I absolutely loved that thing, especially by contrast with the rest of my life. School was typically dull: I spent very little time learning about anything that was important to me. I think I could count the number of friends I had with half of one hand – and they were certainly outnumbered by people who disliked me but couldn’t find constructive ways to express those feelings. My home life was no picnic, either.

Yet none of that mattered when I was at the keyboard of my Mac. It was, all at once, a second school, a conduit to another world, an infinitely deep toolbox and a magic wand of indescribable power – running at 60 MHz.

I thought it would be fun to venture down memory lane and revisit my Mac of 1995. Of course, the hardware itself is long gone. But through the magic of Sheepshaver, I’ve been cobbling together the scraps of my favorite childhood memories. Other kids had sports, comic books or Jesus. But the thing I believed in was my Mac.

System 7.5

My childhood experience with the Mac spanned System 6 through Mac OS X 10.2 but System 7.5 was easily the golden age. That would be the first time I had long-term access to a machine I could customize any way I wanted.

Once installed in Sheepshaver, even through an emulated PowerPC processor, System 7.5 is extremely performant compared to 16 years ago. On a Late 2010 MacBook Pro, loading from an SSD, boot time is about two seconds, compared to about 30 seconds in 1995.

The cheerful parade of Extensions and Control Panels marches at the bottom edge of the screen. Performance be damned, I loved collecting these.

Of course, the System 7.5 era was extremely long – an interminable wait for Copland, the next generation operating system that would make unicorns fly from your 4x CD-ROM drive. As time went on, the UI started to look pretty stale.

So it’s important to install one of my favorite extensions from the period, called Aaron, to spruce things up a little:

That’s better. Aaron adds a little flair and dimension to the otherwise flat and bland System 7-era UI and I liked it a lot better. Even at 10, I was starting to be curious about the nuances in UI design.

AOL

AOL was my very first taste of the internet. I believe our first bill came out to $80. So that didn’t last long. Luckily, their unlimited dialup service showed up about a year later, so I would be back in action. Sadly, but unsurprisingly, you can’t actually use the AOL client anymore. Still, I got to poke around with the modem configuration panel that was a frequent source of frustration once upon a time.

ClarisWorks

This little suite was bundled with the Performa. Very little to be excited about here but I spent so many hours cranking out school reports and other projects in its Word Processing, Paint and Vector Art modules.

Hotline

The gravest of my youthful indiscretions was easily my voracious appetite for pirated software. Enter Hotline. Before Napster, before Gnutella, before BitTorrent, there was Hotline. Hotline let anyone set up a file server on their home computer. It included chat, BBS and persistent user accounts, too. Vibrant communities sprung up around these little amateur servers. They dedicated themselves to everything from religious evangelism to technical support to sharing anarchist/conspiracy text files. Of course, being the internet, there would be plenty of pirated software in the mix.

To my utter delight, the mid-90′s version of Hotline I got started with so many years ago not only still works, there’s even a handful of servers still in operation. Back then, I was lucky to pull down files at 2.8 KB/sec via dialup. A limitation of either Sheepshaver or Open Transport, the aged TCP/IP stack Hotline uses, now caps me at 60 KB/sec, but that’s a big improvement I’d have killed for as a kid.

Hotline is a major hinge in my history. With access to so much software, I dedicated myself to learning how to use it. I rarely had access to any documentation beyond what was built into the apps so it was often an exercise in trial and error. It was also fun beyond words.

This began my life-long study of interfaces and user experience. If this hadn’t happened, I have absolutely no idea what I’d be doing with my life right now.

Photoshop

Hotline could be extended with customized icon sets. If one of the two dozen included user icons didn’t strike your fancy, you could create your own. The trouble was that only other users with your custom icon file could see your handiwork.

Of the thousands of active Hotline servers in operation during its golden age, two emerged as dominant tribes vying for the loyalty and patronage of the masses. Known as BadMoon and SoSueMe, the servers collected thousands of customized user icons and then distributed them as authoritative custom icon sets.

Of course, I wanted to get in on this. ClarisWorks’s Paint module really wasn’t up to the task, so I had to find and learn Photoshop 3.0. This little head-start on graphics tools ended up being important – years later, I’d be able to design my own UI elements thanks to this early noodling.

It meant days of downloading but it was worth it.

One striking thing about Photoshop 3.0 is how very little has changed after all this time. The color picker is identical. There are the many cluttery pallets for layers, brush diameter, colors, and channels. Later versions would introduce layer styles, which were awesome but a little rigid, and endless other bits of junk. The overall workflow, aside from crappy Save For Web, remains much the same. (This is why I now use Opacity to design UI – it’s built for how I actually work.)

ResEdit

I loved ResEdit when I was a kid. Apple’s resource editor let you poke your nose into most system files and applications, revealing image assets, icons, interface elements and plenty of other technical goodies I didn’t really grok at the time. It was surprisingly deep, including a little MacPaint-like editor for the icon files along with a drag-and-drop interface editor. At the instigation of David Pogue and Joseph Schorr, I recall using it to make the bloated trash can look filthy and overflowing.

Gaming

No exploration of Mac history would be complete without a look at some of the platform’s greater gems of gaming. PC’s may have had more games by volume but the Mac didn’t have any shortage of fun, either.

