I had grown up using mostly non-Apple products. My dad bought me a Timex Sinclair when I was six. I moved on to a Commodore 64, an Amiga 1000, and finally a Unix-based Sun 3/50 before I caught Mac fever in 1994. Two years later, I was working full-time at Apple as a software engineer at Apple.

When I signed on, Jobs was long gone, but his legacy was strong. Ten years after his departure from the company, bumpers in the parking lot remained plastered with the aspirational “The Journey is the Reward” proverbs that he had famously reiterated. Jobs made his mark, and the pursuit of excellence was alive and well inside Apple.

In late 1996, Apple announced that it would acquire Steve Jobs’s NeXT computing. Steve Jobs, in one role or another, was returning to Apple. I was overwhelmed, but excited. Although I had never worked for Steve Jobs, I felt that I had been working on his vision.

When I left Apple in 2002, it seemed that Jobs had won. He proved himself to critics by rescuing Apple from the throes of bankruptcy and restoring it to a company of huge successes. The iMac, iPod, and Mac OS X were all new testaments to his enduring legacy at Apple.

But he was just getting started. Still to come were not only the obvious iPhone and iPad, but dozens of less obvious successes ranging from the ever-improving Mac OS X, to the incredible Airport Express, to the fact that every damn thing Apple makes just works so damned well together.

Pixar Animation Studios is another of Jobs’s great successes. My three-year old, Henry, has lately been obsessed with everything Pixar. This includes “Cars,” which I have seen more times than I care to admit. It’s actually a pretty great film, and I’m fond of the romantic interlude where the protagonist Lightning McQueen is led on a carefree drive through the desert by his love interest, Sally. Their ride is set to an upbeat Randy Newman tune, which helps to pack an emotional punch in the scene.

Today I was driving in my own car, and heard an old Bob Dylan song that I realized the Randy Newman score reminds me of.  Steve Jobs is known to be a huge Bob Dylan fan, so it’s especially poignant that on the day of his retirement as CEO of Apple, I may have found myself listening to one of his favorite songs. Buckets of Rain also includes a concise proverb of its own, which serves as an appropriate comment on Jobs’s career:

“Life is sad, and life is a bust, all you can do is do what you must. You do what you must do, and you do it well.” — Bob Dylan, “Buckets of Rain”

Well said, Bob. Well done, Steve. For the rest of us: let us do what we must do, and do it well.

I asked him if he agreed with how they made their money. He replied in the negative — he’d just done the design. I told him we didn’t take on any projects that we couldn’t ethically stand behind.

And here I’ll quote him: “Must be nice.”

And that’s when I decided not to hire him.

Almost 15 years ago I was working my ass off at Apple as a junior engineer in the System 7 software updates team. I was trying to make a reputation in my new career, but also doing my part to make sure we shipped on time. In a historical sense, most what we built is hard to get excited about these days, but we were doing the exact same thing that Apple does today: iterating to give our faithful customers a reason to stay faithful.

In a group that was primarily oriented around fixing bugs, my colleagues and I were especially susceptible to a problem that plagues many developers: once you’re on the tail of a bug it can be hard to stop hunting until the issue is resolved. Some days we worked short hours. A hard-won victory at 4PM might be grounds for calling it an early day. But other times, stumbling onto a glimmer of hope with an impossible bug that “had to be fixed by next week” was cause for camping out until the wee hours of the morning.

One of these marathon bug-hunting sessions had a coworker and myself working until 2 in the morning, bleary eyed, but desperate for a solution. Usually I would recommend rest and resumption when it comes to this point, but we felt sure we were on the verge, and this was an important, difficult bug. We had a breakthrough, and spent another couple hours verifying a fix, testing it, and checking in the code. We went home exhausted but jubilant.

I collapsed at 5AM and slept until 11, conscious that the bug-busting marathon was not over. My boss, my boss’s boss, and for all I know, his boss’s boss were all aware of what we had done. It was a significant win for the team, but there was plenty more to do.

When I got into work after noon, my colleague was already there. He was talking, in the common area of our floor, with a humorless, long-time employee who worked in an administrative role with our team.

“Where have you been?” she asked contemptuously. “We need to ask you about the blah blah blah.” I’ve forgotten the specifics.

“Sorry, I was here late last night and only got in a few minutes ago,” I said.

“Must be nice,” she answered tersely. Her words stung. I was young, trying to prove myself, and had just returned to the fray after helping with an important victory. She had left at 5PM the previous night and had a long, restful night’s sleep. Or at least, that’s what I assumed she did.

