Last week marked the 30th anniversary of Macintosh, the adorable little machine that coined the phrase “Please insert Disk 1. Please insert Disk 2. Please insert Disk 1.” While they didn’t always have the cachet and widespread adoption of today’s Macs, these little machines touched my life in small ways in each of the last 30 years.

1984: Arrival

I was seven years old when the original Macintosh arrived in our house. I liked it right away because while my dad was distracted setting it up and swapping disks endlessly, the Apple ][e sitting next to it was completely freed up for my gaming needs.

With no games to play on the Mac, I remained skeptical until my dad showed me MacPaint. He drew (possibly from a tutorial) a hot dog with spray-painted relish (see crude reconstruction). MacPaint (or, as I called it, “MacPaint by Bill Atkinson”) became my first Mac game. I’d set up battle simulations and stage elaborate strikes (playing both sides) using the spray can as a gun and the polygon tool to build defenses.

1985: Desktop Publishing

By 1985, our house contained an unheard-of-at-the-time five computers; we had an Apple //+, Apple ][e, Apple ][c, a Macintosh, and a Kaypro. The (supposed) reason for such a plethora of technology was that my father was a professor of printing. He had invented a way to connect an Apple ][ to a traditional phototypesetter and was now exploring what Macintosh could do for publishing and printing.

In 1985, the LaserWriter and Aldus PageMaker came along and suddenly everybody saw what Macintosh could do for publishing and printing. There was a lot of desktop publishing going on at our house that year, and I remember running my fingertips over the warm paper coming out of our LaserWriter and feeling the embossed toner. The 300dpi output seemed impossibly crisp.

1986: //GS vs. Mac Plus

In 1986, our disk swapping days came to an end with the arrival of our Mac Plus. We also somehow acquired an Apple //GS (Woz Limited Edition). My curiosity with the Mac continued, but my devotion to the platform with all my games endured. The //GS tutorial software seemed at the time to do everything that the Mac could do, but in glorious color. Of course, like many, I just used the GS as a glorified Apple //c and never booted into GS/OS. I wasn’t even aware of what it was until years later.

1987: Mac II

1987 brought us the workhorse Macintosh II that would be the centerpiece of the “computer room” in the new house we moved into that year. It would remain my dad’s primary machine for several years thanks to its expandability and dad’s tendency to stretch the limits of how many devices could be on a SCSI chain. Side note: one time, he and an associate decided to see what happened if you double-terminated a SCSI chain; turns out, burning.

The Mac II brought us so much joy, like the time I installed an extension (SoundMaster?) to customize alert sounds and it completely jacked the computer, losing a few hundred pages of edits to my dad’s book in the process.

It was around this time that a PC appeared in our house, though it was mostly ignored except when I used it to play games.

1988: Scanner

Our desktop publishing setup reached professional levels in 1988 with the arrival of the Apple Scanner, though I have no idea what we used it for since Photoshop was still two years out.

1989: SimCity and Cardversham

I remember when my dad handed me a copy of SimCity, he told me that it was so detailed and accurate that real life city planners were using it. It didn’t sound particularly fun, but once I got started, I don’t think I stopped until Klepland had reached the pinnacle of metropolitan success only to be consumed by fire since the mayor didn’t believe in building fire departments until a fire broke out. My other draconian mayoral extreme — high crime areas are resolved through demolition, not through additional police expenses.

I also worked with my dad and my best friend Paul to make a series of hockey trading cards for our neighborhood basement hockey league. Cardversham released several series over the next few years, even including a price guide and rare (intentional) error cards. At times we used some of the high end Macs and super expensive printers at my dad’s lab at RIT to make the cards. Going to work with my dad was always a good way to preview the technology everybody else would have in a few years.

1990: Photoshop / LC

Finally! A use for the scanner! Let’s scan the teacher’s picture from the yearbook, give her a third eye and a unibrow, then bring it to school and claim some other kid did it! Sorry, Alan, but appreciate you taking the fall.

Also notable this year: Spanish teacher asked each kid to bring in a box of tissues because, you know, budget cuts. Dad and I designed a custom tissue label in Photoshop and PageMaker with the phrase “A healthy nasal organ is a tribute to Mrs. Horgan”

In 1990, I got my first Mac that was mine alone. I remember that the day it was due to arrive I was at a Model UN conference and found it very hard to concentrate knowing that a pizza box shaped Mac LC was home waiting for me. Like virtually every other Mac LC owner, I named her “Elsie”. Then I spent hours just planning my folder structure (“School”, “Games”, etc.), attempting to get it to mirror the way my brain was organized.

