My Mac Life

(or, “How an iPod Changed My Perspective on Technology”)

A topic I’ve been meaning to espouse on for some time is exactly how I’ve managed to go from being such a die hard geek to being somebody who enjoys using Apple’s technology (not that the two are mutually exclusive).

A close friend of mine has taken great joy in telling people how my views on technology took a dramatic shift shortly after I got an iPod, and of course while that may sound overly simplistic, it’s essentially true.

Firstly, I am what most would call an übergeek. My fascination with computers and all things technical goes back to my early childhood, when I used to hang out at the local Radio Shack and fiddle with the TRS-80’s and Tandy Colour Computers. I built my own Z-80 based machine when I was about 12, installed my first Novell NetWare network when I was about 14, and have been on the Internet since before most people even knew there was an Internet (no, kids, the World Wide Web is not the Internet).

In that time, I have always been a fairly die-hard PC user. I was never overly fond of Windows, having eschewed it in favour of OS/2 until such time as I really had no other option than to become assimilated by the great Microsoft collective (although to be fair, Windows 95 did start to look a bit promising compared to what else was out there at the time). Although I had once owned an Apple IIe, I never considered the Macintosh computers that succeeded it to be much more than toys. Sure they were great for desktop publishing and other work like that, but nothing that a real hardcore geek would ever use. An operating system without a command prompt??? What was that all about?!?

Further, in the professional world in which I worked, nobody was really out there using Macs. Windows pretty much carried the day at that time, and on the few occasions I encountered Macs in my job, they were pretty much isolated from the rest of the world — relegated to special-purpose tasks such as graphics publishing and so forth, and seldom even connected to the networks on which I tended to hang out. Mac support was seldom (if ever) required, so they could be safely ignored as those other computers that no serious computer user would ever use.

My Foray into the world of Digital Music

When the MP3 phenomenon hit in the late 90’s, I was fairly quick to jump on that bandwagon, and by Christmas 1999, I had a Creative Labs Nomad MP3 player (note that I’m not talking about the Nomad II, or Jukebox, or any of those which came later — this was the original Nomad: 32Mb of RAM and a parallel port interface to transfer your music). However, as a concept, this was very cool, and the idea of being able to carry even a few songs around on a portable player like this was something I had been wanting to do for a while.

Of course, the nature of the technology was such that I tended to replace the songs very seldom, and the Nomad gradually fell into disuse. I needed something with more capacity, and began looking at the Creative Labs Nomad Jukebox that came out a year later with a serious case of techno-lust. Of course, the price range was not particularly reasonable for me at the time, and I therefore took a “wait-and-see” approach, deciding instead on upgrading to an Iomega “HipZip” player; the 40Mb inexpensive replaceable media (Clik Discs) seemed a brilliant idea at the time — a time when 40Mb of Compact Flash memory would have set one back close to $500. Again, I used this for quite a well, but it, too, gradually fell into obscurity. I just didn’t feel like listening to the same music all the time, and changing the music just wasn’t all that convenient.

Throughout this time, I was somewhat aware of this thing called an “iPod”, but of course it was an Apple thing, for Macs only, so it never gathered much interest for me.

By early 2003 I had pretty much decided that the only way to go was with a hard-drive based player. I needed to be able to carry ALL my music around with me, all the time. Well, at that time, the only two games in town were Creative and Apple. Again, the iPod just looked a little “goofy” to me, seemed too simple, and was too much of an “Apple thing.” On the other hand, Creative had just released their 20GB Jukebox ZEN, which had portability, capacity, AND USB 2.0 transfer speeds going for it. I had always been quite happy with Creative’s stuff (even my original Nomad, not to mention a multitude of PC sound cards and other accessories), so I took the plunge and picked one up.