What irked me most about her “must be nice” comment was how profoundly void of empathy it seemed to me. I hated her for years because of this. In part because of her, I have since been extremely sensitive to these pithy, jealous expressions: they jump out like smarmy little diamonds. But when words like these occasionally get lobbed at me, I am not nearly as hurt as I once was. I tap into my own empathy reserves, imagine what a crappy life they me struggling with, and try to wish the best for them.

It’s not so nice to be a person who says must be nice.

I love the idea of highlighting things that others have written, but since I don’t have a convenient repository of these items, and haven’t got time to scour my mind for suitable candidates, I’m sticking to what I know best. Presented here with a brief synopsis:

• Adiós a las Computadoras Dell. On the eve of Apple’s transition to Intel processors, I speculate that the end is nigh for Dell.
• Magical Code. Based on my experience working at very low levels inside Apple, and on my own high level stuff, I dispel the notion that any code is so magical that you can’t understand it.
• Five Things I May or May Not Know. Particularly meaningful for folks who are grappling with the idea that their full-time work is not for them, and are toying with the idea of branching out on their own.
• The Road Less Traveled. The story of my transition from a full-time Apple engineer to a self-bootstrapped software business owner.
• Forget the Shortest Path. Wisdom inspired by lessons in sailing. Sometimes moving directly at your objective is not the most pragmatic way of reaching it.
• It Should Be Free. My reaction to the expectation among some customers that things should be free. I dig into the true cost of “free” things.
• Getting Pretty Lonely. My rant against the GPL open source license.
• Elements of Twitter Style. My fairly recent prescription for getting the most out of Twitter, while annoying the fewest.

Thanks, as always, for your attention to my blog and my writing.

I was lucky to end up as a Quality Assurance tester inside a software development group at Apple. I worked for the Software Update team, which was essentially responsible for diagnosing, evaluating, fixing, and shipping bug fixes for anything in the System 7.5.x era software that Apple was building at the time.

I was so bold back then that I told my bosses, and my bosses bosses, and my peers, and anybody who would listen that I wanted to be a programmer. I wanted to write Mac software. No, I wanted to write the Mac!

That dream came true on May 12, 1996, when I joined Apple as Software Engineer I in the System Updates team for Mac OS Engineering. I immediately went to work, fixing bugs here and there as fast as I could. I took copious notes, in an effort to assure my bosses that I was the right person for the job. How did I spend my time over the past 5 minutes? I could happily elaborate.

I was so nervous about my performance, so worried that somebody might notice I was a fraud, that I didn’t ask for help as much as I should have. When somebody assigned me a problem, I scraped the walls of hell to find the answers, lest it be revealed that I wasn’t quite as smart as I might have seemed.

All the bugs in our group were difficult. One day I was assigned a particularly vexing one. I had shown a knack for tracking down tricky issues, but this one stymied me. I hammered away at the bug but I couldn’t figure out the cause. I couldn’t even think of where to go next. I was petrified. This was it, they would learn about my incompetence and put me out to pasture. I decided to take a walk.

I clearly remember that balmy summer day in Cupertino. I was filled with dread. I walked from Apple’s Infinite Loop headquarters, across Highway 280 on De Anza boulevard, towards the expansive suburban doldrums of Sunnyvale.

My pre-hire boldness had abandoned me. “Maybe I should quit,” I thought to myself. “That would be a stoic way of getting out of this mess.” It sounds so dramatic in retrospect, but I was so sure of my failure, it seemed like an obvious move at the time. I talked myself through the facts of the bug in question, and simply could not think of a solution. I couldn’t think of a part of a solution. I couldn’t even think of a step in the direction of a solution.

I walked for an hour or more, and then returned “home” to my office at Infinite Loop. I sat at my desk and stared into the monitor, hoping against hope for some inspiration. My friend and coworker, Darren Litzinger, stopped by my office.

“What are you working on?” he asked.

“I have a terrible bug, and I can’t figure it out.” The thought of asking for help didn’t even cross my mind. But fortunately, my frustration spoke on my behalf.

Darren sat down in my guest chair and adopted an excited look. “Well, what do you know about the bug?” He was here to help. I hadn’t even asked for it, yet here he was. I could have asked for it at any time, and I didn’t even realize it.

Talking through the bug with Darren, he asked me to perform particular tests at the computer. I realized that we had completely different approaches to problem solving. It wasn’t that his were right or that mine were wrong, they were just different. As it turned out, his technique saved the day and we got to the bottom of the issue within a couple hours.

As I moped along De Anza Boulevard that afternoon, I thought that I might not be cut out for software engineering in general, let alone at a world-class company like Apple. After I retreated back to my office and got a surge of help from a trusted colleague, I realized that I was perfectly qualified for the job. Especially if I could ask for help every once in a while.

