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The Big Switch from Windows to Mac OS X

After spending most of my computing life exclusively on Windows, I’ve made the switch to a Mac. Why now? Over the years, I’ve become quite adept and comfortable in Windows. I’ve focused much of my career around Windows technologies. So why the switch now, especially with Microsoft’s Vista launching?

Let me try to explain. But first, I know what you’re thinking. Why must every new switcher to a Mac, write about it in their blog? Why do they all start sounding like Apple fanboys from the moment they switch? I’ll tell you why new switchers to Macs get excited – everything just works. After a few days of working through the newness of everything, I’m easily more productive than I was on Windows XP. And that wasn’t a horrible operating system all things considered. But Mac OS X is just smooth, especially if you like the efficiency of using keyboard commands instead of endlessly hunting for applications and menu items. My current Windows laptop had slowed to a crawl (as usual) after less than two years. When I did some research and realized that I would be unable to run Vista well with my existing laptop, I finally decided to look at all the alternatives.

The research
Before switching, I did a lot of research. If anything, I was a Mac hater. I was one of those people who insulted Mac users without ever even having used one for enough time to make an informed decision. My recent experiences lead me to believe that most of those who are so vehemently opposed to Macs are uninformed just like I was. There’s nothing wrong with preferring Windows to Macs. You can’t dispute a personal choice. But to hold such staunch opinions without actually taking the time to use and learn the OS isn’t rational. So after seeing all the positives regarding Macs, I decided to dive in and really find out what was going on.

While I was at it, I read a lot about the Ubuntu Linux distribution and decided to compare it against Windows XP and Mac OS X. The first thing I did was make a list of all the applications I used on a regular basis. In my opinion, this is one of the best ways to evaluate whether you can actually switch and be happy (as well as productive). For the vast majority of users, the applications are the point of using a computer. So I attempted to find what apps already existed for my potential new operating system and which have equivalents. My definition of “equivalent” may be quite different from yours though. For example, from the research I did, there is no equivalent to Quicken. Period. There are applications on all three platforms that help with your personal finances, but nothing comes close to the functionality provided by the recent versions of Quicken.

I installed Ubuntu on a relatively new, low-end Dell box and tried to use it as much as possible for two weeks. While Ubuntu is rock solid (it’s been up and running for a month now with no reboots), the applications are just not there yet for the average user. and Firefox run as expected, but that was about it for me. I thought software like Wine or CrossOver, would allow me to run the Windows programs I needed (like FeedDemon), but I had real trouble getting either to work correctly. While I liked the idea of Ubuntu and was glad to hear about many others switching, I found it just wasn’t ready for prime time. Ubuntu may never reach the status of an operating system for the average user and that may be a good thing. But Ubuntu may not have to achieve that goal to be successful. The simple fact that I could consider Ubuntu as an actual option shows they’re made considerable progress with a desktop focused Linux distro. If your needs are basic (web browsing and basic office type apps) or you’re a Linux person, Ubuntu may be for you.

The applications
Installing iTunes on my Windows laptop made me buy an iPod. Initially, I couldn’t understand why everyone loved them. If you compare a list of MP3 player features, the iPod never wins. It’s unparalleled in the user experience though and this makes all the difference, Take a technology that is reasonably complex and make it dead simple to use. iTunes just worked in a way that Windows Media Player never could. This finally opened my eyes to what Apple was doing. The same process led me to the Mac. Once again I started seeing all the excellent applications available for the Mac. After keenly watching and learning about Macs over the past year, I became quite envious of the software available.

Going back to my application comparison list, all the applications I needed (plus those that I wanted) were on the Mac. Not only were most of my regular applications already on Mac OS X, but there were numerous ones I found vastly superior to their counterparts on the Windows platform. A short list of these include Keynote, Pages, Adium, OmniOutliner, and ecto. I also don’t miss Outlook, as I now prefer the distributed three piece combo of Mail, iCal, and Address Book much better. I decided to skip Entourage altogether. Interestingly, I find the Mac version of Office just as frustrating as the Windows version so I’m weaning myself from it altogether.

What made the switch to Mac OS X a no-brainer was Parallels. This software enables you to run Windows and its applications on your Mac. I’m not talking about a dual-boot here. You can literally have a Windows app on your desktop right beside a native Mac app. Easily run Windows and Mac on the same laptop. Talk about the best of both worlds. The impact of Apple moving to the Intel chips is just starting to really hit home for me. Windows on my Mac runs better than it did on my Dell. Of course, my MacBook Pro is a more powerful peice of hardware overall, but nonetheless it’s impressive.