My LC also had the optional Apple // emulator card because, of course, I wanted to keep playing all my classic games. I don’t recall ever using it.

1991: HyperCard

HyperCard likely came into my life around 1991. I remember exploring the wealth of stacks that you could get on CD-ROMs. I’m not sure exactly when I moved from being a user to developing my own stacks, but I came to view HyperCard as the only development environment one would ever need. I figured that if you could simply get the cards to switch fast enough, you could do videogame animation in HyperCard.

Notable stacks I remember creating: An interactive driving game using real streets from my neighborhood (unfinished), a dream journal, and various stacks that would play sounds when you clicked things.

1992: MacGames Digest

My dad used to take me to MacWorld in Boston each summer, where I would hear him give the pitch for the lab he was setting up at RIT and then get annoyed when people would say to me, “Are you learning about computers, little boy?” In 1992, or maybe 1991, but you’re not going to look it up so let’s just say 1992, I saw a demo of Spaceship Warlock at MacWorld. I only got to see one brief part of the game — you go into some sort of bar in space and you can order any drink. The robot bartender then mixes something that looks just like what you ask for! The guy giving the demo even took requests from the audience. For some reason, I was fascinated that you could type in “martini” and get something in a martini glass. Type in “beer” and get a bottle of beer. I had to have this game.

Coincidentally, I was getting into USENET at the time and saw a post from a guy named Dean Davis who was starting a new Mac Gaming magazine called MacGames Digest. I volunteered to be a writer if he’d get me a review copy of Spaceship Warlock. Of course, from my MacWorld experiences with dad, I knew all about review copies — free software that you write about and then keep!

MacGames Digest premiered in mid-1992 with my review of Spaceship Warlock. I showed my English teacher, who was so proud to have a student published that I got some sort of award. Then there was a newspaper article about the “Teen Computer Whiz of Pittsford” that did not do very much for my social life.

1993: PowerBook 100

I was the only kid in my high school who had a laptop. Unfortunately, my “laptop” was a Tandy 100 that had been obsolete for years and had a 5 line display. Still, it was better than paper for taking notes.

In 1993, Apple dumped the remaining stock of PowerBook 100s and I somehow convinced my dad to buy me one. One notable memory was my mom’s friend (and Apple employee) Randy showing me Macsbug, the low-level debugger that was built into the OS. He said that looking at the output in Macsbug would teach me assembly language. I never actually bothered to learn anything from it, but periodically dropping into Macsbug was a great way to impress classmates by claiming I knew what all of the weird numbers and symbols meant. Also, “rb” reboots.

1994: KlepHacks

In the mid-90’s, Apple’s product line started getting weird. There were the consumer targeted “Centris” Macs, which each had non-Centris analogs. Then there were some gimmicky new concepts, like the slim and dockable PowerBook Duos. The pinnacle of gimmicks was the Centris/Quadra 660AV and Quadra 840AV. I remember seeing the announcement when I was at Stanford for a summer program for high school students. Despite being a rabid Apple fanatic, I shrugged off the voice control and software-based modem of the AV’s knowing that the elite Quadra line was out of my reach anyway. And the Duos? Come on! Who’s going to pay extra for a dock?

Of course, I ended up with both, though I’m not entirely sure how. I think the Duo was purchased through an Apple employee because I remember going to Cupertino to pick it up. All I remember about getting the Quadra is that I was bad. I did something to piss off my parents and my dad said (paraphrased), “The 660AV is in the storage box outside. It’s not coming in until you apologize to your mother.”

I put the new machines to good use. Years earlier, I had learned BASIC and used it to write text games. Now I wanted to write games for the Mac. I asked my dad what Mac games are written in and he said, “I think Pascal.” So I took a course at RIT on introductory Pascal and was surprised to find that it was just the underlying language and had nothing to do with buttons or windows. I asked dad how you learn about all that stuff and he said, “I think there’s a book called ‘Inside Macintosh'”

Inside Macintosh was more of a giant multi-volume reference than a learning guide, but I remember actually finding a copy in the bookstore at the mall and coming home excited to learn how to write Mac apps. The only part I could initially make sense of was the interface guidelines because it had pictures. The rest was a mystery. Yet somehow, over time, I figured out the basics of Mac Toolbox programming and put together a mildly interesting text editor called “Jot! A KlepHack”.

Over subsequent years and into college, I developed and shipped several shareware apps, including an Apple trivia game, a network agent tool, various HTML converters, and an email signature plugin. At its peak, KlepHacks was pulling in a few hundred dollars a month. But more than the extra pocket money, I really liked having people use the stuff I was writing.