I was lucky to join one of the most cavalier and competent teams in the company: the Mac OS system integration team. In a nutshell, we were in charge of the Mac OS System File, “System Enabler,” and other crucial bits that made your Mac a Mac. Whoo-hoo! Power! We made or broke your Mac experience, hopefully making more than breaking. I took my new job seriously and stepped carefully with every change. It felt great, and I cherished every contribution I made.

Later, I moved to the Mac OS X team and did similar work on the infrastructure of Mac OS X. In particular, with how it deals with older applications that rely on the “Carbon” framework. After years of using a custom Mac-only environment called MPW, I was using standard UNIX tools and building UNIX libraries. This felt awesome! I had grown up using an Amiga, then switched to Sun OS, where I spent a lot of time getting familiar with UNIX. There I was, and Apple decides to put the best UI in the world on top of Unix. I was in heaven.

While I was at Apple I saw a lot of failure. I saw the Newton fail. I saw Pippin fail. I saw PowerTalk fail. I saw Cyberdog fail. I saw Apple desperate to sell even a few hundred thousand Macs in a quarter. I saw the press lambast us and declare us dead. “Beleaguered” became an unfortunately common word in our office life.

But I kept looking around me, and I saw nothing but signs of success. I marveled at QuickTime, speech recognition, networking technologies like ZeroConf (Bonjour), and other things that have never seen the light of day. This company is awesome! I want to work here! They’re going to change the world!

Of course, they already had changed the world with the Apple II and the Macintosh, but as a young 20 year old, I was anticipating future growth. It was a bad time for Apple: competitors and the press were declaring our obsolescence. Michael Dell said we should give the money back to the shareholders and close the company. We persisted on a wing and a prayer, driven by Steve Jobs’s admonition that we could beat Dell. I believed in that mission, and I believe in it still.

In 2005, I wrote boldly about the end of Dell, and I have to confess I was a little over-ambitious. I could see a path where Apple would take Dell down faster than they have. I was wrong. Dell is still a strong  company. But that will change soon.

I joined Apple because they were threatening to change the world. I stayed on at Apple because they were changing the world. And I remain loyal to that company because, in spite of my absence, they have changed the world. In more ways than I can imagine, they’re inventing the future. And I’m along for the ride.

Dell is not changing the world, Microsoft is not changing the world. Hewlett-Packard is not changing the world.

Apple is changing the world, and damn it feels good to be part-Apple today.

I got to know Buzz online, through his blog and through occasional chat sessions on IRC. As it happens, I moved away from San Francisco just before I got to know a number of people online who I wanted to meet there. But since I visit often, it came as no surprise that I ran into Buzz one day at a cafe in San Francisco’s Mission District. I was sitting with my coffee when Buzz sat down a few chairs away. I recognized his resemblance to an online photo and introduced myself. He snapped this photo of me. Afterwards, we walked down to Mission Street, caught a large street protest, and then I took him to my favorite thrift store.

I was relieved that Buzz didn’t hold any personal grudges against me. After my public critique of his decision to bow out of an interview with Cocoa Radio, he would have been entitled to. He was feeling the pressure of forces inside Apple. I was feeling feisty, probably partly because I had felt similar pressures as he was then responding to. My provocative post was sassy enough to warrant a vendetta, but Buzz showed no signs of holding one. I was grateful for that.

A lot of the themes in Buzz’s blog entry hold true for me as well. The desire to work for such a great company contrast with the lure of indie-freedom. Most people think I’m being dramatic when I say that I have regular dreams about my time at Apple, but it’s true. I have at least one dream per month. Surreal dreams about fantastic Apple office buildings, where my old co-workers behave somewhat more like characters from Twin Peaks. I’m always pleased in my dreams to be back in the comfort of my Apple life. These have become a regular staple in my subconscious life. A replacement for the “showing up to school naked” dreams of earlier years. That company put a spell on me, and it’s not likely to wear off any time soon.

I’m sure it’s true for Buzz as well. As he pulls away from the safety and comfort of that great Cupertino establishment, he isn’t leaving Apple behind. He’s taking a little piece of it with him, to share with the rest of the world. Good news for the world.

I stumbled upon it today and found this choice bit of commentary on MarsEdit itself. I find myself frequently responding to the concerns of users by saying “Yes, I agree! I want to fix that!” Well, this isn’t proof that I really mean it, but it’s pretty good evidence:

MarsEdit. MarsEdit is, like NetNewsWire, extremely helpful to my daily routines. I tend to write a lot of blog entries, so I keep MarsEdit open even if only to capture vaguely bloggable ideas. In fact, this entry has sat in MarsEdit for a few days [UPDATE: Almost a year :) ] as I accumulate enough applications and opinions to make it worth posting.