Escape Velocity

I sunk so many hours into EV, it’s not even funny. A nerd who grew up on Star Trek and other scifi, I found this game’s premise of space exploration, commodity trading, secret missions and interstellar combat extremely compelling. Entire Saturdays vanished into its gaping maw.

Marathon 2

Before Halo, Bungie made Marathon. It was a rich story of treachery and tragedy among the stars. Crazy AIs and three-eye aliens all trying to get you killed while you blast things with enormous guns. No full-motion video cinematics here, though. If you wanted story, you had to read.

SimCity 2000

I was terrible at SimCity. My budget rarely balanced, my people always complained.

I loved it anyway. SimCity 2000 is still surprisingly playable, too. Definitely a timeless piece of work.

End of an Era

The way many expected the System 7.5 era to end was pretty bleak: Apple collapses, the Mac dies, and its software and hardware begin to decay into uselessness.

Of course, history went a different way. I’m glad that Apple survived long enough to ship Mac OS 7.6 and OS 8, that in the time since Apple has rebuilt itself into the juggernaut of its industry. Mac OS X beats the hell out of anything that came before it. I still remember picking up my copy of Macworld at the supermarket and learning how Apple bought NeXT – and hoping that the future would bring brighter days for everyone’s favorite “beleaguered” company. And it did.

Still, I’ll always look back with fondness on those days of innocence before a Unix shell was a keystroke away, before every UI interaction was beautifully animated, before we measured even the tiniest of hard drives in gigabytes, before collaborative multi-tasking and protected memory. When using the computer was new and exhilarating. When the Mac was more than just tool – when it was an escape to another realm of existence. Those were the days when a little boy, without coming anywhere close to realizing it, laid the groundwork for all the wonderfully fun things he’d get to do years later as a man. I learned way more from my Mac than school ever gave me.

Thanks for the memories, Apple.

If you need more detail, here’s the deal.

Once, when I was 17, I picked up a girl and took her out on what I hoped was a date (in case you’re wondering, it wasn’t). About ten minutes into the evening, as we drove down the highway, a police officer pulled us over.

I was speeding. 10 MPH over the limit.

It cost me $134.

Being 17, the lesson I learned wasn’t “Hey, maybe I shouldn’t speed.” Instead, I decided “I need to figure out how to get away with it next time.”

And I did. Reading many sources, talking to a cop who worked with me at Best Buy, and trying things out later, I figured out what to do. In the eight years since my first ticket, no one has given me another one. It helps I don’t drive like an idiot anymore. But even the best drivers can lose track of the speed limit.

The following guide assumes that you’ve been pulled over by the police and the maximum extent of your crime is a traffic infraction. Maybe your stop could have been more complete, maybe you lost track of your speed. This may not help you if you’ve done anything worse than that. Driving drunk? Got some pot in your car? Illegal weapons? Involved in anything else that the police won’t be impressed with? If any of those is a yes, this probably isn’t the guide for you.

Let’s also be clear: I am not a lawyer and the following is not legal advice.

Still with me? Okay, you’re otherwise law-abiding but you did something naughty in traffic and the police noticed:

Take a Deep Breath

You’re about to enter a situation with a distinct asymmetry of power. If you’re not used to that, you might be nervous or intimidated. Don’t be. In the grand scheme of things, you’ve done very little wrong. Take a very deep breath, relax and gather yourself.

Regardless of how lopsided this interaction is going to be, remember one thing: the police officer is a human being, just like you. Your cop might be mean, might be nice, might be a mom, might be nuts about astronomy, might be going through a divorce. Each is their own person, so discard your preconceptions and do your best to understand the challenges they’re facing.

Pick a Safe Place to Pull Over

The police want to talk to you. They’re going to need a few minutes to do it. Make sure you give them a good spot to work with. If you put them in a place where they’re on edge because of unsafe traffic conditions, you’re already on their shitlist.

Surrender

Being a cop is hard, scary shit. They don’t know if you’re speeding because you’re oblivious or because you’re on the run. As an officer emerges from their car, they have to prepare themselves for trouble. You could be a desperate criminal, ready to kill or maim them to secure your own freedom. Imagine it from their perspective: this is not a fun moment for you but it’s worse for them because they have a lot more uncertainty to grapple with. At least you know what’s about to happen.

Roll down every automatic window in your car. Especially if you have tinted windows, this lets the police see exactly what’s going on inside the vehicle. A backpack, an In-N-Out cup, a water bottle, say. Okay. No big deal. Not scary. Much better than a dufflebag full of drugs, a weapon, or worst of all, an unexpected group of armed bad guys.

You have nothing to hide, so show instead of tell.

As the police approach, make sure you and your passengers rest their hands on the rim of the car’s windows, in plain view of the police. If they can see your hands from several feet away, you’ve spared them several seconds of adrenal windup. They’re more likely to be relaxed, which means they’re more likely to be friendly.

Turn off your car. For bonus points, place your keys on the dash. A car can be a dreadful weapon all on its own.

The goal during the approach is to make sure your cop knows that there is absolutely no reason to be tense or concerned about what’s about to happen. You’re harmless.

Now it’s time to talk.

Don’t Be an Asshole

Remember you’re about to talk to someone who has one of the hardest, most thankless jobs in the world. You enter the conversation worried about points on your license and paying a ticket. They’re worried about never seeing their families again.

