five seconds. When this moment does arrive, I don’t want to be digging feverishly around my bag, placing various items on the floor as I search the bottom of the bag where the small stuff has fallen. The Smart Alec backpack not only has a sensible number of pockets, they are readily accessible and not cavernous. At this moment I can tell you: right side external pocket is notebooks and the essential small crap bag (which I’ll explain in a moment), left external pocket is pens, mints, and playing cards, and the internal top pocket is safe and easily accessible for sunglasses, random small pieces of paper, a passport, and the occasional stash of hard candy.

All my stuff, readily accessibly at a moment’s notice — that’s pretty ninja. Still…

Is my bag smarter than I am?

Everything is exponentially and unnecessarily harder when you’re stressed, and it’s in these moments that you appreciate the design of a good bag. A well-maintained state allows me to go ninja, but knowing precisely where my stuff is safely located is just the first step. A well-designed bag is thinking for you when the last thing you’re doing is thinking. Some examples:

• Sub-bags. In addition to intelligent pocket size and positioning, Bihn pushes an idea to help me maintain state: sub-bags. For everyday trips, I have a single sub-bag that I’ll call “essential small crap”. Everything I’d normally lose or constantly be untangling is in a small bag that is transparent on one side, and which sits well contained precisely in the same pocket.
• An unexpected sense of space. This is a direct contradiction to my requirement that my bag prevents me from randomly collecting crap, but part of being ninja is the need to scale. I will randomly need to lug around a randomly shaped something from here to there and my preference is that my bag does this without fuss. The messenger bag fails here, especially on longer trips. I’m at max capacity on a long trip, which means I’m shoving newly acquired items in coat pockets or onto fellow travelers. As for the Smart Alec bag, I never felt I’ve filled it. Sure, I can lug your randomly shaped something… anywhere.
• Agility. My agility test is relatively simple: how many people are impacted/aware when I attempt to retrieve my MacBook while sitting in the middle seat? Any answer higher than one is too many. For the messenger bag, I first need to find the handle, which, given how it was shoved under the seat in front of me, is trickier than it needs to be. Then, I slide the bag out, lift the flap, unzip the Incase, and slide out the hardware. If you’re sitting on either side of me, you’re going to be well aware of this process because of my odd elbow gyrations.

  The backpack is shaped like a bullet. You slide the base easily under the seat in front of you, leaving the tip pointed directly at your feet. When I need something, the handle is at the tip of my toes, the zipper is easy to grab and works every time, and the Brain Cell holding the MacBook is right there. If you’re sitting next to me you’ll end up wondering, “When did he pull his computer out?” Whether it’s shoved into an overhead compartment, slid under a seat, or thrown in the back of a taxi, my bag needs to remain accessible and useful. This means I can get to it, and once I get to it, I can perform whatever action I intend without annoying every single person around me.

• Full range of motion. The defining aspects of a backpack are its most obvious — it’s on your back. After many years of single-strap messenger bags, I was shocked when I moved to the backpack and suddenly had two hands. A messenger bag does not full occupy one of your arms, but your shoulder is in a constant balancing dance with the bag to make sure it’s in the right place. With a backpack, this is a non-issue. When it’s on your back it’s gone and you’ve got a full range of two-handed ninja motion.

Through its design, a good bag makes me look smarter by giving me deft answers to most travel disasters, but I have one more request.

Can I take a bullet? Do I look good after I’ve taken a bullet?

As my bag accompanies me everywhere on the Planet Earth, it’s apt to encounter small random disasters. Briefly dragged on the asphalt, being drenched by half a cup of airplane coffee, or being unceremoniously thrown in the back of a cab. When these micro-disasters are going down, I need two things of my bag:

1. Everything in it needs to admirably survive and generally remain in the same location, and,
2. The disaster results in the bag acquiring additional character.

Sturdy is the word you’re thinking. Good solid craftsmanship. Yes, this is all true, but the art lies in building a bag that doesn’t look tired after the unexpected has occurred — the bag needs to look like it’s lived.

The messenger bag is a solid winner here. The bag has had the shit kicked out it, but it doesn’t look like it’s beaten, it looks worldly. The Bihn bag is well constructed out of impressive sounding materials such as ballistic nylon. It looks sturdy, it looks like it can take a bullet, but once the damage is done, I don’t know what story the damage will tell.

Efficient Disaster Management

When I stand up to go somewhere, the routine is precise. Right pocket, wallet. Left pocket, iPhone. Keys in hand, grab my bag and go. It’s this sort of workflow precision that allows me to stay cool when the unexpected occurs. My inner dialog during the situation is, Well, see, I’ve got my shit together, so even though this unpredictable thing is going down, I’m doing my part to support predictability.

Whether it’s a wallet or a bag, its design needs to encourage and support my irrational worldview that with the proper level of organization those disasters, large and small, are all manageable.

How Can I Help You?

Being computer literate means getting asked to help. I’m happy to help. I believe the less you fear your computer, phone, or tablet, the more you’ll get out of it, so, absolutely, How I can help you?

However, this free tech support does come at a cost. I have a system for evaluating a problem which is accompanied by colorful inner monologue. The following flowchart explains both the details of how I triage a problem, how I might fix it, and how and why I’m likely to swear while I’m helping.

Download the larger version.

Why?

Early in the design discussion for the logo for the latest Rands in Repose charity t-shirt, Robert Padbury responded to my early design feedback: “You know, I realized something when I was thinking about this the other day - People don’t really have more than the following three responses to a design:

1. It’s awesome.
2. It sucks.
3. Apathy.”

This short list of responses captured me with their lack of subtlety. Three bullets effectively describe the majority of opinions people have about topics that often deserve more consideration. While Robert’s eventual point was different, his observation serves as a starting point for understanding why I’m once again offering a t-shirt supporting a literacy charity.

As with all other prior shirts, all of the profits go to First Book, a charity focused on promoting children’s literacy. The reason I continue to choose this charity is simple: I think the more people take the time to read increases the likelihood that they can build a defensible opinion.

Having a defensible opinion takes work. There is infinite information out there and that means you need to pick and choose the topics where you want to stop and ask, “Wait… why?” I’ll explain via a creepy story.

Back before there was a publicly available Internet, a doctor told my mother that smoking would keep the baby’s birth weight down. Funny thing is, it’s true. The unfunny thing is that low birth weight babies are at an increased risk for serious health problems and lasting disabilities. The decidedly unfunny thing remains — it was her doctor who told my mother this “good news”.

History is full of lies and ignorance propagated by people who’ve put their trust in the ideals of allegedly qualified others. Now, as we live in a world divided by opinions acquired via Twitter, it’s never been easier grab onto a clever 140-character quip and assume it’s the truth. The fires of ignorance burn wildly on these acts of intellectual laziness.

Having an opinion takes work. It means stopping in your tracks and staring conventional wisdom in the face and asking it to explain itself. It means drilling deeper than the conventionally polarizing opinions that a topic is simply awesome, it totally sucks, or it’s completely irrelevant to you. Chances are, it’s a little bit of all three, but that type of ambiguity is mentally exhausting, right? Can’t we just love or hate? It’s so much easier to yell when it’s right versus wrong or us versus them.

Having an opinion means starting to explore in Wikipedia as a means of defining and refining your curiosity, but not trusting that it’s true. It means researching and building an intellectual map around a question. It means having the confidence and the courage to open a book, find the facts, and working to build a complex and defensible opinion so you can personally answer the question: “Why?”

And I think it’s a habit we want to encourage as early as possible.

The third version of the Rands charity shirt has a new purchase option. You can either purchase the lovely red shirt or the limited edition gun metal version, which also includes a set of customized Field Notes. The clingy bamboo stylings of previous shirts are gone and replaced with American Apparel’s finest short-sleeve cotton t-shirt. Again, all proceeds of both shirts go to First Book.

I’d like to thank Robert Padbury and Jim Coudal for their generous donations to this effort. They are both awesome and now you know why.

Building Serendipity

Blake looks tired. He’s sitting in the food court at O’Hare Terminal 1. He’s halfway through a beer and the jokes are coming out, but they’re a little labored. Blake is tired.

Blake’s tired because Blake goes to a lot of conferences. Earlier in the conversation, he was explaining the next month of travel and I lost track of the number of conferences he was attending somewhere between Peru and Brazil. I feel like I attend a decent number of conferences over the course of the year, but Blake’s list quickly demonstrates that I’m a conference rookie.

Still, I know why Blake is tired.

That One Person

I have exactly one goal when I attend a conference. Through some bizarre and unpredictable sequence of events, I’m going to meet that one person I absolutely need to know. Who they are, what they’re building, or what they’ve done — it’s mind-blowing shit that, once identified, forever alters my perspective. In hindsight, after each conference is complete, it’s obvious who this person is because I can’t stop fucking talking about them. Before the conference this person is a mystery and there is no reliable way to predict who they might be.

My evolving experiences with conferences over the past two decades both conveniently enable documenting the three types of conferences out there, as well as my strategy for building the possibility of serendipitously meeting that person who will rock my world.

The Everybody Conference

Comdex was my introduction to both conferences and Las Vegas. In my late teens, my Dad was making a tidy profit building clone PCs, and Comdex was the place to see the latest developers in the PC world. I remember when Bill Gates got up on stage and showed a new feature in Microsoft Word that allowed you to visually draw tables in a document. Times were simpler then.

The Everybody Conferences are defined by their hugeness. Present day WWDC, SXSW, and JavaOne are similar beasts where each and every one of the faithful gathers to drink deeply of the Kool-aid. The food sucks, presentation quality varies wildly, and you seem to constantly be in line, but everyone is there and how often do you get an opportunity to hang with everyone?

For me, the Everybody Conference is a stressful affair. I am uncomfortable in large crowds and standing in lines drives me insane. However, I appreciate that both lines and crowds are significant opportunities for serendipity, so where’s the middle ground?

I’ve refined the compromise strategy after many years at SXSW: find a conveniently located bar near where everyone is stumbling, invite two close friends and buy them a lot of booze, and then tell anyone who might care where you are. This event comfortably starts with just the three of you and becomes even more comfortable as the booze begins to flow. Serendipity is encouraged both by being in a public location where folks randomly show up as well as via your invite to those who might care.

At SXSW, I rarely attend sponsored events (lines), I rarely attend talks (panels? really?), and while I might wander the conference hallway a few times, my strategy of hiding in plain sight allows me to balance avoiding the hugeness while still encouraging serendipity.

The Specific Agenda Conference

The Specific Agenda conference is a smaller affair and has a specific theme, whether it is technology or audience. There is delightfully less pomp and circumstance with the Specific Agenda conference, but more importantly, there are fewer people. Whew.

A smaller conference is more palatable to me not only because the horde isn’t there, but because the conference can be comprehended. I can get both the entire theme and audience in my head, which, as a nerd, gives me the illusion of predictability and knowability. However, the decrease in population size means more aggressive steps are necessary to encourage serendipity. I can’t hide in a bar and tweet my location: I need to be proactive.

The strategy at the Specific Agenda Conference is: attend everything. After I’ve arrived, checked in, and am sitting in the hotel room reviewing the conference, I invariably find an event and think “lame”. I still go. Yeah, I don’t need a job, but I’ll check out the job fair. Yeah, there’s an awkward corporate speaker whose presentation is more advertising than content — I go to that as well. I might walk out after three minutes, but I still show up because at a smaller conference I want to know the Story.

Because of its size, the Specific Agenda conference builds a discernible shared story. It starts when the keynote speaker is simply awful and you lean over to a stranger and ask, “Is he that bad?” In a moment, the stranger becomes slightly less strange when she nods, “Yes, he’s really awful. And he’s my boyfriend.”

Oh.

There is now one less stranger at the conference and the first page of the Story, which is titled, “Wherein I make a new friend by ripping on their boyfriend’s crap keynote” and it’s a great story that everyone has a version of because they’re all sitting there with their own experience of the horrific keynote.

By including myself in the majority of the Specific Agenda Conference, I see what everyone else sees, and we collectively build a Story that introduces and intertwines us. I can think back to every Specific Agenda conference and feel the Story that was built. There was that one in Montreal where at 2am we ended up in a line in subzero weather waiting to eat poutine. Yeah, I was in a line. You know why? Because I knew I was in the middle of a great Story and great Stories are great fodder for serendipity.

The Welcome to Our Home Conference

The final conference is just a variant of the Specific Agenda conference, but I’m calling it out because this conference is one built with serendipity in mind. To date, I’ve only attended two Welcome to Our Home conferences: Webstock (three times) and Funconf (twice).

This conference is what it’s called: an invitation into someone’s home. It has some technology, design, or open source theme of some sort, but that’s just there to get your attention. The real intent of this conference is building serendipity, and they do in three increasingly important ways:

Quality of speakers. Each year, Wellington, New Zealand’s Webstock shocks me with their speakers. Go look now. Yeah, you’d go for just half of those folks. Dublin, Ireland’s Funconf is less forthcoming with their speakers, but that’s because they sell out tickets simply on the strength of word-of-mouth from the first conference, which included a bevy of fascinating speakers.

The Venue. Webstock is held in Wellington’s town hall, which looks like this:

This Funconf was held in a castle and that looks like this:

The venues for both conferences go out of their way to make you feel like you’re not at a conference, but rather hanging with your friends, well, in a castle. More on this aspect in a moment.

The Organizers. In my opinion, the defining characteristic of the Welcome to Our Home conference is the organizers. Whether it’s Webstock’s Natasha Lampard and Mike Brown or Funconf’s Paul Campbell and Eamon Leonard, each conference is a reflection of the care of these organizers. I just returned from my second Funconf and I know that it was held in a castle because of Paul, and I know there was a clown, a DeLorean, a llama, and a donkey in the courtyard thanks to Eamon. You’re right — it doesn’t make sense — but that’s because you weren’t there and you weren’t a part of the Story.

There is very little strategy in play when it comes to the conference. They tend to be small enough that I don’t hide and there is rarely an event I’m not tripping over myself to attend. The Story builds itself with little effort on my part and there’s serendipity everywhere.

Welcome to Our Home

I’m eating an awful ham and cheese sandwich and drinking a Sam Adams when I ask Blake what his favorite part of Funconf was, and he gives the same answer everybody does about any conference: “Well, it’s the people, right?”

Blake knows what I know. Whether it’s Everybody, A Specific Agenda, or A Home, a conference is defined by the people. And that’s why I’m a little a jealous of Blake. I know why he’s tired. He was up until 6am drinking with the CTO of Amazon in front of the fire… in a castle.

And that’s a great story.

The Anatomy of a Notification

In an otherwise elegant and well-integrated operating system, the notifications user interface in iOS 4.x feels like a wart — a tacked-on afterthought that offers a bare minimum of usefulness.

