General Practice, Solo & Small Firm Division

A service of the ABA General Practice, Solo & Small Firm Division

Technology eReport

American Bar Association - Defending Liberty, Pursuing Justice

September 2008

Vol. 7, No. 3


  • How to Set Up a Law Firm Website »
    Should you do it yourself, or hire a pro?
  • One Lawyer's Journey from the Dark Side:
    Leaving Microsoft and Learning to Love the Mac

    Vista was the straw that broke the camel’s back. How the transition worked out.


One Lawyer’s Journey from the Dark Side: Leaving Microsoft and Learning to Love the Mac

Computers are central to my life as a lawyer. Not having a secretary, I sit at my computer for nearly the entire day. I communicate with clients by email, I type my own documents, and I used to live with an almost constant subliminal rage.

I referred to it as the wheel-spinning ratio: the ratio of time trying to fix something on the computer over productive time. Time wasted researching some glitch in a piece of software. Frustrating time spent on the phone talking to tech support trying to find out why a computer won’t recognize a brand-new printer. And so on and so on. In a two-man office, I am both my own CIO and tech support. I even have a degree in computer engineering. Over the years, the wheel-spinning ratio seemed only to grow larger. I grew paranoid: I expected my computer to fail on me at the most inopportune moment. I knew my computer could sense when I needed it the most, and it was then that it was most likely to fail.

I grew tired of the constant intrusion into my thoughts by a computer determined to get me to download an update. I grew frustrated and angry when I instructed a computer to do something only to be asked “Do you really want to . . . ?” And when Vista came out, I knew I had reached my limit.

Not only did fully a third of my existing software not work, not only did I have to wait and acquire new drivers for all of my peripheral devices . . . now when I asked it to do something, not only would it ask “Do you really want to install this,” it then would tell me I needed administrator rights to do it, notwithstanding that I was the administrator. It told me there were places on my own computer I did not have permission to go. It insisted on making random directories read only and wouldn’t let me change that.

I had had enough of the Evil Empire. There had to be a better way.

As I passed an unfamiliar computer store, I noticed an eerie a glow coming from the windows. There was a computer in the window with crisp clear lines. It beckoned: It was a Mac.

I was nervous. I was used to the Microsoft world and something of an expert in it. If I bought a Mac, I would be a stranger in a strange land. Would I be able to learn this strange new operating system? Would I be able to find the applications I needed to run my law practice? I was to learn that the Mac was a gentle taskmistress.

I was reassured. Macs came with Intel microprocessors that allowed them to run Microsoft Windows applications. So I could make the transfer to the Mac world while hanging onto the crutch of my familiar Windows applications.

Macs worked differently from Windows. It seemed at first as if everything it did was the opposite of my familiar Microsoft world. Instead of having a window in which an application resided along with all of its menus, on the Mac the menus were always at the top of the screen. Whatever program had focus, that was the menu that appeared at the top of the screen. At first it seemed nonsensical, but now it seems normal.

You couldn’t just unplug peripheral devices: You had to tell the Mac that you were unplugging something, or it would scold you. At first this was annoying, but now it seems right. It makes me a bit more thoughtful.

Dealing with the CD/DVD drive was harder. I kept looking for the application that would allow me to burn a DVD. It doesn’t exist on the Mac operating system. But it said on the box I could burn DVDs! No extra software needed. And I am not the kind of man who easily turns to the help menu. (I don’t ask directions when I drive, either.) It turned out that the disc burner was built into the operating system. All I had to do was right-click on the desktop and create a burn folder. I move whatever I want burned into the burn folder and tell it to burn away.

This made me curious to look into the applications folder that came with the operating system. There were all sorts of neat little programs, most of which I didn’t care about but that would appeal to children. Or help me play music. (I still don’t like iTunes—I prefer the way I want to organize my music to the way iTunes insists it be done.) There were programs for taking pictures and editing them. The camera is built right into the Mac at the top of the screen. Indeed, on my iMac, the computer is the screen. There is no outside box to which my monitor must be connected. It saves all kinds of desktop real estate. I no longer had to buy a program to take screen shots, as the capability was built into the operating system.

And what was most delightful to me was, the longer I used the Mac, the lower became my background level of rage. The Mac just worked. The wheel-spinning ratio dropped nearly to zero. For the first time in years, the computer had become a delightful tool, aesthetically pleasing and regularly useful.

Nevertheless, there remained certain issues. I had a vast archive of email messages and an address book that had to be ported into my Mac. I was a long-time Outlook user, and I wanted to have the same functionality to which I was accustomed. Fortunately, Microsoft had a native Mac program: Microsoft Office. Word on the Mac ran almost identically to Word on the PC. And while the Mac version of Office had a similar email and address book program, it had a different name (Entourage) and couldn’t import Outlook files directly. Microsoft hadn’t thought of that. Go figure.

I found an inexpensive utility program called O2M published by Little Machines.($10, available for download only at No bells and whistles, probably will only be used once, but cheap and effective! In a short while, running in the background, over eight gigs of archived mail, attachments, and address book entries had been imported into Entourage, and I was off and running.

There still remained a few Windows applications I could not live without. I have a patent practice, and do many of my own drawings. I was used to using Corel Draw and Visio, neither of which exist in the Mac world. I knew that the Macintosh had an option called Boot Camp that would allow me to dual boot my computer: I could boot into the Apple operating system, or I could boot into Windows to run my Windows apps. This would solve the problem of having a machine on which I could run my necessary evil Windows applications, but in a circumstance where the Mac world could not directly communicate with the Windows world. I would have to do my Windows stuff, then reboot my computer to get to the Mac. If I wanted my email while in Windows, I would have to reboot to get to my email handler, or get my email in Windows without removing it from the server so I could get it again when back in the home world of the Mac. I didn’t want to have to live with such frustration.

Enter the wonderful world of virtual computing. A program called Parallels existed that could create a virtual machine space operating within the Apple operating system. I could load Windows into the virtual machine space, and load my Windows applications into my virtual Windows machine. The Mac operating system and the Windows operating system could coexist in peace and harmony. What was even better, I could drag and drop between Windows applications and Mac applications with impunity. Windows applications appeared just as if they were Mac applications (except the location of their toolbar, which still appeared the Windows way). In coherence mode, Windows no longer even appeared in its own separate window—it just was there, invisibly haunting in the background, ready to operate a Windows application. The interface between Mac and Windows was nearly invisible. (And yet . . . I could never shake the fear that when running Windows, it would still find a way to cause me problems.) (Parallels list price $79.99 downloadable from Street prices vary. See also VMware’s Fusion for the same price at

Although the virtual world was wonderful, it has limits. I regularly use Dragon NaturallySpeaking, a voice dictation system. As you might guess, a voice dictation program is both hardware and software intensive. It proved to be too much for my virtual machine. It ran too slowly to transcribe my dictation accurately. As a consequence, I had a choice to make: Make a dual-boot partition and do dictation only when in a Windows partition, or keep one of my PCs around just to do dictation. I chose the latter for my desktop, and dual boot for my laptop so I can do dictation while on the road. While playing Road Warrior, I can handle a minor amount of inconvenience. I’m dictating this article on a tiny PC laptop, which I pull out whenever I need to do dictation.

While I dictate, my Mac is right there bringing down my email and quietly reassuring me that I have made the right decision moving to the Mac. The technology is running quietly, unobtrusively, and flawlessly.

I think I can see Luke Skywalker on the horizon.

Dan Coolidge is a principle at Coolidge & Graves in Unity, New Hampshire. He can be reached at .

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