Keep your hands on your window ledge and greet the officer as they approach. A cheerful “Good evening, officer” is all you need. Do not be terse, do not be curt, do not be rude. Just say hi.

Follow the officer’s lead. If they want to talk to you about why they pulled you over, they will. You’ll get nowhere by being demandy about the reason. Many times, they’ll just start by asking you for your papers – “license and registration.” Sometimes they want to see insurance instead of registration. I don’t know what influences this. Wherever the conversation goes, be polite and courteous. Show, through your behavior, you’re just a normal person who missed a road sign.

If asked why you’re behaving this way, tell the truth: “You have a hard job, officer. I do, too, so I’m just doing my best to make this easy on you.” Cops deal with a lot of inconsiderate people, so you don’t have to do much to stand out.

It’s very likely that you’re going to have to reach into your pocket or the glove box to comply with an officer’s requests. Announce your intention to do this before moving your hand. “If it’s all right with you, I’m going to move my right hand to the glovebox. My registration is in there.”

While one hand digs around, keep the other firmly planted on the steering wheel, in clear view. After you’ve retrieved whatever you were asked for, hand it over slowly and make sure your hands return to the dashboard or the window ledge. If you forget, your cop will remind you.

The police may ask you if you know why you were pulled over. Many people will tell you that it’s in your interest to play dumb here. I don’t work that way.

See, I don’t like to lie. It’s a pain in the ass. When, for example, two Texas Highway Patrolmen pulled me over a few summers ago, I knew why I was speeding. When asked, I told them.

“I’ll be honest with you, gentlemen. There was a feedlot back there. Thousands of cows! It smelled terrible, honestly. So yeah, I hit the gas because it was making me ill and I needed to get out of there.”

So yes, I waived my fifth amendment right not to incriminate myself. I also made myself a human being. By being direct and honest about what’s going on, I’m hopefully sticking out as different from the sort of person they would usually ticket.

After a conversation, they sent me on my way with a warning. Let’s be clear: I’m hispanic. I didn’t look even remotely like the guys who pulled me over. I was about as thoroughly other as you can get while still speaking english. But I was considerate of the the patrolmen, I talked to them like human beings and they returned the favor by not screwing me with a ticket. I even pitched one of them on the company I was working for at the time.

A little empathy can go a long way. This has application in many other interactions unrelated to traffic violations or law enforcement, but I learned it here first thanks to the financial incentives involved.

We’re profitable, and we’re looking to hire a smart all-around programmer as our first hire. It’s a cliche, but we want people who like tackling complicated problems.

…

Depending on the task, we program in Ruby (on Rails), Javascript (a lot of this), PHP, Python, Objective-C (iPhone), and Java (Android). Flexibility is a plus.

…we like people who don’t put themselves in a box. You should be comfortable thinking about the product as a whole, and how changes are going to impact the hundreds of thousands of people who use it regularly.

…

We’re profitable, make the lives of hundreds of thousands of people better every month, have a rapidly expanding user base, and napping is an encouraged part of our corporate culture.

…

Basically, you’ll get to be the first employee of a small successful startup, while getting a paycheck and equity, and feeling good about the impact you’re having on the world.

It’s so clear. I know what kind of person they’re looking for, I know what’s special about their company, I can start to picture what it would be like to work there. Without having to say much about their people or product, I can tell one thing right away: these are not bozos.

There are no buzzwords, no vague claims about the company, nothing unclear about the kind of person they’re looking for. These are the kind of people you would feel comfortable working with because they’re direct and human.

And hey, did you notice they’re profitable?

It’s a good pitch because within the confines of their stealth approach, it tells you everything you’d want to know without handwaving or hyperbole. For respecting your intelligence, it stands out. It builds confidence.

This is a rarity in tech companies. Other job postings are not so clear. Try this one:

The Front-End Architect will be a senior and leading member of the [Product name] development team and will be responsible for driving innovative consumer applications. The FE Architect will help make technology decisions, lead, design/architect, implement and mentor.

I just picked this one at random off of craigslist. It was the first one I clicked. How can you be both senior and leading? What does it mean to drive an innovative consumer app? What makes it innovative? What will they lead, what will they architect? Of course, it wouldn’t be a bullshit job posting without some poor bastard having to “implement” something.

These people have no idea what problem their hiring is supposed to solve.

Job postings are a great window into a company. They show you just how much clear thinking is demanded  along with how well people communicate. Those are two important factors for working with other people. What about more consciously public communications?

Let’s turn to the granddaddy of software development:

Windows Phone 7: A Fresh Start for the Smartphone

The Phone Delivers a New User Experience by Integrating the Things Users Really Want to Do, Creating a Balance Between Getting Work Done and Having Fun

That’s a headline and sub-head from a press release. (Thanks, DF)

What the hell does any of it mean? What do users really want to do? Absent Robbie Bach and J. Allard, I don’t trust the word “fun” anywhere in a new product announcement from Microsoft, either. They probably mean an optional Comic Sans UI.

Maybe they’re going to clarify in the first paragraph. I’m just being a dick with their opener, I’m sure.

The goal for Microsoft’s latest smartphone is an ambitious one: to deliver a phone that truly integrates the things people really want to do, puts those things right in front of them, and either lets them get finished quickly or immerses them in the experience they were seeking.