1995: Sad Times

1995 was a horrible year for Apple products. I arrived at Stanford with a new PowerBook 5300 and it had horrible software and hardware problems. I remember it centered around the transition from MacTCP to OpenTransport. Updates kept coming out and making things worse.

It was a tough time to be an Apple advocate. I lobbied my then-girlfriend-now-wife’s dad heavily to get her a Mac for college. She got some sort of all-in-one Performa that was later recalled for having a bad motherboard.

While Stanford was still heavily Mac-focused (which was actually a huge part of why I wanted to go there), it was getting hard to defend Apple all the time.

This was the beginning of the dark times.

1996: Be and WebTV

In high school, I read a number of books about the history of the computer industry, and Apple specifically. Through books like “Hackers“, “West of Eden“, and “How to Drive the Competition Crazy“, I had come to view the people involved in these pivotal technology companies as gods.

When I arrived at Stanford, I convinced my mom’s Apple friend to introduce me to some of these people that I had read about. I remember a brunch at Hobees with several of Randy’s friends, one of whom was Paul Mercer. Paul was a legendary Apple employee who had worked on (I think) QuickDraw… or maybe QuickTime. Quick something for sure. Later he would have a huge role in the invention of the iPod.

Anyway, Paul said that he knew of some ex-Apple people doing interesting things who might want an intern. He introduced me to Bruce Leak (also legendary) at a company called Artemis Research and some folks at Be, Inc., which was founded by former Apple exec Jean-Louis Gassee. The tour of Artemis was like a dream come true. Bruce took me around the building and introduced me to all these ex-Apple people, telling me what they had built (“This guy wrote MultiFinder. This guy wrote AppleScript.”) I was in awe, but I also had no idea what Artemis did because they were still in stealth.

I was similarly star-struck at Be and took the intern gig with a vague promise to build them a web site and the lure of a possible free BeBox (which unfortunately never materialized). During my time at Be, I learned network programming from c.k. haun (legendary Apple developer of various AppleEvents stuff) and Dominic Giampaolo (file system genius). I also frequently ran into Jean-Louis Gassee, who would say “Ah! Ze web master!” when he saw me.

Artemis (the job I didn’t take) turned out to be WebTV. I ended up doing a summer internship there in 1998.

1997: Working at Apple

All I really wanted as a kid was to move to California, work at Apple, and drive a Honda Civic. In 1997, I checked off the Apple part thanks to John Lilly and Adam Nash. I give Adam credit because he made the intro to John and my Apple intern interview actually contained this exchange:

John: How do you reverse a doubly linked list without using any extra memory?
Me: Well….
John: I’m just kidding. Adam says you’re smart.

Before the internship started, John said he needed my address to send me some paperwork to sign. In what would be the highlight of a not-so-great year at Stanford, a UPS guy showed up with the just-released and oh-so-weird eMate 300 running (of course) Newton OS.

The Apple summer was a blast, but it ended on a bit of a downer since the entire group I was a part of was laid off. We were the Advanced Technology Group, or Apple Research. All summer long, there were rumors about layoffs. When we were called for a meeting one afternoon, nobody was particularly surprised that ATG was getting killed. For someone who was religious about Apple, though, seeing all those great people lose their jobs was still a shock. It took me a few years before I could believe in things again.

It made sense though. Apple was universally viewed as fucked that year. This was the year of Wired’s famous “Pray” cover. The stock was at a 10 year low. Even employees were joking that the new “Mac OS 8,” which had an ad campaign with words like “OS 8: Communicate” and “OS 8: Accelerate”, should be more like “OS 8: It’s not so great” and “OS 8: Four years too late”

1998-2001: I Switch to Windows

In late 1997, I sent a joke press release to my friends announcing my intention to switch to Windows. I had come to view Apple as just a company and not some sort of utopia. I had also seen a commercial for a new version of the game Test Drive, which I had played long ago on the Apple ][. Of course, the new incarnation was only available on Windows.

So in 1998 I switched, and the game sucked. But IE was super fast and my new PC became my main computer. And after a few months of use, I no longer cried when I started Windows.

2002-2003: Digital Lifestyle

As the years ticked by and I got more accustomed to Windows, I continued to buy Macs and keep tabs on Apple. I had a PowerBook G3 and a PowerMac G3. With every MacWorld keynote, I felt like Apple was finally back and whatever it was they announced was something I had to have. But then an hour later, the effect wore off and I’d be perfectly content with my PC.

