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Road Warrior

ROAD WARRIOR: Choosing an Operating System for the Road

Jeffrey Allen

In the not too distant past, Mac and Windows users treated each other with disaffection and derision. In those days, Windows controlled the legal market, and only a few oddballs (like me) thought the Mac OS (operating system) could work in a legal environment. I have run my law office on the Mac OS since 1985, when I networked 128k Macs using a 10 MB (yes, MB) hard drive as the server because I had some computer-phobic attorneys in the office, and I thought the Mac’s smiley face might put them at ease. Although I have consistently used the Mac OS as the primary OS in my office, I have always kept some Windows machines around to allow me to use certain software not available on the Mac platform and to allow me to test and evaluate Windows-based programs for reviews. Accordingly, I consider myself fluent in both platforms, even though I have a strong preference for the Mac OS.

Historically, the larger law firms pretty much universally standardized on Windows, notwithstanding its historic instability issues, susceptibility to attack by the bad guys, and generally less user-friendly approach to operations. Medium and smaller firms tended to follow suit, apparently thinking that the big firms must know best. Occasionally attorneys in firms with Windows-based operations would use Macs at home and would want to get them in the office, but they were reluctant to talk about it as they were concerned about the backlash they might get from their firms and IT departments. More recently, however, more and more firms have started gravitating toward the Mac.

When Apple released the iPod, things started to look up for Apple as more and more people (including attorneys) started buying Mac products. When the iPhone came out, the phenomenon grew more rapidly. Solos and small firms, having greater flexibility than large firms by the very nature of what they are, led the way, but the large firms also saw the glass ceiling shatter and Macs started to appear in the large firms as well. Now it has become fairly common for a large firm to have many attorneys using Macs in a still primarily Windows-based environment. On the other hand, more and more small firms and solo practices use the Mac OS as the primary operating system.

This little bit of history serves as an introduction to the point of this column, which appears in an issue focused on people of diverse backgrounds who have moved more directly into the mainstream of our social environment. The time has come for the Mac and Windows war to end and the users to accept each other and work cooperatively together. The two systems have evolved to the point where this can happen in the workplace. Doing this has the advantage of allowing firms to benefit easily from the diverse software available to the Mac platform as well as the software available to the Windows platform. To paraphrase the words of one social philosopher: “We can all get along!”

Now, while this is all well and good, you may ask, “What in the world has this to do with life as a road warrior?” That, in fact, qualifies as a pretty good question, so I am glad you asked it.

Windows has grown increasingly more stable and user-friendly with each passing iteration. Interestingly, some reviewers used to refer to Microsoft’s efforts at user-friendliness in Windows as “Mac-like” and considered it praise to report that a new version of Windows was the “most Mac-like yet.” Most people now consider Windows 7 fairly stable and reliable. Windows 10 has started moving into a similar position. I prefer Windows 10 to Windows 7 and have it on most of my Windows machines. As much of an improvement as Windows 10 makes to its predecessor systems, it still does not offer the same ease of use and stability that I see in the Mac OS. Why do I focus on this point? Simply to answer the question of why talk about this in a column about life as a road warrior.

When you depend on your computer for work and spend significant amounts of time out of the office, you cannot afford to lose the ability to work on your computer. A computer failure can have disastrous, if not catastrophic, impact on a road warrior’s ability to duke it out with work on the road. I used to concern myself with this problem so much that, even with the Mac OS, in the old days I used to carry around a clone of my hard drive so that I could use it to work with if my Mac laptop failed. When I traveled, I also carried a disk full of repair utilities and the ability to restore the operating system. Apple now has built a partition into the OS install process that both facilitates the repair of issues on the drive and allows you to reinstall the operating system. As a result, I no longer need to carry as much information with me when I travel. It has been so long since I had an irrecoverable failure on the road that I no longer carry a clone with me, although I do carry a copy of critical information. This, too, will stop soon, as I can pretty much accomplish the same thing using cloud-based storage.

I should point out that you can do the same thing with Windows, but I do not consider the repair and reinstall facilities on the Windows platform as robust as those on the Mac side of the house. Additionally, historically, I have had more problems with computers on the Windows platform and found these problems more difficult to recover from; and that, too, becomes a concern for a road warrior.

For these reasons, I still prefer Mac laptops as travel partners. I do have some concerns going forward, however, and I will share them with you here. Steve Jobs, shortly before his death, referred to our tech-society as a “post-PC world.” He made this comment in the wake of Apple’s introduction of the iPad and the phenomenal success it initially had. In the aftermath of this success, Apple moved the evolution of its Mac OS (computers) and its iOS (iPads and iPhones) toward each other in what some saw as an inevitable merger. We continue to see evidence of this evolution, but at a much slower pace than many anticipated. As a result, the iPad (even the iPad Pro) cannot yet run programs from the Mac OS, some of which have no iOS analog.

We also have seen the evolution of Apple hardware (especially computers) slow down to a veritable crawl. It now appears that Apple may phase out the MacBook Air (my favorite travel computer for several years). The MacBook offers a pretty face, but not as much substance (I consider it seriously underpowered). After a prolonged time, Apple has updated its MacBook Pro line, but these laptops are far heavier than the MacBook and the MacBook Air, making them less desirable for travel.

On the other hand, Microsoft (much to my surprise) released the Surface Pro (now the Surface Pro 4), which runs Windows 10 very well, presents a svelte traveling companion, and converts from a pretty fair laptop to a decent, but oversized tablet (about the same size as the larger MacBook Pro, which I find far less useful than the 9.7” model). The Surface Pro 4 gives you a good piece of both worlds, even if not the best of both worlds. Most significantly, Microsoft uses Windows 10 in a computer mode and a tablet mode on the same device and switches from one to the other with relative ease. While I still prefer the Mac OS to Windows, I have had little difficulty with Windows 10, and on the hardware side, Microsoft has made a race out of it with the Surface Pro 4. I see definite advantages for the road warrior in carrying a single device that functions as a laptop and a tablet (even if it is oversized), rather than in carrying two separate devices—although we should not ignore the obvious advantage of having a second device if the first crashes or goes missing. Apple needs to remember that when VHS videotape won the format war with Betamax, Beta more or less disappeared from the scene (then both disappeared in favor of the DVD). Vinyl ruled the roost until someone invented cassettes, which ran the show until someone came up with the CD. Now CDs and DVDs come under the category of “dinosaur” in favor of wireless streaming. Technology has one absolute: Everything changes. In some sense, however, the more things change, the more familiar the process seems.

Jeffrey Allen

Jeffrey Allen ( is the principal in the law firm of Graves & Allen in Oakland, California. A frequent speaker on technology topics, he is Editor-in-Chief of GPSolo magazine and GPSolo eReport and a member of the Board of Editors of Experience magazine.