Competitors have jumped all over this weakness. An early Microsoft Windows Phone ad implies a strategic notifications deficiency by showing users glued to their iPhones… because of the platform’s alleged inability to give users aggregate, at-a-glance updates. The ads’ strange reasoning ignores the idea that iPhone users might be glued to their phones not due to the fact that they didn’t know something occurred, but because the phone is so damned useful.

The Microsoft ad while entertaining is ultimately confusing and contradictory. It implies that you’re going to miss something important while you stare at your iPhone, i.e. the entire point of an elegant notification system is that you miss nothing.

An elegant notification system and application will come to iOS — likely this week. Apple hired the designer of WebOS’s notification system a year ago in May, and that’s good news because there’s a ever-growing mountain of evidence that notifications are a big deal.

The Evolution of Notifications

At the tail end of Web 1.0, Google busily indexed the entire web for us and gave us a reliable, useful, and easy way to find content. In a world previously governed by the Dewey Decimal System, Google was a goddamned miracle. In 7th grade I was asked to write a report on clepsydras. I had to wait a week until my Mom drove me to the library just to figure out that a clepsydra was a water clock. A week. Can you imagine a world where you couldn’t curl up on your couch eating Doritos and cottage cheese and simply click a link on your iPad to learn everything about David Hasselhoff?

I can’t.

The Pandora’s Box opened by the arrival of the Internet is that we are now aware that all the information is out there, and it’s readily available, but we lack the time to surf its infinite enormity. You don’t have time for everything. In fact, you don’t have much time for most of the what’s on the Internet because you’re just one person with strange eating habits. You pick and choose. Yes, I will read Suck. Yes, Kottke appears capable of finding content I care about. You delegate the filtering of the Internet to trusted others and you were grateful when RSS and RSS readers showed up because the technology gave you one-stop shopping for your then inefficient content consumption.

RSS represented a leap forward. You now had a means of aggregating and reading the content of your trusted others at your convenience. And more importantly, when that content was updated, you received a handy notification that something had changed. Oh look, 23 new articles. We were content with this standard, but then something happened. RSS was killed.

It wasn’t a deliberate hit. There was an information explosion and RSS was collateral damage. The content you cared about grew exponentially. It wasn’t just blog articles, it was tweets, likes, status updates, new followers — an endless list of micro-information and RSS hasn’t evolved. The likes of Twitter and Facebook tried to keep RSS around, but in a world where advertising is king, a standard that provides a facility for consuming content and skirting ads doesn’t make business sense. RSS is still sprinkled around these services, but it’s hard to find and when it breaks no one seems to care to fix it.

RSS lost.

In a daily information consumption routine, RSS has effectively been replaced by different systems of notifications. While notifications are neither a functional replacement nor a standard, they’re a timely and important idea. If RSS is a standard for structured document-based pulls, notifications thrive as standards-free, chaotic, atomic pushes… and we need to wrangle them.

The Anatomy of a Notification

Before I explain how notifications are slowly taking over your life, let’s agree to a definition. To me a notification is a small piece of information that is:

• Human Consumable: built for a human to assess, not for a machine.
• Brief & Relevant: the content inside of a notification takes only a smidge of your attention in order to assess a next step.
• Portable: a notification stands on its own; you need no additional external application to assess it. They stand outside of the data or application they might represent.
• Disposable: if for some reason the notification doesn’t get to you, you have an obvious means of recourse to find the data.
• Timely: the usefulness of a notification decays as a function of time. Late notification arrival incites nerd rage.

Try the definition on:

• Is a tweet a notification? Yes, unless it’s a tweet that’s part of a continuing conversation chain.
• Is your phone ringing a notification? Yes, as long as you have an answering system for when you’re not there, thus making the notification disposable.
• Is an email a notification? No, an email usually fails to meet all the criteria in that it usually isn’t brief, it often heavily depends on the context of other emails, isn’t always disposable, and, well, sometimes an email isn’t coherent even to humans. However, a Growl notification containing the subject line of an email is totally a notification.
• Is an SMS a notification? How about an instant message? Like a tweet, only the first message in a chain is a notification. The first message is your alert: “Should I converse with this person right now on this particular topic? Yes or no.”

Make sense? Think I’ve gone around the bend over-thinking notifications? Keep reading.

An Economy of Notifications

The Internet is a flurry of notifications. Likes, updates, points, favorites, and retweet buttons beg everyone to click them to capture the micro-opinion of the moment. It’s no longer a badge of honor to have a blog; the question is: how much karma have you amassed on Hacker News?

It’s a goddamned sea of notifications. I know this because of the amount of time I’ve spent hacking together a notification strategy. I’m regularly updating mail rules to account for the various notifications emitted from Twitter, Quora, Facebook, and the like. It’s a growing pile of work and therein lies both a problem and an opportunity.

The problem with notifications is that the cost to create them is close to zero — just hit that Like button or go ahead and click that retweet button. As their creation cost approaches zero, notifications rapidly become spam-like as the noise of their quantity masks the quality of their signal. But we learned our lesson with spam. We knew what happened when we lost control of our inboxes and spent our time sorting through the useless noise searching for the signal. We learned how to curate. Curation is social-media-douche-speak for “deliberately choosing and pruning the content you care about” and I think part of the next Internet is curation at scale thanks to notifications.

I Want To Know What I Want to Know When I Want To Know It

With social media companies having little incentive to open up their notification streams, we need new leverage. We need a platform to insist on the collection, organization, and management of notifications, and that’s the platform sitting in your back pocket. Open or closed, iOS and Android are in a unique position to standardize notifications in order to keep them useful.

As Microsoft clumsily demonstrated in their ad, a mobile interface is an interface for a moment. The goal isn’t deep consideration of a thing. The goal is instant assessment of, well, everything. When I pull my phone out of my pocket, I want to answer a fairly impossible question: “How has everything I care about in the online universe changed since I last checked?”

Tall order. And one that can partly be conquered by notifications with a feature set that is defined by the definition of notifications:

• Human Consumable: We need a centralized, highly visible and beautiful place that contains all notifications for the apps and services we care about. The logical place is the first screen you see when you launch your phone.
• Brief & Relevant: The use case for this screen is: “How quickly can I pull the phone out of my pocket and assess what the hell is going on?” The faster, the better. Preferably before I crash the car.
• Portable: The interface must be the interface for all notifications. The triage experience is exactly the same whether I’m scrubbing Facebook, Instagram, or Twitter. It’s cool if drilling down into a notification requires automatically jumping to a different app, but enough information must be presented to allow me to make the decision of “Should I proceed?”
• Disposable: If a long period of time passes between when I check in, the triage experience is the same — tell me what is changing right now. I don’t care what happened yesterday. Old notifications are meaningless to me. I have other elegant means of assessing the changes of the week or month.
• Timely: While notifications are disposable, their timely arrival is essential. The real-time push aspects are fully aligned with my attention deficiency disorders.

Lastly, this entire system needs governance by a well-designed notification application. iOS 4 already has a system-level notification system, but the presence and success of applications like Boxcar are a clear sign of the functional deficiencies of the system. We need a notification system that accounts for the fact we’re constantly signing up for new information, but don’t have the time or the tools to pay attention to it. We need a tool that allows us to adjust the level of detail of the data we receive to align with the level of attention we have to give it.

RSS Didn’t Lose

I realize a comparison between RSS and notifications is not a fair one. I’m effectively comparing a family of web feed formats designed around slowly changing content with an application and a system service. But where the standards and the application intersect is the use case: tell me what has changed.

Notifications are the smallest bit of disposable, human-readable information that conveys something you care about. Their real-time nature gives notifications an immediate sense of importance. Well, my ass is vibrating, so it must be important.

If you want to rip on notifications, you can angrily wave your finger at the folks who believe discovering a thing has anything to do with understanding it. Notifications reinforce our addiction to the now. That vibrating ass of yours gives you the false impression that you know something, but all you really know is that something is different. The value of information does not decay as fast as the immediacy of the notification would have you believe.

Anyone who’s ever lost three hours to “choose your own adventure” on Wikipeda knows that infovores want to know what they want to know when they want to know it, but that “it” is never fully covered by notifications. My nighttime routine always involves RSS. I curl up around my iPad, fire up Reeder, and see where the Internet takes me because sometimes we need to go deep.

[Post-WWDC Update] Just about everything I wanted fixed in notifications was addressed with iOS 5. While I had limited hands-on time with the feature set, notifications are now a first class information citizen throughout the OS. Notifications are easily consumable regardless of where you are in the OS and equally easy to act upon. You’re able to set the visual intrusiveness of a notification (say, if you love the old modal dialog for important notifications) on an app-by-app basis - I’ll use that.

Is Boxcar dead? I don’t think so. Notification Center replaces Boxcar’s aggregation functionally, but I never used that feature. What’s useful to me in Boxcar is the ability to build customized notifications on top of other services. My gut says that is Boxcar’s sweet spot and notifications in iOS 5 will give those Boxcar notifications a place to shine.

Is this notifications UI way similar to Android? Yup. Here’s the rule: you copy great ideas — that’s how we know they’re great.

Summer Intern Field Guide

Dear Summer Interns: Your stock is up — like way up.

Ten years ago when I was hiring interns at the mothership, my incredibly flawed and shortsighted policy was to hire as many as they’d let me, dole ‘em out to the teams that screamed the loudest, and see what happened. There were successes, we found some good people, but my memory is shoddy because I just wasn’t paying that much attention. For shame.

Fast forward to the present day and the internship landscape has drastically changed in the Silicon Valley. Competition for interns is fierce for a couple of old reasons and an emerging new one.

• Internships remain a low-risk way for both candidate and company to evaluate each other in a short time frame and with a deadline.
• We, the hiring companies, have an ever-increasing crapload of work to do, which provides an excellent crucible for this evaluation. And, finally,
• In the last decade, interns have continued to arrive with an ever-increasing pre-existing skill set that allows them to hit the ground running.

That said, even with everyone cheering for you, you can still screw up your internship - easily.

The following guide walks you through what I’ve learned are essential moves for your summer internship.

A Swell Gig

Whether you’ve landed a summer internship, co-op position, or contracting gig, the defining characteristic is the tick-tick-tick of time. On the day you start you know the day you’re leaving. Given this clear deadline, there are two things I want you to do before you set foot in the gig.

First, pick one thing you want to learn. You’re likely starting this whole process with the idyllic perspective that, “Golly, it’s swell they gave me a gig”. This is factually true, but I prefer the perspective: I am choosing to work with these fine people because they have a thing to teach me. Every job I’ve loved shares the same characteristic: I’m learning from people I respect.

Before you show up and are overwhelmed with the inevitable flood of projects, people, and personalities, you need to make a choice about what you want to learn:

1. I want to learn how to become a better developer.
2. I want to know how to build a team.
3. I want to learn how to ship products.

Don’t stress about this - pick two if you want. Just choose and understand the choice is not written in stone. In fact, careful adherence to the advice below pretty much guarantees that you’re going to change your learning goal a couple of times. The absence of this goal is a great way to start your summer with the aimless and listless perspective of: “What are they going to bring me?” Goal in hand, you start by asking, “How am I going to find what I need to learn?”

While you figure this out, you also need to figure out what the company is bringing to the table and you can start to deduce this investment in a couple of ways.

How much communication are you getting from the company leading up to the internship? How quickly are you getting answers to questions? Do you know whom you’ll be reporting to? Is it clear what you’re going to be doing before you show up? Are you getting schwag? Are you getting homework? Are they building excitement?

This assessment doesn’t stop on Day 1. You need to keep watching: Are you getting a script the moment you walk in the door? Is it obvious who is in charge? Are you sitting there staring at your screen without a machine wondering what to do on day 2? Uh-oh. Is it Friday and you have no idea where the week went? Good.

I’m not suggesting that a lack of engagement by your employer guarantees a crappy internship, but it does change your opening strategy. A well-constructed internship program is about creating opportunity for interns to both deliberately and randomly kick ass, and the sooner you detect the quality and depth of the program the sooner you’ll know how much opportunity you’ll need to create on your own.

Whether the early signs are positive or negative, you’d better get started because: You’re in a hurry. Again, an internship is defined by time. For a summer internship, you have 90 days. That’s it. It’s going to feel like forever when you arrive, but in my experience it’s usually barely enough time to really figure out whom you’re working with, what they’re working on, and what they care about. Your internship has an expiration date and you need to accelerate the assimilation process, and that means understanding that…

Products are Built by People

My second summer working in high tech was at Borland and they were deep into the first version of Paradox for Windows. I arrived in the middle of a push towards Alpha, which meant I got a cursory handshake, a computer, an office, and the well crafted, detailed instruction to “Find bugs”.

If you believe my program assessment advice, I should have rated myself a solid “screwed”. No initial support, no investment, no clear direction. Thing was, it was the best damned internship ever. These people were in a hurry — they didn’t have time to explain the intricacies of the product development process to me because they were living and breathing it. They had no problem grabbing me for a design meeting halfway through my second day and throwing me squarely in the deep end.

“You - new guy - we need to know if this new Create Table dialog is crap and we need to know by 3pm. Got it? Good?”

Create what table? In what part of the product? What does crap mean anyway?

Devlin, the lead QA guy, who wore the hair and attire of someone who hadn’t slept in weeks, grabbed me as we walked out: “I’ll help you install the latest build. You need to get the bug tracking system up and running while I’m doing that and figure it out. I’ll walk you through the three create workflows. If you find three bad bugs, it’s crap.”

Software built in the real world has nothing to do with what they teach you in college. There are no courses entitled:

• The Mountain Dew-Fueled Development Cycle
• The Myth and Madness of Zero Bugs
• Done is a State of Mind.

There is plenty of value in university, but until you build a complex product, beginning to end, with a team, you have little idea how product is built. An internship provides essential real-time lessons to understand both how a product is built and who is building it. Start with:

Finding a mentor. Most intern programs take the time to assign a person in the trenches who isn’t your boss and who is responsible for your daily care and feeding. A good mentor is someone you see regularly, and neither of you feel like these visits are a chore. If you’re getting the chore vibe, you need to find another mentor, which ties in with another assignment…

Finding a cohort. If a mentor’s job is to answer questions, a cohort’s job is to find more questions with you. Your cohort is your invaluable second set of eyeballs. They are likely on the same schedule as you and share an interest in what you want to learn. You can go it alone during an internship, but it’s inefficient. You’re going to screw up; you’re going to waste time chasing something useless, and a good cohort will call bullshit on these activities faster than your boss or your mentor because they share your interest. More importantly, your cohort identification and selection might be your first professional attempt to build a team. Wondering where they are? How about…

Talking to everyone. As an engineer, you may have anti-social nerd tendencies. You might be supported by a phenomenal intern program that accounts for your every need. But if you’re heads down simply fixing bugs, you’re not learning how to build product. You need to attend every single intern event where you are exposed to as many people as possible. You need to frequently stand up, walk around, and investigate what each group does, how they fit together, and how they each contribute to the product. And you do that by…

Incessantly asking questions. I understand that it looks like everyone is darting about with purpose, and I know that you think your question about security certificates is insipid, but we want you to ask. We want you to be unblocked so that you can get to the meat of building things. More importantly, we learn both about you and ourselves via your questions. We see our products and our processes in a fresh light through your eyes. The rule is: the sooner you ask, the faster you’ll know.