Eventually I came to believe that there was something to be said for the “digital lifestyle” concept that Apple was pitching at the time. The notion that your computer is about storing memories, creating lasting artifacts, and adding soundtracks to your extensive collection of home movies.

But since I couldn’t stomach the price of getting all that Apple equipment, I tried to fake it in the Windows world. I got an Compaq iPaq as my PDA, a Diamond Rio PMP300 MP3 player to play digital music, I archived all my digital photos in hierarchical folders, and I tried out various video editing packages before realizing that I didn’t really have home movies or a family to record home movies of.

2004: iPod

I had resisted the Apple digital lifestyle products because I thought that cheaper equivalents existed elsewhere. But in 2004, I broke down and got an iPod Photo. For a while, I got really into podcasts and thought that Adam Curry and Dawn & Drew were the harbingers of something huge. I also started thinking a lot about the experience of listening to music and spoken word content. This was the roots of SpotDJ.

2005: XCode

My heyday of Mac programming was back in the late-90’s PowerPlant/CodeWarrior days. I wasn’t the best, but I was very good at it. My favorite teaching gig at Stanford was being a TA for CS108 because PowerPlant was so vastly complicated yet beautiful in a way. I was known for emptying out the queue of email questions from students before the other TAs even had a chance to log in.

In 2005, as I was prototyping what would become SpotDJ, I got back into Mac programming. I had kept tabs on things over the years, re-doing the same Cocoa tutorials over and over, even back when they were NeXTStep tutorials. As I got more into it, I found an elegance in Objective-C and Cocoa that was unlike anything I had used before. I’d have a similar experience a few years later with Ruby on Rails.

2006: A Less Humble Apple

I think 2006 was the first time I had been on Apple campus since I worked there as an intern in 1997. We demo’d SpotDJ to the iTunes group. They nodded politely as we told them our plans to make iTunes and iPods more social. We told them that these social features should exist within iTunes and we’d like their help in making that happen.

They politely explained that they wouldn’t provide any help and handed us some free iTunes gift cards for our trouble.

While the meeting was disappointing, it was kind of cool to see Apple once again at its prime. When I was an intern, there were probably teams from Apple going out to other companies trying to strike deals and failing. Now Apple was on top of the world and if you somehow managed to get a meeting with them, you might end up with nothing more than some free songs.

2007: No Apps on the iPhone

Most people either loved or hated the iPhone when it was announced. I was pissed off that Steve Jobs specifically said that it was based on Cocoa yet there would not be any third party apps allowed. Few even remember that there was a time when iPhones didn’t have apps.

2008: In the App Store

One of my favorite Facebook apps from Context Optional was the Reservations app we built for OpenTable, in collaboration with Facebook. I thought it was the ideal use of a branded app on a Page on Facebook. So I was eager to work again with OpenTable on their iPhone app. While I was pretty happy with the code I wrote for the initial proof of concept, we soon hired Kevin Ballard to obliterate my code and do things the right way. But regardless of whether or not any of my code survived, it was great seeing the app go live in the App Store and get highlighted by Apple.

2009-2012: Kids and iPads

My older son was never the “chuck things at the wall” type, so we let him use our iPad pretty early on. It’s interesting to see the modalities take hold so quickly. We’d notice him trying to move individual objects on a page of a book because he had come to expect it. And, like many kids, he hasn’t really taken to a mouse and keyboard (nor does he really need to yet) because touch apps are so much more intuitive.

As he’s gotten older, I’ve been seeking out apps that might open his eyes the way certain pieces of software did for me when I was a kid. In particular, I remember playing Rocky’s Boots on the Apple // and learning all about logic gates. While not really software, I believe my impeccable grammar came largely from Speak and Spell (and also from my mom, who was an English teacher).

I’ve seen some beautiful educational apps for kids. Almost too many — it’s getting hard to find quality stuff.

2013-2014: A Mac Without Compromises

If you look back at the Macs I had throughout myself, you’ll see the trend is that I always got the middle one. The LC, not the //cx. The Centris, not the Quadra. Not the best Mac, not the cheap Mac, but the prudent middle ground. Last year, however, I decided it was time to grow up and get the machine I really wanted. While it’s far from the most expensive Mac, I configured an 11″ MacBook Air with the biggest SSD they offered, the most RAM, and even the not-even-noticeable processor boost because why not?

It’s everything that every Mac I’ve owned aimed to be. A journal, a work of art, an extremely portable productivity device, a communications tool, and in some ways, a reflection of who I am.

Happy Birthday, Mac. As a special treat, I’m going to clean off all the crap on the desktop.