Ruby on Rails
The final piece of the puzzle was Ruby on Rails. As my company began moving away from developing software in Microsoft .NET to Ruby on Rails, a few things became quite apparent. Even though Rails development on Windows is fine, there a some better tools available for the Mac. Specifically, TextMate is a superb peice of software that has abolutely no comparison in Windows. Additionally, the Rails core team and many Rails developers work on Mac. Oddly enough, in this community, Macs are in the majority.

Over time, I’ll be following this post up with a few more related ones. I’ll discuss specifically what I really love about my new Mac and another on the drawbacks. Coming from Windows, the Mac transition is not as easy as some would make you believe. So, in an attempt at balanced coverage, I will talk about both after using my Mac on a regular basis a bit longer.

While I’ve switched to a Mac, I doubt I’ll ever be able to completely move away from Windows (though I hope to at some point). This is why I think Parallels is such a game changer. It removes all the final excuses a potential switcher may have. If you’re in the market for a new computer, do yourself a favor and at least check out a Mac. I’ll save my rant on why Macs are not more expensive than equivalent Windows machines for a later day.

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  1. I made this switch, oh, about five years ago now. I found it very useful to blog about all the things that irritated me about Macs, because in at least half the cases, the result was that someone would comment to say ‘ah, that’s because you’re looking at the problem in a Windows-centric way; there’s actually a simple Mac-like solution’. Of course, I cannot remember what *any* of these are now that I’ve internalised Mac-ish-ness. And for some of the most obvious ones, they got sorted out in later versions of OS X. Were it not for one bit of indispensable Windows-only freeware (er, Stereo Photo Maker, I have weird hobbies), I’d be completely Windows-free now.

  2. Alison,
    Search on VersionTracker for “stereo” and you get a list of software that sounds (to me, at least) like it does something similar to Stereo Photo Maker. Perhaps they aren’t as good, but I thought I’d mention that. Here’s the search on VT I tried.

  3. I would like to hear more about how Ubuntu failed to meet your needs. Was it the tax software, and could you not get it working with the Wine/Crossover code? The more details on people deciding against Linux provides developers more data points on where “desktop Linux” needs to improve. Good fortune with your switch to Apple, but I might caution that Mac OS also has the proprietary vendor lock-in that made you switch away from XP/Vista.

  4. It’s interesting how people now feel compelled to blog about the experience. I suppose it’s the equivalent of just telling other people. I switched in the “Dark Days” (1995), so there weren’t blogs back then. Then, as now, people got to know Macs from word of mouth. I’ve been a Mac user since then, through the down and then the up because the user experience on the Mac made a lot more sense to me than the Windows experience. I don’t want to sound like I’m belittling your experience, but frankly, the majority of people in the world don’t care because they’re happy with mediocrity. All they know is Windows and will most likely never come in contact with a Mac. You recognized that you hated Macs without even really knowing them. I think most of the population suffers from the same phobia: fear (and hatred) of the unknown. And the source is hard to pin down, but mostly it’s because that’s all they have been exposed to, so they don’t seek or know to seek any better. I don’t try as much as I used to to make a case for switching to the Mac. I think they’re good products that most people won’t try. BTW, I worked for Apple in retail sales for four years up until recently. I got tired of people calling the Apple Store, the “iPod Store.” I own an Intel iMac now with both Mac OS X and Windows XP.

  5. Matthew, in your comment you say: “Good fortune with your switch to Apple, but I might caution that Mac OS also has the proprietary vendor lock-in that made you switch away from XP/Vista.”
    That is rather presumptuous of you. Tom makes it clear that he was looking for a smoother user experience, one that just works. He never said he wanted to use the Mac because of “vendor lock-in” on Windows. Instead of discounting his experience, shouldn’t you be encouraging the Linux developers to: a. have an OS that “just Works” and smoothly, and b. has a valuable suite of applications?

  6. Man. Macs are great. I’ve gotta desktop at work and its a pitty I cant afford to buy one for home! I just hope to my wildest dreams that Apple would realese Mac OSX for PCs. That would be the killer app to Microsoft. Lol!

  7. Hell yeah! Another one finds the light at the end of the tunnel! Welcome to the Mac World Tom! You could not have said it any better then this as for reasons to switch!

  8. Great article. As Mac user since 84 I stopped arguing already a long time. This article is based on user facts an that is what counts.

  9. I switched to mac about a month ago after having used damn small linux for over a year.

    I started with a macbook as a test machine but quickly realized this was how I wanted to work – especially with having the options to run some old windows apps and have a DSL virtual machine in case I needed it in parallels – so bought an imac as my main machine.