My biggest complaint about MarsEdit is its lack of a search facility. This has everything to do with this “capturing ideas” behavior of mine. At any given moment I have the last several of my published blog entries as well as a number of drafts stored in the application. Right now there are 31 items in the Drafts folders. That’s right, 31 items that you don’t have to read (yet!). [UPDATE. Now it's 52]

When I want to resume work on any of those drafts, it’s infuriating to not be able to easily pop it open by searching on a unique keyword. I went so far as to write an AppleScript aimed at performing the search for me, but alas MarsEdit’s scripting interface doesn’t allow access to the text of drafts, either.

MarsEdit needs a search field just like its cousin NetNewsWire has.

So, believe me! I care. I want this thing to rock, and I’m in a very good position to make sure that happens.

Oh and incidentally, I wonder sometimes if people will suspect me of “carpetbagging” this target audience. I mean, here I am I just pulling into town with a truck full of shiny new blog editor. But I have been interested in writing a blog editing application for a long time! In fact, I’ve even got some stale abandoned projects around here somewhere. In 2003 or so I noticed Michael McCracken’s open-source Blapp and seriously considered diving in. I thought with support for a few more blog systems it could really kick ass. You know, like MarsEdit.

A few years later I was deep into WordPress and again considered writing my own custom client. This time I was using MarsEdit, but hoping for even better integration with WordPress. Luckily, I never started that project. Also luckily, I am going to be able to finish it.

The best part of the video? In the midst of all this enlightened modern living, the video shows a man scribbling away on his Newton while talking on the phone. A pay phone! If only they could somehow combine those two devices! I also like the knowing look and raised eyebrows one worker gives to another just before she “beams” him a message. A subtle suggestion that Newton might actually get you laid.

I never used a Newton much, although I occasionally had my hands on one at work for some debugging purpose. Some of the design considerations really pop out, like the fact that the Newton was almost entirely “soft button” based, much like its nascent offspring. The soft QWERTY keyboard is even reminiscent of the iPhone’s, except that with the Newton it was only intended to be used when the handwriting recognition made a mistake.

Which it did. A lot. Many people consider the failure of adequate recognition on the Newton, and the basically functional compromise of Palm’s “Grafitti” to have been the death blow for the gadget. Amid all the happy music and smiling people, you can tell the issue was weighing heavy on Apple’s mind, too. Halfway through the video the topic changes to “handwriting tips” and more or less stays on the subject for the rest of the promo.

If Apple presents iPhone along with a promotional video that is half devoted to teaching users how to workaround the device’s bugs, then we’ll know it’s doomed.

The same mental bug appears at more depressing moments. We might spend a decade feeling essentially the same about our health and vitality, until we look into the mirror one groggy morning and see a particularly aged face staring back at us. Before we know it, we’re yesterday’s news. So it goes with pop music, our bodies, and with the computers we use every day. Having fun yet?

While I was working at Apple, I had the privilege of contributing to the transition from Mac OS 9 to Mac OS X, as a member of the Core Services group. At that time, there was no doubt in anybody’s mind that Mac OS X was new. It was so new in fact, that for a long time nobody took it seriously. As pre-10.0 developer previews rolled off the line, Mac OS 9 loyalists insisted that it would never supplant their favorite operating system. Mac OS X was just some newfangled thingamajig that the crazy kids were playing with.

Then lots of years passed and, lo and behold, almost nobody uses Mac OS 9 anymore. I was using Spotlight to try to track down a copy of Resorcerer, when I stumbled upon this old folder full of aliases, in an old backup directory from a home computer when I was still on Mac OS 9:

What is this list of sundry items? Well it’s the folder of aliases I put in my Mac OS 9 “Apple Menu items” folder. The quick-access list of items that I could easily access at any time. Now, I’m not sure how accurate this list is as a reflection of my everyday application usage. At this time I was probably using Nitin Ganatra’s excellent Malph utility for most of the same purposes. I’m also not sure how much different my work machine’s list would have been. This was my personal machine at home, which I obviously used to some extent for work development. What strikes me today, looking back, is that almost every one of those applications has been supplanted by something else. They were all very appropriate to my computer life only 5 or 6 years ago, but now many of them are ancient relics.

Let’s go through each of them and figure out what used them for then, and what I use now to achieve the same goals.