At that time, my entire music library fit nicely into 20MB, with quite a bit of storage space left over. The Jukebox ZEN itself worked quite well, with a reasonably decent menu system, albeit a small screen, and pretty reasonable sound quality. The software on the other hand, was much less intuitive. Creative bundled their own software application, and for a time I wrestled with it until eventually picking up a replacement in Red Chair’s Notmad Explorer. Notmad seemed like a simple enough concept — manage the content on your Jukebox as you would any other file system, replacing a tag-based index for a file and folder structure. Bi-directional drag-and-drop was supported, and even something of a “sync” feature that would do it’s best to synchronize with a hard-drive based music library, although success with that was often limited, and the number of options available for file naming and syncing just proved that sometimes you can have too many choices.

While the Jukebox itself worked well, the hassles with getting music on and off of it, and the fact that the interface wasn’t quite intuitive (small screen, too many menu layers, etc), meant that it too didn’t get used as much as I would have liked. Of course, the fact that it wasn’t the smallest of devices didn’t really help either.

It really wasn’t that I didn’t know how to manage my music, as I am a very technically literate person; the reality was that I just really couldn’t be bothered — there were things that I would much rather be doing with my time than organizing, transferring, and cataloguing my songs, or messing with software applications that didn’t quite work as well as they should.

During this time, I also experimented with a number of home digital media systems — devices designed to take music from a computer’s hard drive and stream it over a wireless network link to a home stereo system or other remote speakers. My use of the Creative Nomad prompted me to pick up the Creative Wireless Music System, since again this seemed like a good solution at the time. However, that experience proved to me that Creative Labs, while they may know digital sound equipment, most definitely did not excel in the area of wireless networking. My second device was the Linksys Wireless Media Adapter, which seemed to have the reverse problem (Linksys, of course, knew how to build a networking device, but the PC-based software and on-screen menu firmware was limited almost to the point of being frustrating).

In looking for a better solution in that area, I eventually came across the SlimDevices Squeezebox. I ordered one of these, and within a few days had ordered a second one, replacing both my Creative and Linksys devices without hesitation. The Squeezebox had the advantage of on-device displays and menus, as well as a very good server-based software to catalog music and control the devices.

It was this foray into SlimDevices that I think first made me take a look at iTunes. One weekend, as I was exploring the various options and plugins for the SlimServer, I came across some neat features related to iTunes integration. Having long ago developed a disdain for most of the other options for music management on a Windows PC, I decided to download iTunes and take a look.

The next morning I went out and bought an iPod.

The Thin Edge of the Wedge

The fact is that the simplicity and intuitiveness of iTunes demonstrated the problem that I had been having all along — I was spending more time managing my music than actually listening to it. I had always known that Apple prided themselves on making simple and user-friendly apps, but I had always associated “user-friendly” in that context with “unsophisticated.” While iTunes didn’t necessarily have every feature that one could think of, the necessary stuff was all there, and it was there in a very easy-to-use fashion. Where most Windows-based music library software had you worrying about file names and directories and the underlying file system, iTunes took the logical step of insulating the user from that, concentrating instead on organizing music by indexed tag information. Certainly, the files still had to go somewhere, but as the end-user managing the music through iTunes, those were details I didn’t need to know or care about beyond giving it a common library location.

Of course, being a technical user, I explored all of the facets of iTunes, and spent some time going under the hood and looking at the database files and seeing what I could do with it. However, those were things I did because I wanted to, not because I had to.

Further, the integration with the SlimServer devices was brilliant. I came home one day after creating an On-The-Go playlist on my iPod, dropped by iPod into the dock, and by the time I got to the living room, the playlist was available on my Squeezebox.

To me, this was the first foray into a realm where things “just worked” It identified something I had been striving for in my use of technology for many years: The idea that technology should simplify our lives, not complicate them. While it’s okay, even beneficial to understand technology, it shouldn’t be a prerequisite, any more than driving a car should require knowledge of auto mechanics.

The simplicity of the iPod solution became even more apparent when I handed my iPod to my wife, who is most certainly not a technology person, and she was able to navigate it and figure out how to access all of the basic functions in under 30 seconds.