I’m missing the ambition here. It sounds like their goal is to create a hierarchical mobile user experience optimized for short bursts of interaction.

Which is what everyone else does.

They haven’t described anything that sounds even remotely like a “fresh start for the smartphone.” What they’ve got is a fresh start for Windows Mobile that brings it up to par with the last three years of mobile OS evolution. By all accounts, they’ve succeeded.

Also, what the hell have they actually built?

The much more interesting story here would be owning the fact that they fell behind, then dug in deep, then, wonder of wonders, finally met a ship date. I’m sure it wasn’t a small undertaking. But they want to convince me they, unique among all companies, have rebooted the smartphone concept.

Contrast that with Google, who, the other day, genuinely unveiled a chunk of the future:

We have developed technology for cars that can drive themselves.

Damn. Really?

Our automated cars use video cameras, radar sensors and a laser range finder to “see” other traffic, as well as detailed maps (which we collect using manually driven vehicles) to navigate the road ahead.

Nothing vague about that. It sounds like something out of science fiction. You could call your mom, read that to her, and she’d understand exactly what’s going on, maybe even share your excitement.

Who inspires more confidence: the bullshitters or the straight-talkers? The problem with bullshitters is that they start convincing themselves that this is genuinely how people talk. They bullshit themselves. They lose the ability to communicate with any sort of clarity, making up for it in volume of words.

The best people respond to authentic communication. The best conversations form around genuine excitement from concrete performance. Clarity inspires confidence.

The big, suit-choked, sales-oriented, PR spinmonkey companies are a lost cause. There’s no reaching them. But you and me, we have a shot. Resist the siren song of saying words that mean nothing.

Look how much more powerful it is to be a real person.

I’ve hated Flash for the better part of five years, a bigotry mostly inspired by how poorly it has worked for me as an end-user. It’s even worse for people who need to maintain web sites in Flash, as I later learned professionally. An essential tool for any computer I use more than five minutes is Flashblock for Firefox or the outstanding ClickToFlash plugin for Safari.

Then it dawned on me: If I hate it this much, surely Adobe, who is responsible for maintaining it, must hate it even more. Surely no amount of money is worth this much pain, right? There must be another reason Adobe prolongs this shared internet misery.

Drawing equal parts inspiration from 2001, Terminator 2 and Babylon 5, I present to you: Flash is My Keeper.

Lego was an instant bullet train to any world I could imagine. Space ships, robots, lunar colonies, pirate treasures, ancient castles, you name it. These were mine to explore. I could spend days at a time perfecting some imaginary construct made real through the magic of Lego bricks and the exertion of my crude abilities. I treasured the rarer pieces, protecting closely my little snap-on magnet linkages and battery-driven light bricks. Regardless of whatever turbulent nonsense might have been happening elsewhere in my little world, Legos were an inviolable source of joy.

Joy, you know, that feeling that lives somewhere between the pit of your stomach and the tip of your smile. That vague something that builds a simple, contented glow inside of you that’s like a thousand perfect, extra-gravy-save-me-some-pie thanksgiving dinners with none of the bloated aftermath. Maybe you just saw the most beautiful vista in all of the world. Maybe you just fell in love. Maybe you’re ten years old and you see exactly what you were hoping for under the Christmas tree. You know what I’m saying, right?

Joy.

The Macintosh came a bit later. At age 7, I got my hands on a borrowed Macintosh SE. And the joy was there, too. It could do so many things. It could produce clean, perfect type that was huge! I made a lot of paper signs. It could store all of this information and then show it to me again later. It could show me pictures and organize them into this tidy scrapbook.

And sounds! It made all these noises. I was most enamored with the quacking duck.

It was this whole world inside there that I could barely understand. I knew only one thing for certain: I wanted more. So much more of it.

Eventually, through about three years of begging and cajoling, I convinced my mom to plunk down the tidy sum necessary to secure a Performa 6116CD for our exclusive home use. (The fact that I kept spending a lot of time at the home of a neighbor kid who had his own Mac and whom my mother intensely disliked probably sped things along, too.)

The 6116 was an even greater magnitude of joy. An 8x CD-ROM drive and a huge bundled library of multimedia content like encyclopedias and interactive atlases. Plus creativity applications and, wonder of wonders, Sim City 2000. I had so much fun exploring this new world. I spent an inordinate amount of time learning every piece of software I could get my hands on.

It was joy.

And then, I grew up. Like so many, I lost my capacity for the discovery of simple joy. It became the exception rather than the rule of life. Go to school, then go to work, do your job, go home, repeat.

Then I found programming. It occurred to me tonight, as I struggled, quite happily, to grasp how the hell it is block arguments in Ruby work, that I’d rediscovered a simple, consistent source of joy. Programming languages are infinite bins of Lego blocks, waiting to be assembled to my liking. Programming is a limitlessly fascinating Performa, waiting for me to learn and harness any language for any task I can imagine. There’s just so much to learn and enjoy in programming computers.

Even after a few years of it, programming makes me feel joyfully like a kid again.

The universal trial, of course, is money and I’m hardly exempt. There’s a sixty day delay between me making money from an iPhone app and Apple actually paying me. That leaves immediate, painful gaps in my cashflow.