Understanding that you have little time for drama. You might not know what office politics look or sound like, so here’s a familiar scenario: remember those uncomfortable cliques that showed up in high school? Those folks walking around like they hit the popularity lottery? When someone walks by and you sense the familiar twinge of douchiness, find a reason to walk away. It’s not a guarantee, but there’s a good chance there are politicians, malcontents, and jaded curmudgeons somewhere in your company, and they are recruiting for their cause because they need cynicism to feed their agenda. All you will discover by hanging with these folks is the disenfranchised sub-culture of bitching and moaning, and while it is worth noting that this culture has been allowed to exist in your company, it is not worth your time.

Your Goal is Not an Offer

And it’s suddenly over. It’s late August and you’re two weeks from returning to school. Went faster than expected, right? So, what’d you do?

“Well, it was pretty cool. I worked on the search infrastructure for this analysis tool. I learned a bunch about Lucene, and…”

No, that’s not what I’m asking. What did you do?

Your reputation with your team and the company will be defined by something you cannot predict. If you diligently complete the work assigned to you and attend all the social events, you will have a fine internship, but the flavor of this internship is vanilla, and vanilla is reliably boring.

What is the thing you built that:

• You initiated and completed
• Supported your learning goals
• Included your mentor and cohort, and
• Unexpectedly kicked ass?

An offer at the end of a summer is a happy by-product of a successful internship, but your goal is experience. We’d be happy if you joined the crew and that might be a good move, but we know your stock is way up.

What has changed in the last decade is that everything you need to build your own company is actually just a keystroke away whether it’s tools, infrastructure, or cohorts. This ready availability of resources allows for the one of my favorite discoveries when reading a resume: “Last quarter, in my spare time, I founded a company”.

Never before has there been so much potential for bright people, college degree or not, to build something that might change the world, and your internship is one way to learn how we construct our teams and our products, not so you can replicate our success, but you can define your own.

The Noise

It started that morning when you actually had time to go to your favorite coffee shop on that Wednesday morning. You, like many of us, had a bunch of time off for Christmas, so you decided, “I never go to that coffee shop and it’s one of my favorite places to think. Fuck it, I’m going.”

You threw on your favorite sweater — that one with the holes in the elbows — and your blue baseball hat. You ignored the urge to invite a co-conspirator on this visit. You just wanted an uncomplicated, unencumbered, easy trip to the coffee shop.

You arrived, grabbed a cup of black coffee, found a small, round, wooden table with two chairs, and sat down amidst the chorus of dozens of coffee drinkers discussing topics you could hear, but not understand.

With your hands firmly around your coffee cup, you stared around the room and your mind drifted. I love this place. All coffee shops should be built of dark wood. And all furniture. In fact, I need a new desk… made out of dark wood because… I hate my job.

There it is. It’s certainly a topic that’s been on your mind, but it took a solo trip to the coffee shop during a post-Christmas decompression period for you to actually hear what was important to you. More importantly, it sticks.

During the drive home you realize: I hate my job because, while I’m busy, I haven’t learned a thing in the last six months. That night over dinner, you find yourself shaking your finger at your best friend: Shame on me, six months of uselessness and that changes — now.

Frustration has blossomed into the beginnings of strategic resolution and the reason that happens is a lack of Noise.

The Noise

The Noise wants you to believe it’s Signal. The Noise is things you need to do, and they are approachable, knowable, and accomplishable things. You do them — one by one — and mentally pat yourself on the back as you finish them because you have a sense of moving forward.

The Noise surrounds you. People walk in your office with their Noise and they write it on your whiteboard. You nod and agree, “Why, indeed yes, that’s noisy” and they leave comforted — thinking your agreement was somehow progress.

And that’s the greatest lie of the Noise. The idea that listening and reacting to the Noise is significant progress. Yes, these small bits of work we do all day are essential to getting things done, but go back to your last big vacation. After the first three days of decompression, when you were sitting in that hammock with a glass of red wine, under that oak tree that is older than anyone you know… tell me what you were thinking about. Was it the 27 bugs you left in an unverified state, or was it the epiphany that in the first three decades of your life you haven’t come close to building something as impressive as this damned oak tree?

The Noise wants you to believe it’s Signal and its omnipresence in your life slowly and deviously convinces you that the Noise is important. But all listening to the Noise does is deafen you to the things that are important.

Taking Time to Think

You return bright and shiny from long vacations because you’ve no longer been dulled by the Noise. Your job once you’ve returned is to maintain that shininess, which is hard… the Noise is everywhere.

This is why I believe you have to work to make a 1:1 a conversation and not a status report. This is why you’ve established a regular communication cadence with your team, but don’t panic when that cadence is altered. This is why you force yourself outside of the building where you seek unbiased external perspectives willing to not only explain their part of the world, but also hold a mirror up to yours. And this is why I believe you get up and radically change your gig every three years.

These habits are designed to create unexpected moments with Signal. Each moment with Signal is a moment that you’re killing the Noise and they exist so you remember what it feels like to care rather than just do.

Interview: Marco Arment

On my list of horrendously bungled acquisitions, I put Delicious near the top. Since its acquisition by Yahoo in 2005, the biggest user-facing change to the site was a visual refresh in 2008. Even with this rampant feature stagnation, I’d stuck with the site because it solved a daily need for me — bookmarks anywhere.

Yahoo’s strategic negligence is mind-boggling. In a world of exponentially increasing information, coupled with increasingly different ways of accessing it, the idea of investing in a social service that tells you precisely what your users care about strikes me as a no-brainer.

Fortunately, nature abhors a vacuum and Marco Arment’s Instapaper has deftly stepped in to replace Delicious. I spoke with Marco via email to understand the origins of Instapaper, the valuable lessons he took from his first company — Tumblr — and how he manages one of web’s most useful sites as a one-man shop.

RANDS: Where did the idea for Instapaper originate and how long until you had a usable product?

MARCO: In the fall of 2007, I had just switched to the iPhone, and I had a long train commute every day. I never knew what to read on the train, but I’d find stuff all day at work that I didn’t have time to read, so I made Instapaper as a simple, one-click link-saving service for myself to time-shift links from the work day to my train commute.

The original web app took only a single night to write. It was usable, but it was very simple.

Over the next couple of months, I added a few useful features, most notably the “text” mode to strip articles down to iPhone-formatted text. This was so the EDGE-only original iPhone could download them quickly and keep more tabs in RAM without needing to reload them when I was potentially underground and offline.

When did you know you had something viable on your hands?

I just used it myself and didn’t tell anyone for a few months. I then showed it to a couple of friends. After a week of using it, they were already raving that it was amazing and it changed the way they read, so I gave it a few nights of polish and posted a simple link to it on my blog.

Within days, it had thousands of users and was getting widespread acclaim. I had no idea it would get so big so quickly.

What’s your favorite stat or fact regarding Instapaper?

Most people assume that online readers primarily view a small number of big-name sites. Nearly everyone who guesses at Instapaper’s top-saved-domain list and its proportions is wrong.

The most-saved site is usually The New York Times, The Guardian, or another major traditional newspaper. But it’s only about 2% of all saved articles. The top 10 saved domains are only about 11% of saved articles.

You’re a one-man shop and are, among other things, developer, support, and operations — how do you pull that off?

A lot of coffee and Phish.

Were there design decisions you made early on in order to manage that? What were they?

Absolutely.

The biggest design decision I’ve made is more of a continuous philosophy: do as few extremely time-consuming features as possible. As a result, Instapaper is a collection of a bunch of very easy things and only a handful of semi-hard things.

This philosophy sounds simple, but it isn’t: geeks like us are always tempted to implement very complex, never-ending features because they’re academically or algorithmically interesting, or because they can add massive value if done well, such as speech or handwriting recognition, recommendation engines, or natural-language processing.

These features — often very easy for people but very hard for computers — often produce mediocre-at-best results, are never truly finished, and usually require massive time investments to achieve incremental progress with diminishing returns.

If a one-person company is going to build a product, it can’t have any of those huge time-sink features. At most, I can afford to have one or two components of moderate complexity, such as the HTML-to-body-text parser and the Kindle-format writer. But even those are barely worth the time that I put into them.

What were the biggest lessons you took from Tumblr that made the design, development, or deployment of Instapaper easier?

Tumblr didn’t have a dedicated server administrator until a few years into its life, so I had to be our de facto server administrator in addition to my primary developer role from Tumblr’s start until we had 48 servers handling about 5,000 requests per second.

Since that’s a sizable infrastructure, but we had very little time to devote to maintaining it, I had to choose mature, stable technologies with great tools and very low administration needs. And I built Instapaper on the same technology: PHP 5 with a custom high-performance MVC framework, MySQL, Memcache, Apache, and CentOS, on high-end dedicated hardware.

This proved invaluable to both Tumblr and Instapaper, since I don’t need to deal with webserver processes crashing, corrupted databases, or any serious platform issues. All of these tools are used by many other companies with deployments much larger than these, so nearly all of the bugs get worked out long before they get a chance to affect us.

The result of all of this platform conservatism is that I can spend my time improving the product in meaningful ways instead of fighting with my server software.

What part of Instapaper’s infrastructure are you most proud of?

The bookmarklet has a mechanism to save pages from sites that require logins for full content, such as the Wall Street Journal and Harper’s, by sending a copy of the page’s HTML from the customer’s browser to the server. It’s like automating the “Save as…” menu item: if you have your own account for these sites and can see the page in your browser, you can save it to Instapaper.

The way it does this is ridiculous: instead of calling a simple GET request to save the page, since an entire page’s contents would quickly overrun any URL-length limits in the stack, it injects a FORM with a POST action and populates a hidden value with the page contents.

But form-data requests from browsers aren’t Gzip-compressed, so the resulting data is huge and needs to be sent over people’s (often slow, often mobile) upstream connections. So I found an open-source DEFLATE implementation in Javascript — really — and the bookmarklet compresses the page data right there in the browser before sending it.

The whole procedure is hideously complex, but works incredibly well.

Instapaper integration seems ubiquitous in any information consumption application that’s been released in the last year - how did that start?

This started as a fortunate side effect of having a few influential developers who were fans of Instapaper, most notably Loren Brichter (Tweetie, now Twitter), Craig Hockenberry (Twitterrific), and Brent Simmons (NetNewsWire), who integrated send-to-Instapaper features into their respective products a long time ago. And since the Twitter and RSS client markets are so competitive and innovate so rapidly, many other developers quickly followed suit.

Now, it’s almost always a highly requested feature for new content-finding and content-consumption apps, especially on iOS. I’m just honored and humbled that it has become this widespread.

My impression is your feature development process is very iterative — do you start with something that you want yourself and then slowly develop for your users? Does it work? How do you know when you’re done?

That’s correct. I don’t plan specific, major releases very often — I just incrementally build on the product in development, test features on myself for a while, cancel those that don’t work, and roll up the successful ones into a release every few months.

Generally, I know I’m done because as I’m testing the migration from the current in-store version to the new version, I cringe at how bad the in-store version is relative to my shiny new development copy. I think, “I can’t believe *that* is what customers are using right now, when they could be using *this*.”

That’s when I freeze new features, fix any known bugs, polish any rough edges, begin final testing, and prepare to issue the release.

What productivity tip have you discovered that now you can’t live without?

Keep a to-do list.

A real one. One that you actually use and update throughout the day. It doesn’t need to be fancy, like the getting-things-done task managers — I use TaskPaper, which is essentially a text editor with optimized syntax highlighting for to-do lists, against a text file on Dropbox.

I’ve never been a note-taker. In high school, I was that smartass kid who never had any notebooks or anything on his desk in class. Just a blank desk to slowly fall asleep on. I thought I could just keep track of everything in my head, which is true in high school if you’re a smartass slacker, but doesn’t work very well after that.

If a task isn’t written down in a list or set to alert me in iCal, it’s gone. Forgotten. Doesn’t get done.

Oh, and dump your cable TV service. Get the shows you actually enjoy from iTunes and Netflix and stop wasting time watching whatever’s “on”.

What’s your favorite thing to do when you’re not being an engineer?

I love to write. Not anything substantial, like novels or stories — just blog posts. Writing about a subject helps clarify, mature, and sometimes even change my opinion on a topic. Afterward, I feel accomplished and productive, and the responses I get are fulfilling, constructive, and often more numerous than I expect.

The Art of Not

I sign up for every single beta, trial, or preview that crosses my inbox as a virtual land grab for the “rands” username. Yes, I am very interested in whatever bleeding edge thingamahoo you’re up to, but the chances are this will be the only time I’m going to login into your service.

It is a function of my time, not your hard work. I’ve just searched for the word “invite” in the subject line of emails received since the beginning of the year and I’m looking at 20 new applications and services that showed up, and ironically, the one new service I’m using the most is the one for which I didn’t get an invite.

Yes, there are exactly zero emails from Instagram in my inbox, and that’s just the beginning of things they are successfully not doing.

Instagram Explained

Delivering the Instagram pitch is usually a study in disappointment.

Me: “You take pictures, tweak them with filters, and then share them with your friends.”

You: “Yeah, I have three of those.”

Same here. I grabbed Hipstamatic, took five shots, and didn’t use it again. I checked out Photoshop Express and ran screaming. I still regularly use TiltShift Generator, but that usage pales in comparison to how Instagram has become part of my day, along with 300,000 others and counting. And that’s with an impressive list of features Instagram doesn’t offer, including:

• A significant web presence: the interface is the iPhone application.
• Options for rotating or otherwise altering your photos, other than 11 filters.
• Complex social networking features.

Yet in a crowded market of low-end mobile photo editing tools, Instagram has become an overnight success. Why? They said no — a lot.

The List of Not

Granted, one of the documented reasons for Instagram’s spartan feature set is the size of the team. As noted in the Quora article, the team allegedly spent a year working on the foundation for what became Instagram. But it was in an eight-week period that Instagram was designed, developed, and deployed. They could have waited another eight weeks and added a bunch more features, but they didn’t. I think each omission is interesting.