BBEdit. To be honest I’ve never used BBEdit as my 100% full-time editor, but it’s almost always “been around” in one form or another for something important. At this time, I probably was using MPW for most of my text-editing needs, but would occasionally open up BBEdit to do some particularly advanced search & replace, or to sort by columns or something. I still use BBEdit largely in this capacity, though one of the major ways I use it these days is as a file comparison tool (I find it more reliably with strange line endings than Apple’s FileMerge application).

CyberStudio. I can’t remember whether this application was called “GoLive” at the time, but I’m pretty sure it was. Adobe had come to Apple for one of our irregular (at the time) beer bashes and offered us free copies of the app. I used it to design my personal web page for some time. Eventually I switched to Macromedia Dreamweaver, which I used for a few more years, before finally relying mostly on manual CSS editing.

Fetch. For a long time, if you wanted to use FTP from a Mac, there were really only two choices: Fetch or Anarchie (now Interarchy). I dabbled in both but mostly found myself using Fetch for the rare occasion on which I needed to push files. These days, I tend to use Fugu for uploading to my SSH enabled servers. It’s got a lot of rough edges, but it’s free and basically functional. If I needed to do more file transferring, I’d probably use Transmit, like everybody else.

Internet Explorer. I remember sitting in the lab at Apple, as a QA Engineer in 1996 or so. Everybody was still using Netscape Navigator, but this new Internet Explorer was grabbing our attention. My, it was a nice upgrade at the time. IE came with us to Mac OS X in the early days, but of course Safari eventually came along and proved an easily superior alternative to the aging IE.

Microsoft Word. Like everybody else in the world, I had to keep a copy of this app around just to be able to reply to the emails from marketing or whatnot, which were inevitably in Word format. These days the popularity of PDF has gone a long way towards eliminating the need to use Word as a generic document format. I do think Word can be a pretty nice word processor, but when I wrote the thesis for my BA in Music in 2005, I used Apple’s Pages with a good deal of satisfaction. It’s what I would use again if I had to do any substantial amount of non-blog writing at this point.

MPW Shell. At this time, most of the Mac development world was using CodeWarrior for day-to-day development purposes, but in my group at Apple everything was still tightly bound to MPW. It made up my editor and source control management (projector – yuck!), with MacsBug serving as the debugger. These days of course, it’s all Xcode and GDB. I miss some things about MPW, especially the highly (and easily, compared with Xcode) customizable menus. And I miss some things about MacsBug. But on the whole, Mac OS X in 2006 provides a much better environment for development than MPW on Mac OS 9 did.

NiftyTelnet. When I first worked at Apple in 1994, I was bit of a freak to my coworkers. In those pre-OSX days it was rather uncommon for anybody at Apple outside of the A/UX group to be interested in telnetting to a UNIX machine. But I had just come from UC Santa Cruz, and was tied up in a certain amount of command line computing lifestyle there. For instance, I wanted to be able to check my email. I’m not sure what I used in those earliest days. Possibly ZTerm? All I know is as life went on I still had the occasional need to connect back to my school’s alumni server, and eventually it became NiftyTelnet with its SSH support that best served the purpose. Of course on Mac OS X I still do quite a bit of ssh connections, but it’s almost always through the standard command-line tool that ships with the operating system.

ObiWan. Oh, ObiWan, how I adored you! This utility was like my third arm during those years. It served as a comprehensive, instantaneous reference for the Mac OS API. The touch of a hotkey would present a floating window. Type the name of the API to see the prototype instantly. Another hotkey pasted the prototype directly into your code. Of course, we get more or less comparable behavior for free nowadays in Xcode, but I’m amused to see that ObiWan was in fact ported to OS X, renamed WanObi, and is available for download through the Stairways FTP Server.

Outlook Express. I don’t really remember using Outlook Express, but this snapshot must have caught me at least dabbling with it. I was interviewed by Tim Gaden about my mail habits, and neglected to mention this in my history. All I know is that I use Mail now and have consistently for the past 6 years or so. It’s not perfect but it gets closer than anything else I’ve tried.

Pro Tools Free. Digidesign made the incredibly cool marketing move of giving away a free version of their venerable recording software. I used it for my hobby of songwriting and (very!) amateur recording. The marketing worked: I was hooked on Pro Tools and convinced that I would hate using anything else. Unfortunately by the time I wanted to upgrade to something more sophisticated, Pro Tools had not finished their OS X support, but MOTU had. I bought a MOTU 828 and switched to their free version of Digital Performer, called AudioDesk. These days I’m just as likely to pop open GarageBand if I feel like playing around with some recording.