The obvious solution to this is consulting — I’m privileged to know how to do a lot of things that are useful to people. Unfortunately, I’m still learning how to market, grow and manage that particular end of my business, so I’m painted into the most dread of corners: retail.

I live by the axiom that no honest man is too good for honest work. So while retail is often the dullest, most imagination free work you can do before hitting manual labor, that’s not the part that I hate most about my seasonal job.

No, the worst of it is this: I have to call my customers “guests.”

This is some of the most odious corporate newspeak bullshit in recent years. It has always irked me. Guest means a specific thing: certainly it implies hospitality, which may explain the intent, but it fails to properly convey the truth of the relationship between the store and the customer. Being the guest of another places the guest in the inferior position and the host in the superior position. While manners may require that hospitality be extended, being termed a guest in the final equation simply means that the customer does not belong there. It suggests they belong somewhere else.

This is the wrong view.

The customer is not a guest of the store. A successful retail experience means that the customer is at home in the store.

Somewhere, somehow, having “customers” became a distasteful condition for large corporations. This is unfortunate and I wish they would cut the crap. The truth is that there is honor in having customers. There is honor in upholding the sanctity of the customer relationship. Being a customer of a business means something very specific that no other English word can capture. Being a customer means being the lifeblood of a business. Being a customer means being the motive force behind a powerful organism that provides products, services, livelihoods and, ultimately, the basic existence of others. Being a customer is being part of a tradition that keeps babies nourished, families housed and people clothed.

That means something. Something potent. Something that must be continually venerated if we’re going to keep moving forward as rational people. Does any of this sound remotely like having a “guest” to you?

I’m proud to have customers. I’m proud to respect their importance to my business and their contribution to the fact that I’m not sleeping outside tonight. That is essential to my work ethic and it will never, ever change.

The end of my seasonal retail job can’t come fast enough. I’m not sure my teeth will survive the grinding required for me to get the word “guest” past my lips on every shift.

See the little movement lines, there on the left? They suggest the weird little dollar coin is moving from left to right. In western cultures (to whom the ad was targeted) left to right progression is associated with forward motion, while right to left progression signals backward motion. This something you’ll see in movies and comic strips if you’re looking for it. Here’s an example we all know and love:

The stylized arrow beside the word “Back” is pointing, appropriately, back, via a right-to-left perspective, while all of the letters in that word are also skewed right-to-left. The word “future,” conversely, is skewed left-to-right. It’s an instantly recognizable logo that succeeds by embodying its idea without whacking you over the head with it.

So look again:

Bing is talking about getting cash back, but illustrating their point by showing cash flowing away. This isn’t the economy to be talking about cash flowing away. I’m not sure that the dissonance this creates registers for most people but when it’s already unlikely that people will engage with your ad unit, the last thing you do is add subconscious resistance.

Yeah, it’s tiny, but the tiny things pile up into the enormous sand dunes that dog every last Microsoft endeavor with needless, unnecessary friction born of poor taste and obliviousness.

For more on this, enjoy a deconstruction of the hideous Bing logo.

But they called me. I had a job.

And I loved it. I’d never had more fun in my life. Thanks to a handful of adult mentors, I went from being shy and insecure in front of strangers to being outgoing, helpful and outrageously courteous, as befitted Publix’s customer service mission.  I got to meet people, learn about their lives and help make their day better, all in the time it took to bag up an order and pack in a car. Publix has a firm “no tipping!” policy and this was spelled out on a button affixed to my apron at all times. Despite this, not a week went by where a kindly retiree or harried but grateful parent didn’t stuff a couple bucks into my hand or pocket, buying me a sandwich or drink to end my shift. With a home life that was terrifyingly unpredictable and school that was tedious and unsatisfying, Publix, the people and the tangible benefits of my work there, became an escape that I craved.

There was plenty of reward in the fun of the job, but I found that throwing myself into my work with such gusto had other perks. When all of the front service clerks got reviews, there was much kvetching in the break room. Nickels and dimes, my teenaged colleagues moaned. They barely gave them anything for a raise. When my turn came, my boss, Mr. Starkey, called me into his office. After rattling through his estimate of my performance, I was given a fifty cent raise. It was the largest, Starkey confided, that anyone in my group had gotten. In retrospect, too, I realize that I was rarely tapped to do cleaning chores, since my management seemed to prefer me in front of customers as much as possible.

It was all so perfectly Randian, in a way that satisfied my then-Randroid brain. I gave honest effort in exchange for honest reward and recognition. Love your work, I thought as I pushed a pile of carts back into the store, and nothing feels like work.

Of course, it wouldn’t last. Home, as was its wont, took another lolloping, staggering jolt. For the second time in less than a year, we were moving away. Mr. Starkey was crestfallen. He’d been eager to groom me into cashiering and beyond. These were remarks that were and remain deeply flattering – it didn’t seem like he especially enjoyed terribly many of the other kids who had my title. At my request, he eagerly typed up a letter of recommendation. My favorite line, then and now:

“I would rehire him immediately if he were to return to Sarasota.”

I enjoyed it both for the heartfelt endorsement and for the tiny, whimsical implication that I was somehow in control of my existence.

I went on to be a salesman, an intern, a marketing manager and a project manager. With each job, I hoped to find the feeling I knew at Publix. The feeling of throwing myself into my work, enjoying every minute, and always hungry for more.