The lack of a significant web presence. Yes, you can share the URL for an individual photo via the website, but virtually all other interactions with Instagram are via the iPhone application — the website is currently an afterthought. This type of product launch is a testimony to the buzz and strength of iPhone as a platform, but I think it speaks more to Instagram’s tight focus on the one key workflow: “Grab a photo in a moment, make it better, and share it — with everyone.”

Nothing in that workflow needs to involve a traditional computer. Everything you need to participate in this workflow is sitting in your back pocket. Yes, the social angle of Instagram would be improved by a vast swath of eyeballs from the web, and I’m certain that’s coming, but the opportunity for that feature to matter has been created by Instagram’s choice to first intensely focus on the one workflow.

Limited options for altering photos. Ok, I didn’t run screaming from Photoshop Express. It’s a well-thought-out application that provides a solid set of photo editing tools, but after brief experiments I’ve never used it again for the same reason I’ve never written much of anything on my iPhone.

The interface of the iPhone is moment-based. You’re in; you’re out. Yes, I’ve lost many hours getting angry with Angry Birds, but for most interactions I want to get in and get out as quickly as possible. When I fire up Photoshop Express, the application asks, “Are you ready to spend the next 5-10 minutes of your life adding effects and borders to that photo of your cat?” The answer is no.

Other than cropping a photo to a pleasing Polaroid-esque square, the only options for photo alteration are a minimal set of 11 filters. No color correction. No brightness. No contrast. Where Instagram chose to invest their time (and yours) was choosing a diverse set of filters that seem to improve just about any photo.

Too dark? Try the 1977 filter. Flat color? How about X-Pro II? Too much color, but lots of detail? Try Inkwell.

The Instagram folks could’ve lost their frakkin’ minds including any number of filters in their initial release, but they didn’t. They picked a sweet spot for filters that improve just about any photo without overwhelming you with choices.

Minimal social. Unlike many of the other mobile photo editing tools, Instagram does have a social component. There’s a backend service that uses a Twitter-like “we’re sharing everything unless you tell us otherwise” privacy model, but similar to other Instagram design choices, the social angle is simple.

Instagram heavily leverages the work of others with their social strategy. You comb your Facebook and Twitter friend lists as a starting point for a follower list, but more interesting is Instagram’s publishing feature set. It’s one area that’s feature rich. You can take your recently Instagramed photo and publish it to a bevy of services: Twitter, Facebook, Flickr, Tumblr, and Foursquare.

While this represents a lot of functionality, I still see Instagram’s social angle as a study in Not. In the battle for eyeballs, Instagram knows they’ll be more successful long term by not trying to be any of these established services, so they embrace them. Once again focusing on the last step of the workflow: “share it — with everyone.”

Regarding Product Market Fit

There’s an inflection point in product development dubbed “product market fit”. It’s a milestone when a given service or product has found its market and can now focus on building a business.

It’s comforting, the idea that there’s a moment where you can safely say, “All that hard work has successfully resulted in our fit in this market “. Unfortunately, it’s only an event you discover after it appears. It’s a milestone, not a blueprint.

So, how’d Instagram do it? How’d they swoop into a cluttered market and grab 300,000 sets of eyeballs in eight weeks? Were they lucky? No. Did the have the benefit of examining the work of those that went before them? You bet, but that’s not the biggest reason.

The Instagram team could have gotten lost in any number of distracting feature buckets. In fact, based on the Quora article, it looks like they did, but then they threw away that application and built one intensely focused solely on photos.

There’s lots more coming from Instagram. There are subtle clues throughout the application that it could be adapted to share any type of media. Whatever they choose to do, they now have the opportunity to choose because of what they chose not to do.

Your Cat. My Socks.

We need to talk about your cat because your cat is pissing me off.

Your cat is eating my socks. No. Really. Your cat has eaten four pairs of my socks.

Yes, I know cats can’t digest cloth. Your cat does not have super-feline sock-eating and digestion skills. Your cat nibbles the toes off my socks and then throws up these toe parts all over my closet floor as little gooey sockballs.

Your cat is pissing me off and we need to have a conversation about it.

The Topic of Conversation

In How to Run a Meeting, I describe a conversation as “verbal ping pong… you bat the little white verbal ball back and forth until someone wins”. This describes a simple conversation, but conversations are rarely simple. They have a variety of structures that are carefully negotiated and molded by the participants.

To understand the different type of structures, we need to define a base unit of conversation and the actions that potentially surround it. Let’s call this base unit of conversation a topic.

A topic is the headline you’d give to the current content and state of the conversation. Examples:

• The problem with our bug queue.
• I can’t stand Stan.
• You are bugging me in indescribable ways that I will now attempt to describe.

In my head, a topic looks like this:

The key parts of this model are:

1. Stop button. For any number of reasons, a conversation can stop or be interrupted. When this occurs, all conversation participants are effectively agreeing: “This topic is done and there will be no further discussion during this conversation”.
2. The agreed upon Topic of the conversation.
3. Progress Bar. This is a totally subjective measure that indicates how close a conversation is to being resolved. If the bar is moving, this topic is currently in play.
4. Pause button. A healthy conversation is rarely only focused on a single topic. Conversations meander from one topic to the next. When paused, a topic is no longer being discussed, but it remains open and unresolved in the minds of the participants.

This is a lot of preamble to describe an act we do automatically. If this model strikes you as overly complex, know this — you are going to spend half of your goddamned life suffering through the alignment of differing perspectives in any given conversation. It’s the single biggest waste of your time in dealing with other people and the better you understand, the less time you’ll waste. So, let’s circle back to…

Your Goddamned Cat

As we sit down to have our conversation regarding the sockballs littering my closet floor, I’m thinking about how I’m going to successfully convince you to keep your cat on a tighter leash. In fact, I don’t want the cat in the house at all, but you pay half the rent and we did agree when we arrived that the cat was cool. I need to figure out how to verbally amend that agreement, which means we’re going to need to negotiate. I’m going to have to concede something in order get the goddamned cat away from my delicious socks and out of the house.

In this case, I don’t know what my concession is — it’s something we need to discover via our conversation, which means there are a couple of potential topics:

1. Regarding your cat eating my socks.
2. The cat eviction negotiation.
3. Things I know that piss you off.

With these topics in mind, our conversation starts gently, in the living room. I explain, “I would like to discuss the matter of your cat eating my socks,” to which you respond, “I am sick and tired of you not cleaning the bathroom”.

Whoa. Wait. What?

In my head, the conversation looked like this:

But you just hit the pause button on our first topic and started another topic:

The second topic introduces a new element in the model — the segue. This handy line is the context that ties one topic to another, which, in the case of the sockball situation, is currently a confusing, “Wuh?”

The point: it takes at least two people to have a conversation, but the real work is in making sure you’re both having the same conversation.

I can help.

A Conversation Structure

In computer science, there’s a concept called data structures. The idea is that a data structure is a model used to organize data so that it can be used efficiently. One of the simplest structures is called a list and it looks like this:

In terms of a conversation, think of lists as the most basic and easy to follow type of conversation. Using the model I describe above, no topic can be paused or stopped until the topic is resolved. There are no segues, tangents, or sidebars.

You’re thinking conversations as simple and structured as these don’t exist, and you’re right. This type of meeting does occur, but it’s called a presentation — where the speaker is click-click-clicking through his topics on his merry way towards the undisputed end.

While this basic list of conversations doesn’t exist, there are people who want them to exist and will make this clear as part of the conversation. They sound like this:

• “Wait, wait, wait, we’re not done with topic #1. Can we talk about topic #1?”
• “Hold it, before we go there, what about the issue at hand?”
• “This new topic has absolutely nothing to do with what we’re talking about.”

The intricacies and implementation of various data structures are not the topic of this article. What’s relevant is understanding that there are different conversation models you might find yourself in and then figuring out how to adapt.

The Stack

A slightly more complex data structure, and one that is more representative of a real conversation, is the stack. This is where our Pause and Stop buttons come into play. Let’s go back to that goddamned sock-eating cat to understand. Our conversation started with the sock topic, but you immediately put a Pause on that first topic and fired up a new one. In my head that looks this:

This is a stack. The topics are literally stacked on top of each other because, in my head, we’re actually talking about both topics, and the successful conclusion of all topics is key to this entire conversation coming to a successful conclusion. The question is are we both prepared for this type of conversation?

My definition of an effective conversation is if, at any moment, you could ask any participant in the conversation to point at precisely which topic was being discussed and how that topic was progressing. Bonus points for walking through the stack and explaining how you got there.

When conversation participants lose the context of the conversation, when they lose track of where they are, they stop listening and stop participating. The conversation no longer has a chance of resolution because resolution requires their active involvement and all they’re doing is fake listening to your speech.

Conversation Tolerances

A stacked conversation, one with multiple topics tied together with segues, is where everyone involved needs to keep track not just of the complexities of the conversation, but of the tolerances of those participating. Again, this is not a meeting with a well-defined agenda and anointed leader; this is a conversation where everyone needs to keep their wits about them.

When a conversation gets complex, this is what I’m watching for:

How many open topics can we handle? Each segue moves us slightly further from the starting topic. Are you cool with that? Ok, how many topics can you keep in your head? There’s a point where everyone will lose track of where they are if we have too many open topics — what’s your threshold? Wait, now I’m lost, so I’m going to ask: “How’d we get here?”

What’s our segue tolerance? How deliberate do I need to be switching from one topic to the next? Do I need to explicitly say, “We are switching topics now,” or can you keep up? How much segue detail do I need to give? Can anyone hit Pause and pivot to a new topic? Will you? Ok, you just did, but I don’t understand your segue, so I’ll ask: “Please explain how this relates to that.”

What’s our closure tolerance? How much progress do you need to make before we switch topics? Will you get cranky if we don’t even try to resolve something? Is this topic more important to you than other open ones? Will you freak out if all is not resolved? Can the conversation totally mutate into something else? Is that a bad thing?

Understanding both your own conversation tolerances as well as the ones of those you converse with is essential to having a successful conversation, and the best way to know where they’re at is to look. Humans wear a bevy of visual cues that indicate their comfort with a conversation. Nods, sounds, and eye contact — these are potential signs of engagement. The rule is, if they look lost, you ask: “What did you just hear?” If you’re lost, you say: “I’m not following you.”

The Tree

Problem solving is the art of a finding a solution acceptable to everyone in the conversation. If everyone knew the solution to the problem, you wouldn’t be having the conversation in the first place. If there is no problem, then, well, you’re shooting the shit. Problem solving means getting conversationally creative, and being creative means letting yourself mentally wander — eschewing structure. This is why my favorite conversation structure is the Tree.

The Tree is the pinnacle of advanced conversations. Where a stacked conversation looks like this:

The tree appears chaotic:

The simple explanation of the Tree conversation is that it’s multiple conversations. In the image above, you’re looking at three seemingly disparate conversations, except they’re not. The reality and the definition of the Tree-based conversations are the inspired segues. Think of a conversation with your best friend. Would anyone listening to this conversation actually be able to follow it? Could they diagram it? Of course not.

Could you? Of course.

For qualified participants, the Tree is pure conversational joy. Topics vary wildly, being held together by only the thinnest of segues that are often unspoken, but there is a structure. And more importantly, there is mutual understanding and appreciation of this wonderfully chaotic verbal mess, because it’s in this mess where you have the most potential to resolve the topic.

Remember, this is a conversation; it’s not a story and it’s not a meeting. There is a topic to be resolved and no one is happy until that topic is resolved. If this was a trivial topic, if we could just tell your cat to stop eating my socks. Resolution might be easy, but it’s not. My spoken frustration about your sock-eating cat has triggered your response about my inept cleaning skills, which means now we’re going to do some heavy-duty roommate therapy.

The resolution might be tricky and it might involve verbally wandering to disparate topics, but you and I have known each other for years. We’re ok with a deep stack of topics that eventually transform into a forest of conversations. We know that part of big discovery is verbally wandering into strange mental places.

How to Be a Douche

Douche is trending.

I’m going to start by saying this is a dangerous article to write because an article that attempts to define the characteristics of douchery is, well, kind’a douchey. However, usage of the word douche has been on the rise in current culture and I believe I know why, so I’m going to risk it.

In the preface to Being Geek, I briefly explained the definitions of geek, nerd, and dork. While my research found no meaningful distinction between nerd and geek, the term dork was interesting — while being a geek about a topic (say a music geek) means that you are self-declaring that you deeply appreciate a thing, dork is used by geeks to position their geekery above another geek’s field. For example, I’m a computer geek, but those movie geeks are dorks.

See?

It’d be easy to simply map douche to dork and say that douchery was in the eye of the beholder, but I think there is something bigger going on with douche. The label of douche, while slightly hilarious, is also slightly serious.

The Douche Spectrum

To begin to understand the deviousness of the term douche, we need to explore its basic usage. There are three douche use cases:

Self-declaring as a douche — “I can’t figure out how to write this bio without sounding like a douche.” A mostly harmless usage.

Labeling as douche in person — “Your unearned high self-esteem… is kind’a douchey.” Again, a face-to-face douche label is, in my opinion, just good constructive criticism.

Lastly, labeling as douche in absentia — “I’m tired of his transparent self-serving bullshit. He’s a douche”. In an Internet full of individuals screaming for attention, this label is the kiss of death. Here’s why:

The Sell

If you’re taking the time to create and post content on the Internet, you are in the sales business. You’re interested in someone buying the content; otherwise you’d be quietly taping that content to the wall of your office.

Rands, I want no money. There is nothing to buy.

Doesn’t matter. Just because you’re not charging for it, doesn’t mean you’re not selling it. Yes, there’s a wide spectrum to selling varying from “I’m selling you on this idea” to “Please buy this poster regarding how to pet a cat”, but the act of sharing something with the Planet Earth has a very different motivation than sharing with yourself, and it’s within this act that the dangerous label of douche is hiding.

A Douche Criteria

The label of douche is the end result of a confluence of terribly subjective and contextual cues. As I’m reading your writing or watching your presentation, I mentally measure the following:

Are you for sale? Is it clear that your opinion is being motivated purely by money? Can I literally see the monetary strings dragging you hither and fro? Can I hear your thoughts above what is clearly your business plan? Am I hearing what you’re selling before what you think? Are you never missing an opportunity to self-promote?

Is fame your goal or a consequence? Is your content deliberately inflammatory because you like to see shit burn? Are you enthusiastic with purpose or just annoyingly enthusiastic? Are you just trying to get attention? Wait, are you telling me you’re famous? Really?

Are you human? Are you letting a bit of yourself into your ideas? Can I see you thinking? Do you have moments of humility? Empathy? Where do you end and your ideas begin? Are you just a mouthpiece? Can I discern your motivation?