Radar. Radar is a private Apple application for interacting with the internal bug database. You know, I really had a love-hate relationship with that application, but I would love to be able to use it again, instead of the frustratingly limited web-based version that we’re forced to use as company outsiders. It was a lot better than many of the open source and commercial options I have been subjected to by the various projects I’ve worked on over the past few years. For my personal projects I don’t use anything more formal than a series of conventionally named text files, but I keep meaning to remedy that.

ResEdit and Resorcerer. These were the two options for editing resource files, which was an essential part of any Mac development effort. These days I still use Resorcerer from time to time because I’m unlucky enough to have legacy projects which require resource fine-tuning from time to time. But for the most part, their use has been replaced by Interface Builder on OS X, which lets you lay out interfaces in a much more intuitive way. The feature I miss most from the resource-editing days is the ability to store arbitrary hex data, while allowing for extensible editing via template definitions. Interface Builder is pretty frustrating when it comes to storing anything non-standard.

SoundJam. Those of you who have been around a while remember that SoundJam was one of the early MP3 Playback offerings on the Mac. It was the one I ended up using, and I still use it today, it having been purchased, rebranded, and massively expanded on by Apple as the iTunes we know, love, and hate today.

I’m sure there were lots of other applications that played a role in my day-to-day work at the time, but these just happened to be the ones that were in my Apple menu. They must have been important to me then, and I’m impressed to see that very few of them are very important to me today. I wonder how the application landscape of my computer will change over the next 5 years.

Last year, Gus Mueller of Flying Meat Software wrote a powerful blog entry describing the 1068 days that elapsed between his setting out to be a full-time indie software developer, and achieving that goal.

Paul Kafasis recently redirected my attention to that post, and commented that it would be interesting to hear more stories of the much-varied road to indie-dom. He has posted his (and the other two founders of Rogue Amoeba) very fun story: The Full-Time Gap.

I’m impressed and inspired to read any such stories, especially when they describe the troubles that successful entrepreneurs have struggled through. When we look at the examples of successful companies in any industry, it can be hard to imagine that they once floundered, made stupid decisions, had an ugly web site, couldn’t make any money, etc. There’s hope for us all!

At first I thought it inappropriate for me to participate in this conversation, because by my own standards I’m far from having reached any kind of ISV (independent software vendor) success. But then I consider the fact that I haven’t had a “real job” for four years, yet I have roughly the same amount of money in the bank and a new college degree under my belt. Not too shabby, after all. I hope my story will be inspirational in its own way, different from Gus or Paul, but another example of how “this can work.” I’ll adopt Gus’s and Paul’s habit of occasionally highlighting some salient (I hope!) point of wisdom. These lessons, collected from all such posts, may help you maintain optimism and courage when pursuing your own dream.

Sink, Swim, or Float

When discussing the indie dream much fuss is made about “making the leap.” This idiom can be applied to many risk-taking situations, but in this context it usually refers to that fateful day when an individual decides to stop receiving a steady paycheck, in favor of some pursuit which probably offers less certain financial rewards.

Your familiarity with the phrase is inextricably linked with another well-worn utterance: “don’t quit your day job.” This phrase probably started as a cautious piece of well-meaning advice, but has evolved into a nasty weapon, used by terminally unhappy people to assassinate the dreams of those who aspire to something different.

Lesson: Don’t let other people dictate your dreams!

On July 8, 2002, I announced to my colleagues that I would be “quitting my day job”:

Now, at most companies this move would have invited howls of “don’t quit your day job, sucker!” But remember, Apple Thinks Different. I cherish the replies I received over the next few days. All of them extremely positive and encouraging. No dream assassins! And it wasn’t even because they were happy to see me go. (I don’t think!) Some excerpts, edited for anonymity:

Lesson: Find encouragement early and hold on to it. Never stop repeating it to yourself. You are entitled to pursue this dream.

But before we fly away on a rainbow cloud of optimism, let’s put things into perspective. People say “don’t quit your day job” because honestly, most of us need a day job. Here we get to the “floating” alternative to sink or swim. I was leaving a well-paid job to go to school – a negative paying job. It would have been foolish for me to do this without money in the bank. Because of my frugal lifestyle (no Porsche!) and a belief in my company’s stock that was finally beginning to bear fruit, I was decked out in safety gear when I made the leap. I would not be making money, so I needed a life jacket. I needed to float.

My experience demonstrates the awe-inspiring power of fear. Even with enough money to comfortably survive a couple years back in school, and a buffer period for getting a job again afterwards, I was still scared out of my mind to leave the comfort and security of my career. I think it’s illustrative of a defect in thinking that keeps many of us from taking the risks we should. Instead of looking at the real risk, which was that I might use up all my savings and have to start saving from scratch, I let my mind enumerate all the possible risks. Nobody would hire somebody with a weird gap in their resume. I’d run out of money and have to move in with my parents. I’d never again have an opportunity like Apple. I’d be irrevocably labeled a failure at life.