To be sure, I had some amazing jobs in the years since. Tremendous opportunities that provoked growth and change. But none of it could ever recapture the lost innocence of that first, magical time I worked at the supermarket. This realization, each time I started a new gig, was always a tiny disappointment.

For almost a decade, I’ve drawn a paycheck from someone. Until now. Not having been to the office, or any office, feels vaguely like retirement. Except there’s a ton of work to do.

And it’s back: that magic Publix feeling.

I love my new job. I’ve spent the last week building a new iPhone app from scratch. My new boss, me, really likes how it turned out. This is the most incredibly rewarding productive activity I have ever chosen for myself. The app is about done; I’ll have more to say about it soon. The most tremendous and powerful discovery came through its creation: I love developing applications for the iPhone. I can do it all day and night until my fingers hurt and still want more. It’s the most satisfying thing I’ve ever invested my working time doing. All I want is to get better and keep building.

Like Publix ten years ago, it doesn’t feel like work. It’s fun. It’s… wonderful.

Time will tell if this feeling and the products it creates will be sufficient to feed and house me. For now, I’ve got enough to hold out for awhile and give it everything I’ve got.

It’s a scary prospect to abandon security and regular cashflow, move across the country, and go into business for yourself, all the while hoping to hell everything will work out okay. Like many projects, it’s one of those things where if you truly took the time to consider all the attendant difficulty, complication and risk, you’d never bother to do it all.

It’s the best decision I’ve ever made.

There are no words to convey my excitement.

For as long as I’ve existed, there has always been an obligation to someone else’s rules lurking just beyond the horizon. Even on vacations, where time is theoretically mine, there was the lingering, ever-present knowledge that before I knew it, I would go back to a world of obliging someone else’s whims. For the first time, I’ll escape those bonds. It’s a feeling of freedom I’ve never known.

It must be stressed that while Full Sail has been a great place to work and I’m grateful for the experience, I had a job there and I have a handful of problems with working any “job,” no matter who supplies it. When I say job in this context, I mean any paid activity wherein you provide 40+ weekly hours in exchange for a regular paycheck, benefits and perhaps a reasonable approximation of social interaction. I’m a difficult, demanding, even impossible person, so these problems loom larger for me than perhaps they do you.

Ownership

When you arrive at your job and get down to the business of working, you are addressing problems that are not yours. These are the problems of whatever organization has hired you for your job. Depending on your level of career advancement and achievement, the problems you solve may range from the tedious (data entry) to the complicated (project or team management). No matter the complexity of your daily tasks, though, you can be assured that none of the problems they address are actually your own. While it is true that, through initiative, hard work and persistence, your handling of the organization’s problems can enrich your knowledge, experience and career prospects, this doesn’t change the fact that you’re doing someone else’s work.

Time

Unless you’re working at some sort of hippy, ultra-progressive company, you give 96% of your weeks to your job. That is a shitload of time. When I write it out like that, the egregious criminality of giving away that much of your life to someone who isn’t you seems so obvious, I can’t even come up with anything else to say.

Direction

I’ve spent a lifetime resenting any condition where someone else had authority to direct the discharge of my energies. The trade you make while collecting a paycheck is that in exchange for the money, someone gets to tell you what to do with 96% of your weeks. Even with the best boss, this deal is crap: Who wants to spend this much of their lives following orders?

Wealth

In the typical job arrangement, I would  show up each day and give a significant amount of time, energy, imagination and passion to the tasks of the organization. If I worked exceptionally hard while not being a douche and doing my best to help others be successful, I could earn promotions and more money. I would not become wealthy. Meanwhile, assuming successful management of the company, those who own the organization would increase their wealth. For many people, maintaining the wealth of others in exchange for a job’s security is a fine trade. That doesn’t work for me. If there’s anyone who should be wealthy off the sweat of my brow, I’m the first person on that list.

This is also including the assumption that whomever it is who owns the company is making the right decisions, which is absolutely not a given. There’s an illusion of security in a paycheck that comes crashing down as soon as layoffs or bankruptcy are announced (hello, domestic auto manufacturers). I’d rather have control of my fate than leave it in the hands of someone else.

Alignment of Interests

If your company did not need you, you would not exist there. This is a simple, business-driven reality and under no circumstances would I ever begrudge any organization this simple fact. Business is not and should not be charity. Still, think about it. The interest of the business is always and will always be the business. Never you, as an individual. This is an important fact to remember as you commit 96% of your weeks to the job that has hired you. You are the only person you can trust to have your own best interests as a top priority. Rest assured, if the business felt as though it could get more of your time while paying you less, it would surely take that arrangement. It’s just business.

The Game

You show up early, stay late. You take on extra projects and complete them in your spare time. You’re good to your coworkers and can always be relied upon in a pinch. Congratulations, you’re on your way to promotions and potential raises.

The trouble is, if you gave this level of effort for clients instead of your boss, you’d make a whole lot more money.

If you’re following the thread of my argument, you might be thinking “hey, wow, having a job is slavery and my company is screwing me over!”

Two things to note: Having a job gives you incredible opportunities to learn, grow and network while giving you the stability to develop yourself over the long term.

Secondly, unless you signed some sort of contract, you can leave any time you like. If you’re prepared.