Is there substance to your style? Did you earn your arrogance? Are you adding something substantive to the planet or are you just noisy? Are you pitching refinement as a mask for aggressively bad taste? Do I have a sense of your experience? Are you beating me over the head with it?

Are you aware that anyone else is here? Are you giving me room to think? Do you speak without understanding consequence? Are you aware of the world around you? Are you transparently self-serving?

Are you a douche?

The Douche Threshold

What matters to you is different than what matters to me. I have a douche hot button — blatant self promotion — but you couldn’t care less. Still, when you label someone a douche, I giggle bit and then I wonder, “What do you actually mean?”

In this age of the empowered individual voice, we are flooded with opinions in blogs, tweets, and likes. As a means of managing this flood, we need a mental model to partition these unincorporated individuals — we need a new vocabulary regarding who is worth listening to and not — I believe that is why the term douche is trending.

The extreme subjectivity of the Douche Criteria can get you in a lot of trouble. If I had to boil all of the criteria down, I’d say the lazy version of the Douche Criteria is, “Do I like you?” Human beings are most comfortable when surrounded with those who look and sound alike — who share the same values. Outsiders are viewed first by their differences rather than their potential. Yeah, it sucks.

My optimistic hope is the Internet hides the individual differences that don’t matter while providing a stage for ideas. This is why the term of douche is not a goofy label that says, “You’re different”, it’s a personal and essential judgement of authenticity.

(This post would not exist without the fine suggestions of the very-non-douchey folks who follow me on Twitter.)

An Unexpected Connection

Blue whales.

I couldn’t fucking stop researching blue whales. I was 12 and my teacher had just explained to the class that blue whales are the largest mammals on planet Earth.

In hindsight, this reaction was my first confirmed sighting of what in The Nerd Handbook I call the “annoying efficient relevancy engine”. Something in the phase “largest mammal on earth” started the relevancy engine and once it starts, it’s not going to stop until the relevancy is understood.

Two Buckets

The relevancy engine is the nerd’s ability to instantly and with little conscious effort parse all incoming information into one of two buckets: relevant or irrelevant. It’s a defensive information management strategy built as a reaction to the nerd’s innate passion for information — for understanding. See, a nerd can and will find out everything about anything, and left to their own devices, they’ll do this… endlessly.

Items placed in the irrelevant bucket are aggressively ignored, whereas the items in the relevant bucket are flagged as compelling and are, if possible, immediately investigated.

The reason for this often-unavoidable research compulsion varies by topic. There is something tucked inside of the idea — a puzzle, a game, a system to be discerned — that triggers the nerd’s pleasure centers, and, once triggered, the only course of action is understanding. This is why, when you’ve piqued my interest, I keep asking questions, incessantly, while staring you in the face… never blinking.

The Value of Relevance

The real value comes when we’ve vetted the relevant. The act of obsessively researching yields even more relevant data that allows the nerd to fully index the idea. A mental notepad is created that reads “Blue Whales” and on this notepad is written the three most relevant and interesting facts that make blue whales intriguing. This card is then carefully filed away.

This collection of esoteric indexed data is why a nerd’s knowledge feels five miles wide and three inches deep and why we’re randomly great at games like Trivial Pursuit. See, four years ago, someone mentioned the largest organism on the planet was a Quaking Aspen tree. We heard that one relevant fact and then spent two hours investigating the various methods by which a largest organism might be measured, we read about the largest known fully connected Quaking Aspen grove in Utah, and ended up reading about the world’s largest single stem tree, a Giant Sequoia named General Sherman.

It sounds like a lot of work until you understand the payout.

To Wit

Nerds are fucking funny. It’s another point from The Nerd Handbook that I suggest is related to the relevancy engine, but I never explain. Let’s try now.

The processing of relevancy has three steps and it’s the third where the magic happens:

1. Collect the Relevant
2. Research and Index if necessary
3. Connect the Relevant in Efficient and Entertaining Ways

So, how is The Funny created in this flow? It’s a big question: what is funny? I’d say there are two big classifications of funny. There are jokes and there’s wit. Jokes are memorized comedy retold with moxy. Wit is original comedy created in real-time and delivered with precise timing. Nerds are fucking witty because they connect the relevant to the present quickly and in clever ways.

Have you ever sat in a meeting full of engineers? What’s the game? The game is “Who can say the funniest and/or snarkiest thing and get the biggest laugh?” and to play you need to kick the relevancy engine into high gear. You need to hear everything being said, parse it, compare it to everything you know, and then find the most relevant connection possible. In nanoseconds.

Laughter is often the by-product of these observations, but an equal amount can be the hard silence found amongst the discovery of an uncomfortable truth. It’s at that moment you realize the primary goal is not laughter, but the art of the impressive connection.

Connecting the Relevant

The art of the connection is the end result of a nerd’s highly obsessive due diligence performed on anything that falls into the relevant bucket.

Laughter is sometimes the end result of connections — the recognition of the Clever between two dissimilar items or the absurd lack of any connection at all — but the result in the nerd’s brain is far more satisfying. A successful connection brings efficient order to the two heretofore-unrelated objects, and you know what that means: we’ve discovered structure. This is related to that. I know more than I did a moment ago.

Discovery of structure in a chaotic world means less chaos, and while we’re happy to make you laugh, the idea of a more orderly, structured, and knowable world is what drives us and keeps us warm in bed at night.

Being Geek: The Trailer

Being Geek by lonelysandwich. Available on O’Reilly and Amazon

Chill

In my teens, I got migraines. Maybe it was growing pains, but all I knew is that randomly and without warning, I’d get a splitting, seeing spots, curled up in a dark room headache. Painkillers didn’t help. Meditation merely distracted, diet was out of the question — hello, teenager — and I got regular exercise as part of the cross-country team.

After a particularly bad July, the girlfriend at the time suggested, “My Mom does biofeedback, you should give it a whirl,” to which I responded, “Does she sell mood rings, too? How about pet rocks? Hulu hoops?”

She ignored me. “It’s not like that. She can show how your body reacts to different stimuli.”

“Do I have to sing Kumbaya?”

“No.”

I Think I’m Breathing

The process of being wired up for biofeedback is intimidating. A variety of sensors measure brainwaves, heart function, breathing, muscle activity, and skin temperature. Once wired, you can literally see the collection of systems that is your body working in concert.

It gets interesting when you start ignoring the feedback. “Rands, we’re going to try different relaxation techniques and see what works. How do you relax?”

TV? She turned the TV on for ten minutes. “Yeah, that doesn’t relax you. Your brain is working.”

Closing my eyes and breathing deeply? Five minutes later, “Again, it looks like you’re thinking too much about not thinking. You’re not relaxing.”

What about reading? She pulled a book off her shelf and I started reading. Within a few minutes, all of the feedback pointed out that my body was diving into a deep relaxation.

“Rands, reading chills you out.”

Weeks later, when the next migraine began to creep up the back of my head, I grabbed Ender’s Game and read. In 30 minutes, the tiny tendrils of pain began to vanish. In an hour, the migraine was gone. Reading was never a cure-all for every migraine, but reading gave me shot at by-passing a crippling day of pain.

Chilling Out is Essential

If my prior report that a third of high school graduates never read another book didn’t freak you out, here’s a different pitch on why we want people to pick up a book: reading chills you out.

I’ve no idea whether my biochemistry is indicative of the rest of the planet or not, but I know if the world is freaking me out, reading calms me down. The act of pulling words off a page and constructing a thought forces me to clear my head, discard stress, and find my mental footing. In a world where whomever is screaming the loudest sound bite is considered to be providing information, I think the act of chilling out is essential.

And you can help with the chill. I offer you the second Rands in Repose benefit t-shirt.

This year’s logo is designed by Victoria Wang, who designed the shirts for the now scuttled C4 conference. The shirt itself is a product of the Continental Clothing Company and is constructed of insanely soft 70% bamboo. If you haven’t given a bamboo shirt a try, you haven’t really chilled out. Once again, the folks at buyolympia.com have made finding, printing, and selling shirts a simple process.

As with the previous shirt, 100% of the proceeds from each shirt go to First Book, a nonprofit organization with the mission to give children from low-income families not just the opportunity to read and to own their first new books, but a chance to learn how to chill.

The Shop I Want

Until recently, I’d never been to IKEA, mostly because of fear. I knew there would be things I wanted, but the IKEA reputation kept me away.

What I heard:

• It’s huge
• It’s a maze
• You can’t get out in less than three hours
• It’s full of people.

While I guess I need flat-pack design furniture at affordable prices, this is not the shop I want.

You know, Everything

Back when eBay was novel, I played a game with the family before a Thanksgiving dinner. As a means of introducing the idea of eBay to them, I asked each member to describe a thing they wanted that they believed would be hard to find. The sister wanted an antique printer’s box, the Mom was looking for a vintage lens, and the Dad, an electrical engineer, requested a now forgotten device that I will dub a hibblygizmo.

“Ok, so these are things you want that you believe would be hard to find, right?”

Collectively, “Yes”.

“And how would you go about finding them?”

Again, collectively, “No clue”.

I spent the next ten minutes confirming what I already knew. All of these items, however esoteric and including the hibblygizmo, were readily available as active auctions on eBay. I printed out each of the auctions and handed the paper to each member of my family, saying, “Happy Thanksgiving. You now live in a world where a shop exists that has everything.”

Unfortunately, this is also not the shop I want.

Regarding Abundance

The shop I want is owned by a person I know and respect. Inside of this shop are two button-up shirts, a pair of jeans, three pens, a desk, and a small white marble polar bear. Each of these items is picked out specifically for me, and more importantly, they are items that, given my own devices, I would never choose or possibly even discover for myself.

As I walk in this shop, the proprietor sees me and grins. “Rands, I have the perfect desk for you.”

“I don’t need a desk.”

“You need this desk. It’s vintage Stow Davis. It’s walnut with solid brass and wood handles. It’s the perfect size for your Cave.”

“I don’t need a desk.”

“Stow Davis. Founded in 1879. Did you know Frank Lloyd Wright commissioned them to produce furniture in the ’30s?”

This mythical person is not going to stop until I’ve purchased this desk because this person knows me and knows that this desk is perfect for me.

I Said, Everything

We’re in a world where you can find anything you want, which is great, except when you realize there’s a lot of everything. Google was created and thrives attempting to solve the everything problem for us. Google has made it wonderfully simple to find a thing, but just because you find a thing doesn’t mean you care about it. As you stare at a PageRanked list of stuff, you have a choice:

You can sit back and be force-fed the decisions and opinions of others. Many of the people who are making these decisions are not evil. They are well-paid, well-intentioned, bright people whose publicly traded companies have built astoundingly profitable businesses building and marketing things they want you to think you need.

These people think they know you because they’ve done the math. They believe you fall into the Stow Davis-inclined IKEA-fearing writer slash surfer demographic, and that’s a strong demographic. Knowing this demographic, they can answer the question: “How can we move 72,000 more of those things on this demographic? How are we going to give the impression the mundane is unique?”

Or…

You can have an opinion. It sounds like work, but it’s really not. An opinion is not the definitive view or judgement regarding a thing; it’s you staring at that desk and saying, “You know, I like the look and the feel of those brass handles. I also like the drawers that squeak just a bit when you open them. It speaks to the character of the whole desk.”

It’s not that I want a Stow Davis desk, it’s that I want to find that desk. I want to go to seven different antique shops and spend a weekend developing an opinion about the state of antique desks. I want to find someone who knows the entire history of Stow Davis desks and won’t fucking shut up about them.

Half the fun of having an opinion is the quest to find one, but the everything problem remains. You don’t have the time to have an opinion about everything, but someone has the time.

My Shaving Cream is Crap

It is. It’s waxy pumpkin-smelling crap and when I ran out, I thought, “Good riddance”. I am now faced with two problems: first, I need new shaving cream, and second, my instinct is to spend the entire goddamned weekend researching shaving cream in a compulsive quest for complete understanding of all there is to know about the shaving cream world.

While I want to have an opinion, I do not have time for this exquisite shaving cream expedition, but someone has already completed this quest and has an opinion I can trust. I just need to find them, so I do:

An amazing thing happens when you ask for help, people respond. In their response, not only do you get their opinion, you also get brief glimpse into how they tick, and whether or not that ticking is aligned with yours. When I asked on Twitter for shaving cream help, not only did I learn more than I ever thought possible about wet shaving, shaving cream, straight razors, and a bevy of other shaving topics, I also found five more people to follow because in 140 simple characters, they told a story that reminded me that the best way to search the Internet is with someone you trust.

The Shop I Want is Full of Stories

The shop I want does not exist because this impossible shop is full of people spread across the planet. There’s Tasha who can explain anything about grammar. Scott can tell you anything about the Smashing Pumpkins and he also makes a Mac’n’Cheese for which I will fly across the United States to reverse engineer his recipe. Boris is in this shop and he’ll talk about scuba diving until I ask him to stop. I’ve collected each of these people and placed them in this impossible shop because, at some point in the past, we discover a common trait or idea that tied us together - we discovered that together we could explain the world to each other.

I don’t need flat furniture nor do I need a desk. I have enough pens and journals. My closet of full of shirts and while I still wonder what a hibblygizmo is, I’m certain I don’t need one. What I need is shop full of people with opinions — because it’s not what I know that I’m worried about, it’s what I don’t know that’s really interesting.

The shop I want is full of people who are dedicated to their opinion. Who are happier understanding a thing rather than wanting it. These people will happily tell the story of happened upon this opinion and I want to hear it because the opinion of someone I trust is just as valuable as my own.

Bits, Features, and Truth

There’s a meeting going on right now. It’s a cross-functional meeting, which means that not only are multiple departments in the organization represented, but multiple expertise types, attitudes, and agendas as well. The cross-functional nature of this meeting means a program manager is present and they are likely serving in their role as translator.

See, good program managers speak all the regional dialects of the company, so when engineering says, “It’s done,” they jump right in and translate: “Done pending function testing, production testing, and final documentation review,” so that product management doesn’t tell sales, “It’s done,” and they start selling something which actually isn’t done.

In this well-attended multi-lingual meeting, a decision is on the table and it’s a decision that’s happening in every single software company right this second. It’s not really a decision, it’s a negotiation, but it’s on the table and people are tense because this decision is under heavy scrutiny:

Product management: “What’s it going to take get this feature done?”

Program management: “What he’s asking is…”

Engineering: “Quiet, I know what he’s asking. The answer is, do you want to sacrifice TIME, QUALITY, or FEATURES?”

Program management: “What HE’s…”

Product management: “Yeah, I’ve heard this before and I still want it all.”