Around this same time, I also transitioned from a Palm Tungsten T3 to a Blackberry device for much the same reasons. While Palm OS could do a whole lot of really neat and cool things, getting it to manage the important details of my life was often more of a struggle than it was worth. Like my music, I was spending more time managing my calendar than actually following it. The Blackberry, on the other hand (with an Exchange server on the back-end) was another example of technology that “just worked.”

Contemplating a Switch

At that point, the rather nebulous concept of making the transition for Windows to Mac OS X started to become a bit more firm in my mind. I had played with Powerbooks at a couple of local Apple resellers while shopping for iPod accessories (there were no “Apple Stores” in Toronto in those days), and I really liked what I saw. In fact, on one occasion I even went over to the online Apple Store and configured a Powerbook for my needs so I could get an idea of what I’d be looking to spend.

In addition, the fact that OS X was in reality a derivative of BSD Unix “under the hood” was in and of itself very appealing. I had been playing with Linux for about seven years at that point, and I really liked some of the things that I could do with it. Unfortunately, despite numerous attempts by the Linux community to produce a decent GUI, driver support, and business productivity applications, Linux itself still fell short as a desktop OS. I ended up keeping a dual-boot configuration around so I could boot up Windows to do my day-to-day work, and Linux when I wanted to do more “low-level” networking and programming stuff.

Ultimately, though, the problem was that as sexy and powerful as Mac OS X looked, the question I still had to answer was whether somebody in my particular line of work could actually take the plunge without losing too much of the functionality I had come to know and love from my Windows world…

The Next Step…

Despite the Powerbook having a great appeal, the combination of potentially losing functionality and the price point itself prevented me from ever really exploring it until almost nine months later.

During the summer of 2005, I purchased a pair of new laptops for my wife and I, and by that time I had mostly abandoned the concept of making the switch to OS X. I was embroiled in the use of a number of Windows applications, from Microsoft Office to Project to Visio, not to mention a number of networking related tools, all of which just made a transition to OS X seem impractical at best.

However, later that summer, it occurred to me that I should get a dedicated “music server” for my Squeezebox devices, since I was now relying more and more on a laptop, my desktop computer (which had traditionally done the job), would not always be on, and would be performing other tasks. For this purpose, a Mac Mini seemed an ideal solution — SlimServer would run on OS X, iTunes of course lives on OS X, and I doubted that I would find a Windows or Linux-based machine with as small of a footprint as a Mac Mini at even twice the price. I also figured this would be a good chance to play with OS X a bit more, but that was really a secondary consideration.

So in late August, the Mac Mini came in, and I set it up with all of the necessary software to support my digital music collection, both for streaming to the Squeezeboxes and syncing my iPods. The idea was that this would be a box that would sit rather unobtrusively in the corner, and not be used for much else.

However, something happened in the process of setting this box up. I began to explore Mac OS X more fully, and I began to explore the Unix capabilities of the box (after all, SlimServer was heavily based in the Apache and Perl space, and required a little bit of Unix-geeking to get running properly). The combination of power and simplicity once again impressed me.

In addition, Apple had quite cleverly bundled a trial edition of Microsoft Office 2004 for Mac. I had always had vague ideas of Office being available for the Mac, but hadn’t really explored it until now. I fired up Word and Excel, opened a few of my documents (across the network from my Windows PC, which was also surprisingly simple, considering I hadn’t actually configured any networking client of any kind on the Mini), and they came across without a character out of place.

Word and Excel compatibility aside, however (since I really expected that would be fine), the burning question in my mind was still the e-mail issue — or more specifically the groupware issue. In most corporate and professional environments, there is more to business services than just e-mail; calendars, shared folders, address books, etc., all have to be accounted for. My world in that area ran on an Exchange server, and the ability of the Mac to handle this was probably my biggest concern…. Sure I can do e-mail via IMAP, but what about my calendar? I knew from reading the back of an Office 2004 box that it came with this thing called “Entourage”, but wasn’t entirely certain of it’s compatibility with something like an Exchange server.

Well, fortunately for me, Microsoft had made great strides in the few months before this in improving Entourage’s compatibility with Exchange. I fired up the Entourage client on my Mac Mini, plugged in a few basic configuration values, and suddenly my whole Exchange mailbox was just “there”…. Including my calendar and my address book.