So prepare yourself. Maybe I’m young and idealistic, but I firmly believe that the pursuit of things I genuinely love will bring me infinitely more reward than being paid to worry about someone else’s problems. I believe that dedicating the bulk of my time to my own growth, wealth and self-selected challenges, rather than to the development of someone else’s business, is the only conscionable use of my time. I believe that investing myself in an organization whose best interest is something that isn’t me would be to ignore one simple fact: I’m going to die one day. I need to make the most of my life and working for someone else isn’t going to cut it.

You may be following this, finding none of my assessments about having a job objectionable and thinking to yourself that I am, in fact, absurdly difficult and demanding. If that is so I salute you: your expectations for your life are much more easily satisfied.

I’m stuck wanting something else for myself. Thankfully, I’ve got some role models to help me handle this drive for a self-directed life.

Adam Savage

I heard Adam Savage give a talk where he mentioned that his line of work is mostly freelance. This perked up my ears. If you’ve spent any amount of time watching MythBusters, you know that Adam has a singular passion for the creative work that he does. He currently has the best job in the world because he desperately, obsessively craves the joy of making things. He’s incredibly good at it. I’m certain he never could have attained his world-class skills without first loving the work to begin with.

Nick Popovich, Super Repo Man

If you need a defaulted plane retrieved from a deadbeat, you call this guy. Nick had some flight skills and did his first repo on a whim. Now he owns a $20 million business grabbing planes from all corners of the globe. He’s good at it and he enjoys the work. Imagine the waste of his talents if he had stuck to being a traditional pilot and never realized his unique ability to resolve impossible, dangerous situations.

John Gruber

John is obsessive about details in design, typography, user experience and software development. He’s also obsessive about Apple. It shocks me that time and again, John is able to render completely accurate predictions about Apple’s direction and upcoming products. It’s a level of insight no one else on the web can match. It also puts professional investment analysts to shame. Is it incredible that six-figure salaried analysts can’t match the insight and prescience of a guy working from his home on a blog he maintains by himself? A little bit, but it should not be surprising at all. Only a love and passion for his subject matter could have made John the authority on all things Apple on the web.

My mom

I don’t know that she feels great about me saying so here, but it’s important to the legend: my mom didn’t finish high school or go to college. She does have a GED. She’s a minority for whom english is a second language. In pretty much all the ways a single mom can have the chips stacked against her, she had.

My mom loves animals – always has. It’s truly an obsession with her. In my childhood, I can recall the ownership of three ostriches, a donkey, six geese, dozens of chickens, an African Grey Parrot, dozens of dogs, some cats and multiple generations of coral reef tanks with tropical fish that made the house a viable field trip destination.

When I was very young, my mom took a certificate program at the New York School of Dog Grooming. To pay homage to James Herriot, no capped and gowned don ever looked back to his years among the spires of Oxford with more nostalgia than did my mother to her two months at NYSDG.

If I am difficult and demanding, then my mom truly is impossible. Nonetheless, she endured years of working for shitty bosses at shittier dog grooming shops. I don’t know how she did it, but one day, she had enough. I’m not sure where she got the funds, but she put together enough money to lease and renovate a commercial space, adding all of the kennels, baths, and other equipment necessary to provide absurdly clean, professional dog grooming services. For pretty much the rest of my childhood (and to this day), she was self-employed, her own boss. Despite the statistics for small business failure, my mom was and continues to be wildly successful at her trade without any training in business, marketing or finance. She doesn’t need it: she’s just incredibly good at what she does, wanted to provide the best possible service and has always loved her work. Not many other people can offer this. This was enough to ensure I never went hungry as a kid.

The message is clear: if you love the work you do, you can become so good at it that whatever rewards you seek become attainable.

I’ll say it again: I’m going to die one day. I don’t know if it’s next year or many decades from now or somewhere in between. What I do know is that expending my energies within the narrow, limiting, self-denying confines required by the traditional job is a complete waste of whatever existence I have at my disposal.

Aubrey has brought many incredible gifts of insight to my life, but chief of among them is this: you shouldn’t spend any significant amount of time doing something you don’t want to do. I owe so much of my evolution to that crucial realization.

I’m excited to be in business for myself. The nagging feeling that plagued me for so long, the feeling that I was somehow missing the point of life and wasting my time, is completely gone.

I’ve discovered a list of things that I absolutely love to do. I’m already good at some of them while others will require years of time to develop. That’s no problem – the love makes it easier to get through the rough spots. I’ve spent years aggressively growing myself to reach this point. I had no idea where I was heading.

Now I know. I can’t wait to be able to focus on what’s truly important, free from the distraction of minding someone else’s business.

A couple of months back, a Washington DC-based intellectual property attorney from a prominent national firm came for a tour. Let’s call this guy Rich. I was tapped to run the tour, but when one of the owners decided to come along, I spent the bulk of the morning opening doors and walking quietly alongside the conversation. I was extra quiet when the subject turned to the recording industry. Rich explained that he wasn’t terribly popular for representing the recording industry but that it was important work. He then trotted out the same tired old tripe suggesting that a decline in recording industry revenues was caused by piracy — a decline Richard assured us could be reversed if only young people were educated on the importance of respecting intellectual property.