More talking. More translating. Action items are assigned, which gives everyone the illusion that progress was made. And we all return to our respective regional offices and wait until we have the same meeting again, where we attempt to communicate intelligently with each other. But all we really do is schedule meetings… when what we need to do is figure out who makes decisions.

That Damned Triangle

Time. Quality. Features. It’s usually described as a triangle, which somehow represents the state of your product or your feature. I believe the idea is that in a perfect and unattainable world, this triangle is perfect, equilateral, and seemingly at rest. There is balance among the time you have to release, the quality you are seeking to attain, and the features you want to ship.

In reality, this triangle is never at rest. It’s constantly shifting and, well, I don’t think it’s actually a triangle. It’s just a mental model that gives you just enough ammunition to lie. The conversation goes like this:

Product management: “We need this feature to be competitive.”

Engineering: “Ok. We need four extra weeks to do that feature since it’s new and you’re asking late.”

Product management: “The date can’t shift, we made commitments.”

Engineering: “So did we. Listen, something has to give. You’re adding more work or features, which means we need more time, or, if you want, less quality. Make a choice.”

These black and white arguments don’t hold water. The idea that there are three simple levers that define a feature or a product is passive-aggressive professional absurdity. There are myriad levers the team can adjust, but to understand them you need to understand the people who are actually building the software.

Bits, Features, and Truth

Let’s start with an exercise. I want you to think about the project that you’re working on, or, if your project is ginormous, I want you to think of the feature that you’re developing. Relative to this product or feature, I want you to walk up to your nearest whiteboard and draw three large circles:

Now, a name belongs inside each of these circles and it’s the name of a specific role on your team. The traditional titles for these roles are engineering manager, product manager, and program manager, but I don’t want you get to get hung up on titles. I want to you to think about the person who is best qualified to make a decision regarding the bits, the features, and the truth.

Bits: Who is the engineer who has the most influence on the bits? There are likely influencers, but who is the engineer that everyone goes to when they have a question. Your manager’s name is a good knee jerk name to put up here, but just because they have “manager” in their title doesn’t mean they know what’s going on as well as where to go. I want the name of the person who not only gets the call in the middle of the night where there is a bit-related emergency, but also the person who makes the large bit-related decisions. I want to know the name of the person who, when they say no, the debate stops. Got it? Ok, next.

Features: Who is the person who defines the content for the product or feature? This is the name of the person who is constantly asking for more without regard for cost. This is the person who can eloquently and calmly explain the need for this feature with an argument stronger than, “Wouldn’t it be cool if…?

Truth: This might be the hardest to define because it’s a role that could live anywhere in the building. While it took years to form this opinion, I believe the person who is responsible for the process is the one most likely to be the keeper of the truth.

There’s a constant ebb and flow of information in any group of people. Important decisions are made in the morning that can take hours or days to move to the other side of the building. Information is tucked away for nefarious purposes. Information is laundered, adapted, and misinterpreted.

The truth is the aggregate best set of information that exists in the building, and the person who consistently has it is the keeper of the truth. You know this person; it’s the person you go to when you’re wondering, “What the hell is going on here?” This is the person who knows the politics and the players, they know the real reason the product is late, and this is why this is usually the job of the program manager.

The complaint I hear most about program management is the same complaint I hear about managers: What do they do all day? What do they actually own? Practically, the most important part of the product they own is the schedule, but their larger contribution is information management.

Yeah, I know you start-up folk believe you’re doing just great without a semblance of program or process management. You believe that these types of folks are going to slow you down with their agendas and to-do lists. Here’s the deal: just because no one has the title in your garage doesn’t mean the role doesn’t exist. In any group larger than one, someone has taken the role of keeper of the truth and their key skill is information wrangler. They constantly gather the information from the group, synthesize it, translate it, and, sometimes forcibly, present this information to the folks who are busily lying to themselves.

Me: “We have six weeks to shipping, we’re good.”

Keeper: “Feature complete was two weeks ago and we’re still writing code.”

Me: “But the team is fired up, working weekends, and…”

Keeper: “Steve and Ryan are on vacation for two weeks starting tomorrow.”

Me: “Oh.”

A good program manager cares about the program and the product, but they also have a calm professional ambivalence. They have to — they’re always uncovering and then surviving the worst-case scenarios. These discoveries often give them the most complete picture of how the product is doing. Their ability to survive them has made them unflappable - they don’t freak out because they’ve lived through it and know there’s always a way out… somehow. All of this experience is why they usually end up owning the schedule. I’ll explain why when we get to analysis.

So, who is this calm, truth-oriented, well-informed person on your team? Who is the person who doesn’t lose it? Who is the person you go to to understand the intent of the other parts of the organization? They very well might not have the title of program manager, but they are there.

Circle of Comfort

Before I analyze your circles, I need you to do one more pass where you ask yourself two questions.

Great, you’ve got a name in each circle. Maybe the same name is in two circles. We’ll talk more about that in a moment. My first question is: for each name, what’s the person’s circle of comfort? It’s fine that you put Ryan in both Bits and Features, but where does his heart lie? What is his professional background? Which circle is he going to instinctively optimize for? For each circle, if you think the occupant’s natural circle is different, write that name underneath their circle.

My second question is: have you picked leaders? Look at the Bits circle. The name you put in there is the brightest engineer in the building, and any time anyone needs someone to explain the architecture, he’s the guy paraded across the building, but is he the leader? Does he make decisions about the direction of the product? He has incredibly strong and informed opinions about where it’s going, but when it comes down to the commit, is he the guy? No? Ok, who is?

Leaders have deep experience in their circle. It’s not chutzpah, it’s not spin; it’s the knowledge and analytical skills developed from doing the job. It’s because you can walk up to them, present a hard problem, and have an immediate, informed, and comforting answer. That’s the name that belongs in the circle.

Leaders make decisions. Sometimes it appears they’re doing it with little data. Some decisions are great, others are crap, but for the purpose of this circle exercise, you need to identify the three leaders relative to the Bits, the Features, and the Truth.

Circle Analysis

Ok, what’ve we got? Let’s walk through different circle scenarios:

- Something is empty. We don’t have program management, nor do we have any product managers. Again, don’t get hung up on titles. Just because your company hasn’t hired these folks doesn’t mean the work isn’t happening. Someone is picking features. Someone is designing the schedule. In fact, if you’re really small, there’s a chance the same name fills all three circles. Let’s talk about that.

- Same Name. All three circles. Edgar is the man. He’s our one-stop decision machine. It’s awesome. While I appreciate your velocity as well as your enthusiasm, I have concerns.

I believe an effective team eventually needs each of these roles clearly defined and owned by three separate people. Rands, where’s QA? What about design? HELLO SALES. These are essential parts of the business. WHERE ARE THOSE CIRCLES? This model is not about describing an effective business; it describes an effective team. Sales, design, QA, marketing, customer support — the list goes on. You need some version of these in order to have a business, and yes, they feed essential data into the product, but my assumption is that one of the reasons you wrote Mitchell’s name in the Feature circle is that he has a solid relationship with the design team; he knows that an essential part of his features is the design.

Three leaders. One who makes decisions regarding the bits, another who is responsible for the features, and another who cares about the truth. The theory is, these leaders are sitting in these circles because they have the ability to make good decisions relative to their expertise and the reality is these folks do not get along.

Program management believes engineering will never ship, product management believes the product would be nothing without them, and engineering thinks everyone else is useless because they don’t know how to code. It sounds pretty hostile, except when it comes to these three leaders. See, in addition to decision-making authority, these folks have healthy tension with their circle peers.

I divide healthy tension into two equal and opposite beliefs:

- First, there’s the reality-affirming belief that most everyone in the building shares. It’s the belief that my job is the most important job in the building and in my absence it’ll just fall apart. It’s a quiet belief that we tell no one, but it’s a silent strengthening belief that gives folks the confidence to make a decision. I’m an expert, I’m brilliant, and I’m right.

- Second, and specific to our circle denizens, there’s the grudging respect for the other circles and the trust of their expertise. This is a tenuous arrangement given the first belief, but part of leadership within the circle is the ability to step back from a massive decision and say, “He knows better than I”.

The idea is that the ability, skills, and experience that define each of these leaders are fundamentally different. An engineer who has seven years of coding experience has a vastly different perspective regarding features and products than a product manager who has transformed an MBA into a product management gig. You can fake it — an engineering leader can have a passionate opinion about a feature or a product — but there is a skill to defining, explaining, and justifying a feature that years of development won’t give you.

If you’re staring at your three circles and the name is the same in all three, I have two questions:

Are they all that? Can they consistently make correct bit-related decisions along with feature decisions while realistically balancing the truth? Really? If it’s the two of you in that garage, I get it, but if it’s 100 of you and one person is responsible for all three circles, I bet they are optimizing for their circle of comfort and that means two other circles aren’t being represented.

Who do they argue with? Without the healthy tension between Features and Bits, there’s no debating feature roadmaps and technical realities. A diversity of opinion takes any idea and hopefully shapes it into something unpredictably better. We can see good examples of this by looking at two other circle configurations.

- Bits and Features are the same. So Ryan, an engineer by training, is making both engineering and feature decisions. Great. That gets rid a lot of those pesky feature prioritization meetings, right? What other meetings aren’t happening? Where else is the feature set of your product not being debated because Ryan is making unilateral decisions as owner of the bits and the features?

Again, I’m being an alarmist and I’m exaggerating, but I believe you cannot effectively (and don’t want to) remove yourself from what you do to make a well-informed decision outside of your circle. Think of it like this: is Ryan the customer or does he have direct access to the customer? If the features are for engineers, there’s a solid argument that he could make decisions for both the bits and the features, but if the product or features aren’t targeted for engineers, why do we believe Ryan can make informed decisions about them?

I’m not saying that anyone outside of the feature circle can’t have an opinion about the product. You want a culture that encourages everyone to care deeply about the product you build, but if you’re developing software for regular human beings then you need a regular human being to speak to their needs.

Let’s look another variant.

- Truth is the Same as Features. Tony the business guy owns both the features and the schedule. This is a pretty common configuration because the belief is that those who make feature decisions for the user should also make scheduling decisions. We need feature X in May. What’s the hitch?

Well, you’ve got the truth bundled with the features and I’m uncomfortable with that because the truth needs to be neutral. The truth needs to be unbiased, and with Tony’s name in both circles, you’ve got the guy who is calling the shots for the features almost making the schedule decisions. He might have solid healthy tension with your Bits circle, but how is Bits going to argue with the guy who owns the levers for both content and time?

The healthy tension created by having three distinct leaders creates diverse debate about your product. Yes, this is the same debate I talked about at the beginning of this article, but the difference is when you have three leaders equally representing a well-defined viewpoint along with a sense of ownership, it’s a balanced debate where the needs of the technology are weighed against the desires of the customer and the realities of the schedule. When one leader is representing two circles, their two votes are pushing decisions in their favor.

Let the Negotiation Begin, It’s About the Debate

This is just another model. I’ve replaced the Time/Quality/Features triangle with circles. There are just as many ways to screw up and misrepresent this model with politics, inexperienced people, and poorly defined features. The difference here is I believe this model not only realistically describes the forces that pull your product in different directions, it also gives those forces a proper name.

Let’s go back to the endless debate where the Bits, Features, and Truth are equally represented:

Features: “I want feature X and I want it on the same schedule.”

Truth: “We need more time and since I know all the moving parts, I know that we’re ahead of schedule of one feature. I think we’ve got two weeks of wiggle room.”

Bits: “Two weeks isn’t enough. Can we cut this one feature that we haven’t started and no one cares about in half?”

Features: “I can live with that.”

Truth: “Sold.”

Software is built by people. The best Gantt chart only tells you half the truth about the schedule; the most complete marketing requirements document can never describe why a feature is compelling; and the most detailed technical specification will never tell you what makes for beautiful code. These are only tools and they tell little about the people who are building the software.

These people have names and they’ve earned them by not only making consistent great decisions for their area of experience, but also knowing when to ask someone else for advice.

B.A.B.

My management team was bickering. Two managers in particular: Leo and Vincent. Both of their projects were fine. Both of their teams were producing, but in any meeting where they were both representing their teams, they just started pushing each other’s buttons. Every meeting on some trivial topic:

Leo: “Vincent, are you on track to ship the tool on Wednesday?”

Vincent: “We’re on schedule.”

Leo: “For Wednesday?”

Vincent: “We’ll hit our schedule.”

Leo: “Wednesday?”

Endless passive aggressive verbal warfare. Two type A personalities who absolutely hated to be told what to do. My 1:1s with each of them were productive meetings and when I brought up the last Leo’n’Vincent battle of the wills, they immediately started pointing at their counterpart: “I really don’t know what his problem is.”

I do. They didn’t trust each other.

On the Topic of Trust

There’s a question out there regarding how close you want to get with your co-workers in your job. There’s a camp out there that employs a policy of “professional distance”. This camp believes it is appropriate to keep those they work with at arm’s length.

The managerial reason here is more concrete than the individual reasoning. Managers are representatives or officers of the company and, as such, may be asked to randomly enforce the will of the business. Who gets laid off? Why doesn’t this person get a raise? How much more does this person get? Profession distance or not, these responsibilities will always give managers an air of otherness.

Here’s my question: do you or do you not want to be the person someone trusts when they need help? Manager or not, do you see the act of someone trusting you as fitting with who you are?

Yes, there’s a line that needs to be drawn between you and your co-workers, but artificially distancing yourself from the people you spend all day every day with seems like a good way to put artificial barriers between yourself the people you need to get your job done.

Is that who you are or who you want to work for?

The topic of trust is where I draw a line in both my personal and management philosophy. My belief is that a team built on trust and respect is vastly more productive and efficient than the one where managers are distant supervisors and co-workers are 9-to-5 people you occasionally see in meetings. You’re not striving to be everyone’s pal; that’s not the goal. The goal is a set of relationships where there is a mutual belief in each other’s reliability, truth, ability, and strengths.

It’s awesome.

And it’s something you can build with a card game.

BAB

It’s pronounced how you think. Rhymes with crab. It’s an acronym for a game which, with practice, will knit your team together in unexpected ways. It’s Back Alley Bridge. Here are the rules, but before I explain why this game is a great team building exercise, you need to understand a few of the rules.

BAB isn’t bridge. The game does have a few important similarities. First, it’s a game for four players, involving two teams — the folks facing each other are on the same team and share their score. Second, it’s a trick-based game where the goal is for each team to get as many tricks as possible. A trick is won when each player turns up a card and the highest wins, unless someone plays a trump suit, which, in the case of BAB, is always spades.

Bidding. Also like bridge, BAB has bidding, meaning each team bids how many tricks they think they’re going to get after the cards have been dealt. Scoring is optimized to reward teams who get the number of tricks they bid and heavily punishes those who don’t get their bid. Bidding is a blind team effort — you have no idea what your teammate has in their hand other than what you can infer from their bid.