Come on! Life’s unfair, but it’s not that unfair. Wherever you are right now, whatever your position of comfort and satisfaction, chances are excellent that you’ll be able to return to that position after failing to pursue your dream. And remember, that’s the worst case scenario.

Lesson: Take risks. Don’t take foolish risks. Easier said than done (or not done), but important.

Catching an Income

I spent my first year back in school slowly draining my savings. Don’t worry, when I say slowly I mean really slowly. I didn’t even try to live too cheaply, but I had kept some habits that made me a pretty slow consumer of funds. Eat burritos, watch broadcast TV, buy thrift-store clothes, etc. By not buying a Porsche, or any other expensive car, I had easily come to own my Ford Escort outright. No monthly payments. No debt. Cheap (for San Francisco) rent. This was doable! I haven’t added up the math carefully, but I think it’s reasonable to estimate that for the first year I used up maybe $15,000 in savings, and that includes my university costs. By not driving to work every day, my gas bill went to nil. I avoided the rich lunches out that accompanied work, and abandoned all of those gadget-buying habits that mainly serve to soothe the confusion that comes with having a lot of income and nothing to spend it on.

Lesson: Make your risk count. Don’t spend your savings at the same rate you spend your income. Adjust your lifestyle so that your savings far outweigh your costs.

I would be lying if I said I wasn’t afraid, even with the slow leak in my bank account. It never feels good to lose money. So I started to look out for a job. I thought for sure it would be something student-like, since I figured my schedule wouldn’t accommodate anything in the tech field. I went to the student employment office and tried to picture myself working in the library or as a departmental assistant. $9/hour was looking pretty good.

Then I noticed a craigslist ad for a company in search of Mac developer. It was the beginning of summer, so I could afford to work full-time for at least a few months. What do you know, this position was a short-term porting job from OS 9 to Carbon on OS X. The requirements sounded like they were lifted directly from my resume, so I contacted them and almost immediately got to work on my first contract.

Lesson: The adage about making your own luck is true. If you don’t keep your ears open for opportunity, you can’t blame anybody but yourself for your failures. Luck is lurking everywhere: in the obvious places and where you’d least expect it.

Over the summer I earned enough money to replace the lost funds from the past year, and go a long way towards subsidizing the year to come. I had been ostensibly running “Red Sweater Software” as a shareware company for a few years, but hadn’t really made enough income to justify a bank account. I asked the company to make the checks payable to the company name, and opened a new business account. This would be the first year that I could easily and honestly report significant income for my business. I bought a new G5 and deducted it from that year’s taxes.

It’s cheesy, but just having a bunch of cash in the bank under a business name made me suddenly feel like a business. It immediately broke down a mental block I had previously suffered, viewing businesses as something other people, brave people, took part in. The manager at Bank of America wished me good luck and handed me a company checkbook. I could be a business, after all!

Lesson: There’s nothing magical about businesses. They’re just people who choose to earn their money directly. If you can convince somebody to pay you, you can be a business, too.

Aim Higher

As I proceeded to spend another two years earning my degree in music, I just sort of picked up other contracts here and there. As it turns out, lots of companies are very flexible when it comes to hiring Mac programmers. After all, they don’t have a lot of talent to choose from. You’re coming in to their company to fill a gaping void. The fact that you’ll do it in your spare hours over the course of a couple months often doesn’t matter to them. Once I realized that it was OK for me to be a consultant and a student at the same time, I cautiously accepted new contracts. It was difficult at a few points to perform professionally in both work and school, but by declining several otherwise appealing contracts, I was able to keep the workload small enough that I could comfortably do both.

Lo and behold, I had quit my job to pursue one dream (education in music), and had inadvertently stumbled into satisfying a latent dream: owning my own business. Red Sweater Software was a profitable enterprise, even while in school! I joked with my friends at Apple that I was making only about half what I earned at Apple, but that I was working about a quarter of the hours. Not a bad tradeoff.

Lesson: Some dreams will be realized by accident or surprise.

After I graduated and received my degree in May of 2005, I realized I was at a crossroads. Just as younger students are suddenly faced with the question “what do I want to do with my life,” I had to decide where to focus my energies. I had enjoyed the single-mindedness of school. There was always something important to focus on. Nobody could call me a failure because I was working towards something. Now I had to decide whether success and happiness lie in going back to a full-time job, maintaining the new status quo (consulting), or in pursuing something completely different.