This is Bullshit

I listened to all of this and swallowed so hard I bruised my own throat. First of all, as has been mentioned, piracy is murderous, ruthless work done by indefensible criminals. What these guys mean is bootlegging.

I failed to ask Rich if it were possible, just even the slightest bit possible, that recording industry revenues were on the way down because the record companies make over-priced garbage. I failed to mention that education is indeed necessary… for the luddite morons who ran these businesses into the ground in the first place. I failed to point out to Rich that if each pirated track really represented a lost sale, any miraculous absence of bootlegging would have to also transform the economy dramatically as to permit people the opportunity to drop $20,000 on a half-filled iPod Classic.

I failed to say any of it. Whaddya want from me? I’m not my own man for another few weeks yet.

Even so, the encounter was instructive. I learned that there still exist real, living, breathing people who believe this bullshit. Not to be ageist, but I suspect being over 30 years old has a lot do with this, though surely there are exceptions in either direction of that mark.

The recording industry has spent millions of dollars on technical and legal measures to prevent bootlegging. The pinnacle of that achievement? A multi-million anti-piracy measure that was defeated with a Sharpie and the most impressively tarnished image of any industry that doesn’t make guns or pollution. I’m talking out of my ass, but I expect that the number of people who partake in bootlegging has only grown since this crusade began. Talk about money well spent. Can you imagine where their business model would be if, instead of wasting their money fighting an unstoppable force, they’d instead took a good hard look at the way the wind was blowing and invested that cash in reinventing their business model in such a way that made bootlegging irrelevant?

The result would be a recording industry that neither you nor I could recognize.

Instead, the RIAA makes a habit of suing the very people to whom they’d like to sell their product while attempting to destroy any service or platform that challenges the traditional ways for people to discover music.

Unstoppable Force

Anywhere there exists a non-scarce encapsulation of value, that value will be reproduced and distributed outside the bounds of the author’s license or intent. Put another way, if your shit is digital and desired, your shit will be pirated. The question with piracy isn’t whether or not it will happen. The question, rather, is whether or not your digital property is valuable enough to be worth the trouble of pirating. Trouble, here, has a very flexible definition, depending upon how much stands between wanting to distribute and being able to distribute. This varies from platform to platform, from absurdly simple with digital music to decently pain in the ass with console games.

Why? There are two simple reasons. People want things and, as we know from economics, the capacity to produce is infinitely outstripped by the capacity to desire. Secondly, and most crucially, distribution is gratifying. People feel good sharing — that’s simple human nature. In many cases, too, distribution of something digital, something protected, requires solving someone else’s puzzle. The high that comes from accomplishing something intended to be impossible is well-known nerd crack.

Piracy is Always Possible

This recipe creates a world where the dreaded boogeyman of scary piracy will always exist. Any business model where a 100% lack of piracy is integral to success is doomed to failure. What to do about this truth is a difficult question — one beyond the scope of what I can tell you here.

What’s important to understand is that time spent fighting the unstoppable is almost always time wasted.

By definition, anti-piracy measures require an investment of development time that will never benefit your paying users. Who are you working for, if not your paying users?

You have a choice. You can allocate 500 hours to one of these options:

1. Building an incredible feature set that your customers love
2. Developing a new anti-piracy scheme that will be defeated in X weeks and may genuinely annoy your paying customers

Which do you choose? The exhausted Microsoft vs. Apple comparison is apt here. If you’re Microsoft, you roll out Windows Genuine Advantage and truly piss off anyone who ever has to reinstall Windows. If you’re Apple, you sell a five-pack license and let your customers buy on their honor. I’m sure there’s a decent set of folks who install Leopard on more than their purchased share of machines, but the Leopard family pack is ranked #201 in Amazon’s software sales and was an even better seller when Leopard was new. And you know what? Apple makes more money through the family pack than if they were dicks by using anti-piracy measures and only selling single-user licenses.

I’ve Got One Boss

And it’s not me. The boss is the customer. By definition, my customer doesn’t give a damn about the boogeyman. They want the very best features in a piece of software that does everything it possibly can not to annoy them. As far as I’m concerned, every minute I spend on anti-piracy measures for my apps is a minute I should have spent making something incredibly useful. I’m in this to make people happy with incredibly useful stuff. If can’t focus my time on that, there’s no point.

The only time I should worry about writing code related to users who haven’t paid me money is when their existence will affect users who have. If pirates adversely impact resources essential to your paying users’ happiness, by all means, write a bit of throttling code that gives their requests a lower priority.

You’ve Got a Decision to Make

Whether or not you spend time writing code that benefits you instead of your paying customers is a personal choice. I can’t tell you what you should do — that conversation is one you need to have with your collaborators and moneymen. The temptation is a strong one. I remember how angry I was when I discovered Tallymander being distributed by iPhone bootleggers for the first time.

Still: last week, I submitted my latest app, GlobeJot, for App Store review. GlobeJot’s source contains precisely 0 lines of copy protection code.

The choice is made easier for me by Apple’s inclusion of good-enough copy protection for iPhone OS apps. Even without that, though, I wouldn’t bother putting up much of a fight. I want to make money by creating honest relationships with paying customers who appreciate that I spend every last ounce of my energies making something they will love to use.

If that ideal one day ceases to be realistic, I’ll find somewhere else to put my productive ability.