Decreasing hand count. Unlike bridge, the number of cards each player gets decreases with each hand. Each player gets 13 cards in the first hand, 12 in the second, and so on. Play continues down to a single card and then heads back up to 13. A work-friendly modification I’ve made is to only play every other hand (13-11-9, etc.) This number of hands fits nicely into a lunch hour.

Hail Mary. There are two special bids: Board and Boston. A bid of Board indicates the team is going to take every single trick. A board of Boston indicates the team intends to take the first six. Achieving a Board or Boston can be an impressive feat and is rewarded handsomely from a scoring perspective. Failure results in a scoring beat-down. Both of these special bids allow for wild variances in the score, which can be handy for teams who are falling behind.

Scoring, game play, and other information are in the complete rules. Now, let me explain why I picked this game as a recurring weekly lunch meeting.

In BAB, you talk shit. I’ve landed BAB in three different teams now and in each case, the amount of trash talking that showed up once players became comfortable with the game was impressive. This is a function of my personality, but it’s also a byproduct of any healthy competition amongst bright people. It’s also a sign of a healthy team. I’ll explain.

Trash talking is improvisational critical thinking — it’s the art of building comedy in the moment with only the immediate materials provided. As I’m looking for candidates for my next BAB game, I’m looking for two things: who will be able to talk trash and who needs to receive it?

The art in talking trash is the careful exploration of the edges of truth. When someone effectively lays it down, they say something honest and slightly uncomfortable. The ever-present risk with trash talking is when that line is crossed. It’s that one thing that is said that goes too far and offends, but it’s the presence of that line which makes talking trash so much fun.

It’s these honest and dangerous observations that form the basis of trust. When a co-worker makes a big observation about you and shares it with the other players, you take note - someone is watching. It sounds problematic, but remember, we’re just sitting here playing cards. It’s safe.

In a new BAB game, it takes players time to get used to the trash talking, especially in a situation like Leo and Vincent’s. Adversarial co-workers playing on the same team need to learn to ditch the business for the game. They need to understand there is a relationship outside of the daily work and there’s nothing like a comedic verbal beat-down to remind them to lighten up.

In BAB, you learn things unintentionally. Once you’ve got an established game with regular players who all know the rules, you’ll learn two things: people get better at trash talking with practice, and information travels in unpredictable ways in groups of people.

It goes like this:

• Player #1: “I bid 3.”
• Player #2: “I bid 1.”
• Player #3: “Pass.”
• Player #4: “Kevin’s quitting. I’m sure of it.”
• Player #1: “Yeah, I know.”
• Player #2: “Sucks to be you.”

Out of nowhere, in the middle of the game, you’re suddenly assessing the departure of a co-worker. I see this as a sign of a thriving, healthy BAB game because the team has begun to trust each other more. In the safety of the game, they’re letting the worries of the moment spill onto the table for all to see, which is impressive, since everyone knows that anything on the table at BAB is fair game for talking shit.

In BAB, you’re having work experiences without the work. Relationships need time to bake. Trust doesn’t magically appear; it’s cautiously built over time via shared experience. The majority of these experiences are created during the regular work day and I’m certain there are a great many healthy professional relationships that are defined and maintained in this manner, but I want my teams closer. I’m not suggesting group hugs and voices united singing Kumbaya. I’m looking for each team member to have the opportunity to understand each other slightly more than what they see when they’re at work.

The more you understand how your co-workers tick, the better you’re able to work with them. You’ll stop seeing them as the role, the title, or the keeper of a particular political agenda. They are just… Phillip. And you know what I know about Phillip? He’s the manager who used to wait too long to speak in a meeting. He had plenty to say that mattered, but he used to be too shy to say it.

Two months of trash talking over BAB showed me his reservations, so I learned to pull Phillip into the meeting conversations as quickly as possible. After a few pulls, he started to do it himself. After a few weeks, you couldn’t get him to shut up.

The Second Staff Meeting

The inspiration for the game came from a regularly scheduled bridge game at Netscape, and there’s nothing special about BAB that makes it the perfect lunchtime game. I chose BAB because a team-based game that fits nicely in a lunch hour.

You bet I maneuvered Leo and Vincent onto the same team for weeks on end. There was no magical moment during one game where they suddenly understood each other. Leo and Vincent continued to bicker in meetings, but over time the tone changed from the passive aggressive to the playful talking of trash. They turned competition into something healthy and fun.

In the safe competition that is BAB, you learn not only how to work better together by understanding that winning doesn’t always mean hitting your dates, getting paid, or receiving a promotion. Winning can be a simple, playful thing, “We were awesome as we kicked your ass.”

More importantly, BAB is a regular forum for experiencing that relationships are not defined just by the work we do together, but who we become with each other when we aren’t looking.

A Story Culture

The Editor and I don’t argue, we discuss.

We’re arguing… discussing over a glass of red wine my concern over our collective attention spans. Not just she and I, but everyone. The whole damned planet.

I say, “Information just keeps getting smaller. We’re sharing our bright ideas in 140 characters now and no one is taking the time to construct a strategic thought. All these micro-ideas are free and everyone is taking them for granted. We’re just tactically stumbling through a day full of intellectual sound bites stuffed with shortened URLs. There’s no deep now. Just shallow passing seconds.”

“No one is learning. There’s no work involved in knowing a thing, so we’re becoming mentally flabby. I want people to read more.”

To which the Editor retorts: “I don’t think you know what information is.”

Hmmmm.

Information has a Hierarchy

So I looked it up. According to Ray R. Larson at Berkeley, information has a hierarchy that looks like this:

• Data - The raw material of information
• Information — Data organized and presented by someone
• Knowledge — Information read, heard or seen and understood
• Wisdom — Distilled and integrated knowledge and understanding.

If you ignore the fact that the word information is used to define a hierarchy about information, this hierarchy makes sense, but it dances around a key point.

Another version of this hierarchy describes the same categories as above but focuses more on what happens to information once we get a hold of it. Not just consumption, but synthesis.

• Data — Raw material. Facts. Got it.
• Information - Organized data. See what happens here? Someone showed up and organized the data into something else. Why’d they do this? How’d they know it was the right thing to do? Let’s keep moving.
• Knowledge — Information seen, heard or read and understood. To me this is when information is transformed by the understanding of why. Our data is organized into information and that is passed onto someone else who can now recognize the value in the information and thinks, “Oh, wow. Now I understand how a trash compactor works. Slick.”
• Wisdom — Distilled, integrated knowledge and understanding. The idea here is that higher order constructions of information are based beyond our ability to consume, combine, evaluate, and interpret information. The information becomes a catalyst for creation. Think of it like this: maybe a lot of people understand trash compactors, but you know so much about trash compactors that you could build one yourself and perhaps advance the art of trash compacting in the process.

Still with me? This is going to take more than 140 characters and there’s a point. Just wait a tick.

Take a look at this list:

• New York is a city.
• It takes me about five hours to fly to New York.
• I’ve been to New York three times this year
• I never believe I’m in New York until I’m in a cab or smoking a cigarette.

Is this data, information, or knowledge? Or just four boring tweets? That would depend on whether or not you’re interested in my experiences in New York. But what I provide in this list is the opportunity for increasing amounts of understanding, and understanding is the progression through, and synthesis of, increasingly complex pieces of information. Right?

There’s another thread that ties this information together, and you may not initially see it, but if you’ve started mentally asking questions - Why does Rands go to New York? What does he do there? Did I know that he smoked? - you have started to find it.

I’ve begun to tell you a story.

A Shattered Narrative

The reason no one watches or cares about the evening news anymore is because there are a great many other ways to find your news. A weblog here, a Twitter status update there. In the deluge of information variety we’ve realized that the evening news is just one set of facts and just one carefully constructed story, and increasingly one with its own specific agenda. Who wants to be spoon-fed 30 minutes of ad-infested evening news when I can figure out what my world thinks is important by glancing at The Daily Show, Twitter, and NetNewsWire?

The traditional narrative has been shattered into bits of well-indexed information. Google wasn’t the first indexing tool, but it’s certainly the best. Still, Google is powerfully dumb. Yes, I can find whatever piece of information I’m looking for, but what’s more interesting are all the related pieces of information. How do you query for knowledge via Google? How about wisdom?

If you’re buying my definitions of the informational hierarchy, there’s no replacing the process of understanding if you want to delve into more interesting forms of information. There’s no replacing a human being combing through seemingly disparate pieces of information to evaluate, interpret, and combine it into something unexpected; into a new work. Into a story.

Those frustrated with Twitter are frustrated because they have a belief that a story needs a beginning, middle, and end. And that it should have all of those parts before it’s presented to them. What the hell am I supposed to learn from a tweet? The point of Twitter isn’t knowledge or understanding, it’s merely connective information tissue. It’s small bits of information carefully selected by those you’ve chosen to follow and its value isn’t in what they send, it’s how it fits into the story in your head. There are great stories to be found on Twitter, but you have to do the work.

This is what is going on all day. It will start with a random tweet about conferences and you’ll think, “I don’t understand why everyone goes to conferences”. You won’t act on this thought; you’ll leave it buried in your head until you see that link on del.icio.us where someone important rails on the lack of women presenters at conferences. And in that moment, you’ll remember that drunken thought you had at that conference last March when you discovered the basic truth about conferences: it’s not what you learn, it’s who you find.

From a disparate set of information, you continually find your own arc, your own story, and my question is: What are you going to do with it? You’re an information nerd, you’re adept at consuming massive amounts of micro-information, and those who watch you do this are saying you’ve got a short attention span, and you might.

But I think all this micro-information has macro-story potential.

Rands’ Story Hierarchy

As we’ve established, there’s information. Like everywhere. You, as a consumer of information, fall into one of three progressively complex buckets regarding this data:

• You can understand the information — What does it mean? Why is it important? How does it relate to other things I care about?
• You can explain the information to someone else — Hey Bob, this is what this means. I can explain it to you and impart my understanding.
• You can create more information, building something new and telling a story - Hey Jim, actually, we discovered a better way to do X. Bob and I were working on Y one time and realized that…

But Rands, I’m not a writer.

This is a poor excuse and the death of many a worthy story. The construction of a story has very little to do with writing. It has to do with the semi-magical process of you taking disparate pieces of information, combining them into something new, which includes your experience and understanding, and then giving them to someone else. Look around the walls of wherever you’re reading this and pick two random objects. Got ‘em? Ok, now tell me how they relate. No, you can’t say, “They’re both in the coffee shop”. What’s the first novel thing that crosses your mind about the intersection of these two items?

But you don’t have a story, yet. Just like information isn’t knowledge until it’s understood, your tale isn’t a story until you give it someone else — until they have a chance to see what they think about your inspiration.

But Rands, my thought is really, really stupid.

I understand what you’re saying but I don’t think that’s what you mean. I think what you’re saying is, “I don’t think that anyone will find anything of value in my thought,” and you’re wrong. You’ve got two things going for you. You’ve got the inexplicable moment of inspiration that created your idea, and it’s the closest thing to magic you’ll experience in your life. Second, you’ve got the entire planet listening and there’s just no telling what any of those folks are looking for.

The value of the idea is one part that it is yours and one part that you gave it to someone else. It’s you and something new.

Information Is Getting Smaller and Faster

Look at the historic progression of popular personal written information containers over the past 10+ years:

Home pages > Blogs > Lists of Links > Tumblr > Twitter

I see two symbiotic trends. First, I see a reduction in the average size of a piece of information. I see information that feeds our short attention spans. Second, and more important, I see our tools increasingly removing barriers from producing information. Remember when you needed a nerd friend to set up a weblog? Did you have any issue figuring out how to publish a thought with Twitter? I hope not.

Yes, these frictionless tools make it so anyone can say anything about any topic, but these tools are built with you in mind and I do mean you. Imagine if Twitter forced you to follow certain people. What if Facebook randomly added folks to your friends list? You know what you’d have? The evening news. Random stories from folks you don’t know and probably don’t trust.

We’re in a share everything world and you get to choose your role. You can be overwhelmed and sit in the coffee shop with your friends and say, “Twitter: what’s the point?” Or, you can jump in with both feet, grab those three random ideas and tie them into a story that no one has ever seen.

An Essential Skill

I wrote, edited, and published an entire book without physically interacting with a single person at my publisher. The t-shirt I produced last year and the one I’m doing this year were entirely designed, developed, and shipped by interacting with two different organizations that I never met. Paradoxically, it’s never been easier to share or meaningfully interact with more people with less physical, in-person effort.

Your ability to compose and convey information as well as express yourself through your fingertips is a skill that is only going to increase — and increase in value — as people become more comfortable with their place in communities that span the planet, and as the tools to connect them become more commonplace.

In this digitally distant world full of information that appears to only be moving faster and faster, you get to choose: how much will I consume and how much will I create?

Up to Nothing

In Silicon Valley, you burn a lot of calories.

It’s not just the daily burn of your gig, it’s everything else involved in staying afloat in a valley which is constantly reinventing itself. You sign up for every new service and spend the prerequisite 3.7 minutes to determine “Does this matter?” You surf the web, you tweet, you update your Facebook, all of which brings a constant flood of new data that needs to be sifted, sorted, and assessed.

You have compatriots in this caloric consumption. They randomly walk into your office or your life and with them they bring additional reasons to burn more calories. Have you seen this? You have to try it. In fact, I’m not leaving until you’re jumping up and down excited about this very important thing.

We are part of an industry that is addicted to enthusiasm, to getting things done, and discovering the new, but sometimes the right move is stopping and putting this world on hold. You need to learn how to build quiet moments of nothing as a measure of balance.

… Which is why I go to a bookstore.

An Essential Exercise in Inactivity

The moment I walk into a bookstore I remember what I love about them. They are an oasis of intellectual calm. Perhaps it’s the potential of all the ideas hidden behind those delicious covers. Or perhaps it’s the social reverence for the library-like quiet — you don’t yell in a bookstore, you’ll piss off the books.

A bookstore is where I rediscover that while I might be addicted to the non-stop calorie burning Silicon Valley lifestyle, I also need the serenity only found in the deep quiet of the consideration of nothing. Considering nothing takes work and practice, and the act contains a contradiction: the more I think about what I need to do, the less I’ll discover the thing that I don’t know that I’m looking for.

It’s confusing, but you need these skills because you have days full of somethings. Your day is probably spent at one of two sides of a spectrum. You’re either reacting to whatever is showing up on your doorstep or you’re proactively looking for new things to place on your doorstep so you can figure out what to do with them. Reactive. Proactive. It’s how you spend your entire day.

Excursions to the bookstore are essential exercises in inactivity where the whole world stops being a thing to do.