It so happens that around this time I moved from San Francisco to Boston. This pretty much wiped the option of going back to Apple off of my list. I could interview in Boston but I didn’t have a fiery desire to work anywhere but Apple. I decided that the status quo would suffice, especially since I had gained some long-term clients who were happy to retain my services even after I moved. Having this “portable job” proved very comforting in making the huge transition to a new city on the other side of the country.

In Boston, I discovered there is just as much demand for Mac consulting as in San Francisco. That is to say: not much. But if you keep your eyes peeled, you find it. And the lack of competition means that often you’ll be the first person to contact a prospective client. Make a good impression and odds are you’ve got another gig. So I have spent the past year or so continuing with consulting work and enjoying the relatively laid back lifestyle it affords. I sleep in. I start and stop the work clock at my own whim. I write great software for great companies.

Lesson: Consulting makes an excellent back-up plan. You’ve always got a job if you need it, and your destiny is very much in your own hands.

But I’ve got another dream. I want to be a great company. In May of this year I decided that my ambitions of selling software directly to customers were not being adequately served. They had been put indefinitely on the back burner in favor of serving more and more paying clients. But there’s no reason that Red Sweater Software can’t be one of the great companies that is served by my talent.

But in spite of the relatively small number of Mac gigs in the world, my schedule was full! I was already turning away work because I didn’t have the time. How was I going to make time for Red Sweater Software? The decision I had to make is especially difficult for anybody venturing “out on their own.” The survival instinct is so great that a paying job becomes very difficult to turn down. In order to make time for my dream, I had to trade in paying jobs for time that could be spent on developing, testing and marketing my own software.

Lesson: It costs money to start a business, including the money you could be getting paid elsewhere. Balance the pursuit of money with the pursuit of your dream. They’re related, but not the same.

FlexTime was the first product to come out of this risky (but not foolishly so!) plan. After months of work the product went on sale last month, for $18.95. In spite of being satisfying to me, and receiving the praise of some very respectable bloggers and users, FlexTime is so far a “failure.” Why? Because sales are in the low hundreds of dollars. Without further development, I cannot expect to recoup my investment, let alone expand the company. Fred Anderson or another financially savvy person would deem it a failure. But it’s my failure! Mine, mine, mine! It’s mine to tweak and enhance. Without the determination to at least fail, I’d never have a chance to succeed. And the stories of more successful companies like Flying Meat and Rogue Amoeba assure me that it’s OK to fail. As long as I learn from my failures.

Lesson: Don’t be afraid to fail! Failure is your only means of testing for fact. And without facts, you have nothing to base your business on.

See, I sort of anticipated from the beginning that FlexTime would not be a huge success. I mean, I really hoped I was wrong, and braced myself to be pleasantly surprised. But I was not alarmed to learn that millions of users would not be beating a path to organize the “linear, timed activities” of their lives.

But FlexTime was a success in a way that I very much intended. It’s a proof of concept. Not of technological functionality, but of ambitious determination. FlexTime is proof that I can embrace a software development strategy that starts with a product vision and ends in a sellable product. My previous products were not good proofs of this because they sort of evolved resistantly out of personal projects. They didn’t start out with customers in mind. Though I’ve done my best to retrofit them as customer-ready products, they were designed almost exclusively to meet my needs. It’s a coincidence that others find them suitable for theirs.

FlexTime was developed from day one with the customer’s interests in mind, and as a complete product that serves a specific purpose, I’m proud of the result. Now that I’ve proven the concept, my success is all but assured. The machinery is in place, now I just keep turning the crank until something irresistible comes out. Until you know your machinery works, it’s almost a waste of time to set your sights as high as a successful product. Get your first product out of the way as soon as possible, and learn from your mistakes.

Lesson: Pick a small project, design it from the ground-up with customers in mind, and work tirelessly to complete the vision. Then you’ll know your machinery works.

My first success might be a revision to FlexTime (or FastScripts, or Clarion), or it might be something completely new. It might take a year or it might take five years (please, no!), but let me repeat: my success is guaranteed. And yours is too, if you choose this dream and pursue it diligently.

Bring On the Stories

Have you taken the road less traveled? Halfway down it, or just thinking about setting out? Let’s hear your stories. Your successes and your failures. Because the failures are successes, too.

Thanks to Gus for starting this topic and to Paul for reviving it. I’m looking forward to reading more stories along these lines over the coming weeks.

Update: Stories I have noticed being written since this was posted, either inspired by or of a very similar style as Paul’s, Gus’s, and mine:

• Michael Dupuis – Advenio
• Geoff Schmit – Sugar Maple Software