The discovery of Entourage was the last major hurdle to my acceptance of Mac OS X as a viable alternative to my years on Windows. The existence of Virtual PC was the other one, and I had been aware of that particular option for some time, but while that would be fine for less frequently used apps like Visio and Project I was not about to buy a Mac just to leave a Virtual PC session running all the time for my e-mail client.

After about two more weeks of playing with the Mac Mini, I had made my decision to go shopping for a Powerbook.

The Switch

The fact that I had only two months prior bought a new Windows laptop caused some consternation — mostly with my wife, who really didn’t see the point in going out and spending more money, but the economics of the situation eventually won out — The Windows laptop was new enough to go on eBay and still be able to recover a significant portion of the purchase price. Ditto for the Mac Mini, which I decided would not be required in my new configuration either. These would fund the Powerbook purchase, so off I went to the Apple Store (we had one by that time) in late September.

Along with the Powerbook was a purchase of Microsoft Office 2004, Virtual PC, and a multitude of other accessories. Office 2004 would form my staple set of applications, and I decided that Virtual PC would supply compatibility with any Windows applications that would otherwise be left behind (the two most notable being Visio and Project from a business productivity point of view).

In the process, however, the lure of bundled software again proved useful. The Powerbook came with a version of OmniGraffle pre-installed, and for my purposes this simply blew Visio out of the water for ease of use. So, another software package went onto the back shelf. In addition, my needs for project planning were usually far simpler than to require Microsoft Project, so the bundled OmniOutliner would also meet those basic needs (although both OmniGraffle and OmniOutliner were quickly upgraded to the Pro versions).

Suddenly, I found that Virtual PC wasn’t as necessary as I had thought. I still needed it for testing certain applications, and dealing with certain specific networking tools (working with administrative tools on Novell NetWare and Windows networks, for instance), but I would really have no need to load it up or live in it on any kind of regular basis.

In the process as well, I also fell in love with Keynote. While Word and Excel were required for compatibility with my Windows-laden colleagues, I generally didn’t do much collaborative work on presentations, so putting them together in Keynote would be just fine. If somebody wanted a copy of the presentation for reference, I could export to Powerpoint, or simply save as a PDF. I found Keynote to be far easier to use than Powerpoint, and the graphics were a lot smoother and cleaner, particularly where animations and transition effects were involved.

In addition, over the next few months I had a bit of a love-hate relationship with Entourage, particularly in relation to the built-in iApps (Mail/iCal/etc), but that’s a story for another day.

The bottom line is that I very quickly became hooked, and as I discovered more and more OS X native applications that would do what I needed and wanted, my satisfaction with OS X only increased. Ultimately, I had a machine that would be the best of three different worlds: The very user-friendly, intuitive and aesthetically pleasing OS X GUI, the raw, unbridled power of Unix under the hood, and the ability to fall back to Windows for those things that still required that world.

My OS X experience has not been perfect. There are still some idiosyncrasies and stability problems sometimes, but these are far more rare than experienced in Windows. In addition, Apple’s design of OS X has done some clever things to decrease user frustration, whether intentionally or not; for example, when an application is busy or has stopped responding, the graphic rendering of the application continues to work beautifully. The window itself may not update (as the application is busy or frozen), but it can still be moved around, minimized, and resized, and does not interfere with the rest of the user’s experience. It’s a little thing, but seeing half-drawn windows of hung applications on Windows was always something that I found extremely frustrating — it gave a feel of something being broken or “not quite right” when this happened, and it was often impossible to drag another window out of the way to see what the hung app was doing last.

At the end of the day, it may not be all wine and roses, but the fact is that I find the OS X solution to be more powerful, easier to use, and overall a far more pleasant experience than struggling with Windows. Again, technology that simplifies my life, rather than complicating it further; OS X lets me go under the hood when I want to, but doesn’t force me to on a daily basis, with the result being that I can generally get more productive work done, and have fun at the same time.