My most recent trip to my local Borders was in the middle of a two-week period where I’d spent time in both Tokyo and London. Forty hours of flying resulting in five days of meetings which required constant thought, creativity, and focus. During a brief stint back in normality in the States, I had instructions to acquire a children’s book for a nephew.

Now.

The children’s book section at my local Border’s has been voted “Most Likely to be a Total Fucking Disaster” for three years running. Combining this unique cluttered chaos with a head full of jetlag means my head is overflowing with disorganized somethings and I’m predisposed to be annoyed. Even worse, I’m not looking for a specific book. I’m running on “get something he’d like” orders, which means I need a modicum of inspiration in order to be successful.

I need to discard everything in my head that’s preventing me from looking and being inspired.

This is a surprisingly hard mental maneuver because you and I are both used to days that are not only full, but full with well-defined things to do. A lack of structure, direction, and measures throws your brain into fits and this usually when I throw my hands up in frustration and walk out of the bookstore. My brain is rejecting the unstructured ambiguity involved in the search for the unknown.

Look in my head when I start: Where I am? This looks like the children’s section, but this part is full of toys and I need books. I haven’t read a good book in forever. Ok, keep moving until something looks right. Since when did they sell candy at a bookstore? Edward Cullen Sweet Tarts? Please. You know, I don’t even know what day it is. Ok, dinosaurs, he likes dinosaurs. Wait, can he read?

My analysis is: “this place is fucking confusing” and I think I’m talking about the bookstore, but I’m actually talking about my brain.

Up To Nothing

Go back to work and think about your average day. How often are you not clear what you’re doing? How often is the goal of the next 30 minutes completely undefined? Yes, you’ve suffered through meetings where there was no clear agenda and you felt like you were wasting your time, but that’s still a known quantity — I’m currently in the poorly run meeting scenario. Been there, done that.

What happens when there is no meeting, no burning task, no one in your office? You wander, you surf the web, you stare at that calendar on the wall and think, “Why do we have leap years again? I forget.” And then you feel bad. I should be working. I should be doing something. They’re not paying me to reverse engineer leap years. I have things to do.

You’ve built this guilt into your office. It’s why your screen is not facing folks who walk through your door. You’re worried: “They might see me doing nothing”.

You’re not up to nothing. You’re aimlessly mentally wandering — an act made famous by every bright idea ever had in the shower. Think of that moment. Your body is busily on task with the cleaning and what does your brain do? Sure, if you’re stressed about layoffs, you’re going to worry about layoffs, but those mornings when nothing is pressing — what happens?

Your brain builds something from whatever mental flotsam and jetsam is in your head. Perhaps it’s a useful thing, an answer to a question you didn’t know you needed. Perhaps it’s just an interesting combination of thoughts put into a story. It’s dreaming, but you’re awake.

Back to the bookstore. Remember my orders, a good book for the nephew…

If I survive the mental rejection of ambiguity, the next moment I need is one of discovery. In order to ground myself in the silence, I need to discover a single bright and shiny thing and there’s absolutely no telling what that thing is until it shows up. It might be based on my mood, the last ten things I cared about, a random word someone said to me, my favorite color… the list is endless, indefinable, and entirely locked in my head.

But there is nothing ambiguous or unclear about the discovery. It’s obvious. It fills an immediate gap I did not know I had.

In this bookstore excursion, it’s a black book. It’s odd to see a black book in the endless rainbow of the children’s section, but there it is. Black cover with masking tape surrounding what looks like a handwritten title: Wreck This Journal. Ok, interesting. I flip the book open to the handwritten instructions:

1. Carry this with you everywhere you go.
2. Follow the instructions on every page.
3. Order is not important.
4. Instructions are open to interpretation.
5. Experiment. (Work against your better judgment)

And there it. Exactly what I needed. A reminder of why I go to the bookstore in the first place — to mentally stumble around, defying my better judgment, in a nourishing environment of nothing.

Wreck This Journal was created by Keri Smith, who calls herself a guerilla artist, and I’ve no idea what her book is doing in the clutter of the children section. It’s a journal dedicated to its own destruction. One pages instructs you to Rub Dirt Here. Another asks you to scribble wildly using only borrowed pens (document where they were borrowed from). The journal is full of ideas to create unstructured moments of seemingly meaningless activity designed to get you to stop and let something else in.

Don’t Look For It

Stop and let something else in. It’s a confusing skill, which starts with a question: how are you going to find what you don’t know you need by not looking for it?

A day in high tech rarely encourages the activity of doing nothing. Nothing is not cost effective. Nothing is not something you’ll put in your review. Nothing gets a bad rap and the more I attempt to define it, the less useful it will be to you because what I need out of nothing is different than you.

Moments of nothing are not moments of creativity or consideration. (They might be.) These moments don’t last long because your brain can’t sit still; it’s been trained to burn calories all the time. (The longer it sits still, the better.)

Your brain instinctively and naturally attempts to build something given whatever world it’s currently in. In a bookstore, with effort, I can shed the somethings of my everyday and find the nothing that I don’t know I’m looking for. (And that rules.)

The Foamy Rules for Rabid Tools

The brother-in-law lives in the ‘burbs and needed five trees removed. Not big trees — 10 to 15 feet tall, six-inch trunks. Not a problem.

I live on the edge of a redwood forest in Northern California. There are sturdy oaks, playful maples, lovely madrones, weed-like bay laurels, and, of course, giant redwoods. But the pleasure of living in a forest has a tax. Trees fall and trees die, and in a forest of any significant size, this is always happening.

You need a chainsaw. In my case, I need three. There’s Junior, who is great at handling the small jobs. He’s light and ladder friendly.

Then there’s Marty. He’s the everyday mid-sized saw that is enough to handle almost any job. Marty would be perfect for a job in the ‘burbs.

Last, there’s the Rocket. Any tree is the Rocket’s nemesis.

Even if you’ve never handled a chainsaw, you’ve probably used a handsaw. It’s a physical, grinding affair. It’s fun for about three minutes and then you start wondering… am I making progress? The brother-in-law had taken it on himself to use a handsaw on one of the trees. In his three minutes he’d sawed off… a branch.

When Marty and I showed up, we dropped all five trees, cut up the trunks and branches, and stacked them into disposable piles in an hour.

The lesson: the correct tool is exponentially more productive.

That’s a long introduction to say an obvious thing, but I’m going to make it even longer. Take a moment and step inside the mind of the brother-in-law. I’ve got several trees I want to get rid of… and what do I have in the garage? Two hammers, a paint can full of nails, some leftover wood and… a saw. Perfect. A saw.

Context shapes perspective, so thanks to the contents of his garage, he knows of no universe where there are chainsaws. He’s heard of them and suspects they’re much faster than the laborious sweaty grind of this sawing, but there’s no chainsaw here, so he’s semi-happily hacking away. To me, standing there with my arsenal of chainsaws, it’s absurd. It’s a criminal waste of his time.

The lesson again: the correct tool is going to make you exponentially more productive.

The Foamy Rules

As an engineer, there is a short list of tools that you must be rabid about. Rabid. Foaming at the mouth crazy.

This is an obvious list of tools and there’s nothing here that you haven’t heard before. The news is that you need to care. You need to be able to explain in great detail why using green-colored text on a black background is THE ONLY WAY TO CODE. You need to be a zealot about your tools and zealotry starts with fit.

I was a database guy then I was a shrink-wrap guy and then I became a web applications guy. Each of those professions came with their own set of bright and shiny tools, but the tools were not important. Even a specific feature inside of that tool is not that interesting. I believe you can be just as productive sitting inside of a rich development environment such as Xcode as you can inside of TextMate and a slew of terminal windows. The point is not which tool, the point is that the way that tool - your tool — looks, feels, and functions fits how you see, move, and work.

These are my foamy rules and they may differ wildly from your list. That’s cool. My development experience is different than yours. I started working with computers before the mouse which means I trust my keyboard more. Integrated debuggers had just landed when I began developing which means, yeah, I like debugging at the command line. Again, the point is to get foamy, because what makes you foamy makes you your best.

My foamy rules:

My tools appear deceptively simple. TextMate. Terminal. Transmit, LaunchBar, DropBox. The mean time to get one of those tools set up is just a few minutes. I can build out my development environment on a new machine in a half-hour. This has a couple of handy implications. My tools are readily available and lightweight. I can download and install everything except for an operating system in a short amount of time. Similarly, setup and configuration of these tools is close to zero.

You might think this setup means I’m expecting my computer to randomly explode. No. These tools are not simple; they are well-tuned. A TextMate user knows it’s an onion application. You can keep pulling back the layers and finding new functionality, which is going to make your development experience faster. The same goes for Terminal and LaunchBar. The base functionality just works and if you have a particular development itch you want to scratch, the tool can scratch it.

My tools do not care where my work is. How many times have you experienced this? You write a quick script on your local machine to do something clever. You fine tune it and then plop it on your server and rediscover the rule — there’s nothing quite like production.

Any tool that does not allow me to develop live in production is slowing me down. When someone showed me how to set up Transmit to do editing on remote files, I saw hours of heretofore unknown production debugging issues vanish.

Yes, editing locally is fast, especially when you live on the edge of a redwood forest where DSL latency blows, but a tool which doesn’t allow me to develop over the wire isn’t a tool, it’s a debilitating hindrance.

Rands, edit? In production? Are you insane?

No. The tangential background rule is: “If you don’t know what you’re doing in production, you don’t belong there”.

There’s a corollary, which is: “I don’t care where my work is”. This is recent foaminess brought on by Dropbox. For non-production work, like, say, writing a book, I don’t want to think about where the most recent version of the work is sitting. Yes, I’m talking about version control — but shh, don’t call it version control — just call it Dropbox. Providing I have a network connection, this tool magically refreshes a shared directory sitting on each of my machines. I can’t think of the last time I worried about which version of a document I was on, and that means I’m spending more time working than worrying.

My tools are designed to remove repetitive motion. One of my first algorithmic holy shits was during my second computer science class as we were learning sorting algorithms. The professor elegantly walked us through the construction of different algorithms, explaining the pros and the cons, and then he landed Quicksort. Holy shit.

It wasn’t just the elegance. It wasn’t the recursive simplicity, it was the discovery that with imagination there were approaches that were wildly more efficient — and simpler. Whether you’re formally trained as a computer science nerd or not, you’ve learned the value of efficiency — to make each action that you take mean something. You know that when you’re efficient, you have more time to do what you love.

This is why I have a simple requirement that any tool I rely on has complete keyboard support. I will fall back on the using the mouse for one-off activities, but for any action I take that I know I’m going to do again, my question is, “How do I make this action cost less?”

Think of it like this. What if I told you that each time you wanted to save a file, you had to stand up, climb up on your chair, and jump up and down, yelling, “I would like to save my stuff now!” The first time you had to do it, it’d be kind’a fun, but after that it’d drive you bat shit crazy. It’s a similar feeling each time I reach for my mouse. I feel I’m engaging in an unnecessary task, which is always going to waste my time, because with a mouse sometimes you miss and missing is a tremendous waste of time.

Finding any file or application is, ideally, four keystrokes. Cmd-Space (LaunchBar), Letter #1, Letter #2, Return. Sometimes I get lucky; sometimes it’s three and you know that puts a smile on my face every single time it happens.

My tools only do what I’ve told them to do. Back when Dreamweaver first landed, I wanted to love it. I was so tired of the repetitive motion of developing HTML pages and the idea of a tool that was going to visually handle that laborious process was appealing. Problem was, Dreamweaver changed my code… without asking.

It what?

Dreamweaver was attempting to be helpful, but the moment it reformatted my code, I threw a fit. YOU TOUCHED MY CODE. Dreamweaver never recovered from that horrendous first impression.

My impression and my opinion of robust integrated development environments is that they can do a lot of good in terms of helping you visualize what the hell is going on. Borland developed some of the best environments for building code back in the day, but I still find myself with extremely primitive development environments where I’m tweaking code in TextMate and debugging inside of a couple of Terminal windows.

Yeah, I know all about the glory of integrated debugging and I see all you Eclipse guys having a ball, but what I found in many years of development is that embracing the fancy tools means spending time tinkering with your tools to get them to behave how you want.

The corollary to this rule is: “My tools don’t have a lot of moving parts”. Dreamweaver-grade code offenses are few and far between with solid development tools, but the fancy still comes with a cost. You may be fully willing and foamy to embrace that cost, but I’m not.

Am I more efficient than you? Maybe. Do I know where I stand relative to my tools? Yes. Do I have to relearn my development process when the people behind an elegant tool shoot for more elegance? Nope.

My tools are my tools. Choosing a thing makes it yours. The choice is the result of that unique mix of logic, superstition, stubbornness, and experience that fits you.

You read that right. Green text. Black background. I’ll tell you why right now. I’m an old school DOS guy. My first word processor was Wordstar and that’s the word processing program I came to associate with the fugue-like state of maximum productivity: the Zone. This is why I continue to favor colored text on a black background in my current favorite editor, Textmate. The coloring reminds me of an primal safe place where the tool is serving its purpose — to get the hell out of the way so I can go be exponentially more productive.

This is why, as engineers, we stick with something that works for us. This is why the ancient likes of vi and Emacs continue to flourish. Once we find a tool that works for us, once we’ve chosen that tool, it becomes ours and remains ours. It allows us to get foamy.

An Evolving Foaminess

My brother-in-law doesn’t need a chainsaw. When I took out his five trees, I eliminated half of the population of trees on his property. While a chainsaw is a delicious combination of sound, power, and sawdust, my brother-in-law didn’t choose a home where the trees are on the offensive, so he doesn’t need defensive weaponry.

He does need to know about a universe where chainsaws exist because every moment of his time is valuable. What differentiates us from the monkeys is not our ability to pick the right tool for the right job, but to pick the best tool.

And you never stop looking — this is why the last foamy rule is the most important: my tools are always fighting for their life.

My current tool set is influenced by all of my experience. Yeah, the elegant simplicity of vi is attractive to me — it reminds me of the uncomplicated early days of development, but vi can’t compete with the holy shit I experienced when I first ran into TextMate. This tool is always five steps ahead of me. I love that.

But TextMate, like all of my tools, must evolve.

Try this right now. Stand up and walk into the office of the best developer in the building. I promise two things: they will be happy to, at length, foamily show you their development set-up and you are guaranteed to learn, at least, one thing about moving faster. Perhaps it’s a tool you’ve never heard of or maybe it’s the way they deftly manage a tool you’ve taken for granted.

I don’t know what you’re going to learn, but I do know you’ll see one thing that will instantly and obviously make your universe a smaller, more productive place.

(c) 2002-2012 Rands  (Something witty)