    I started using openoffice but in the end there were too many compromises in terms of the way it works – always felt like a round peg in a square hole how it runs in X11. I’ve moved to thinkfree office which is excellent.

    the other really nice touch is the built in support for an external monitor (via the mini=dvi connector) to extend the workspace in the macbook and imac.

  10. Well done on switching away from Windows. It can be a difficult task at first but you soon get used to not having to fight the OS to do your work.

    I switched from Windows to Linux full time around 2000/2001 and haven’t looked back. For me, the most important aspect of my main computer is the ability to configure it to do what I want, when I want it and in the way I find most suitable. Linux gave me that power and now working on a Windows machine in the office is just painful.

    I cannot use an Apple computer, believe me I have tried. I have a mac mini which I bought to evaluate MAC OS X a few years ago and found that the UI really got in the way of what I wanted to do. I found myself in the terminal window pretty much all the time. Which is why it runs SuSE these days.

    Anyway, once again, congrats on leaving Windows. When you get sick of the Mac, Linux will be waiting for you ๐Ÿ˜‰

  11. na i no why u really switched cause your a fat ass dumb prick that cant use a commputer right, so you buy a mac so u have to think less…. and limiting your options on flexibility of get the best out of your computer… good on ya ….. wanka

  12. @Alison – Thanks for the encouragement. I’ll keep blogging about the issues I encounter.

    @Matthew – Ubuntu failed my needs the same way Windows did – the applications. I was looking for applications designed better and more efficiently. An overall better user experience coupled with the ability to be more productive. I found more of those apps on the Mac. Regarding proprietary vendor lock-in, this was not a reason I moved away from Windows so that’s not a major factor for me. My recommendation for Linux would be to focus on “killer apps” unique to Linux desktop. Most of what I found for Linux always compared itself to a related Windows or Mac software. It may be better for Linux developers to get away from that mindset (trying to make equivalents) and focus on what makes Linux better.

    @Mario – Great points. I would just say that blogging really is word of mouth just on a bigger scale. As I mentioned above, I have no issue with people preferring Windows. Just try all the major OS’s first, then make a decision.

    @Bob – Wow, a longtime Mac user. The last Apple computer I used before my MacBook Pro was an Apple IIc.

    @Dave – Very nice article. It looks like I echoed many of the same ideas.

  13. @Paul – Try NeoOffice. It’s a port of OpenOffice for Mac. NeoOffice has been running smoothly with no issues pulling in and editing existing Microsoft Office files.

    @Jimmy – I bought a Mac so I could think more. IMO, there is considerably more flexibility in a Mac than Windows. Maybe not as much as Linux, but I guess that depends on your definition…

  14. Yeah, I was a long-time Windows user, and Linux too- several flavors. I love Linux- for my servers. It never really lived up to the promise of a nice desktop machine.

    All the press about Vista made me cringe- it seems like every release of Windows is “More secure, easier to use” blah blah blah. And I always end up with bolt-on unix utilities to make up for key deficiencies. Hey, I’m a power user.

    Then I bought a Mac for my mom. Mostly because it’s supposed to be easier to use for newbies and less susceptible to malware. Within 2 hours of using her machine, I had ordered a Mac Pro for myself.

    Apple has done an amazing thing with OS X. It’s an incredibly user friendly, highly polished and refined user interface on top of real, hard core BSD UNIX. It’s a real class act too, right from the box.

    Now I’m replacing ALL the computers in my company with Macs (Except for the servers, they’re still Linux, Slackware)

    — Ron Toms

  15. As an alternative to MS Office, I’m a big fan of Mariner Write and Mariner Calc. They’re not quite as user friendly as, say, Pages, but they’re rock solid and faster. Not to mention cheaper. NeoOffice is good, and free, but it’s too slow for me. I got tired of waiting several minutes for documents to load on my iBook, so I bought Mariner Write, which opened everything I threw at it in seconds.

  16. Here’s how I took your reason for switching to be vendor lock-in:

    “So why the switch now, especially with Microsoftรข??s Vista launching?”

    “My current Windows laptop had slowed to a crawl (as usual) after less than two years. When I did some research and realized that I would be unable to run Vista well with my existing laptop, I finally decided to look at all the alternatives.”

    Did I misunderstand the text above? I wasn’t trying to put words in your mouth.

  17. @Jimmy:

    Beautifully written and cogently argued.


    It *is* a nice change, isn’t it? I’ve been a windows user/tech for several years and when I bought my mac mini last year it took a little getting used to at first, coming from a windows-centric world. But now I enjoy working *with* my computer so much more than working *on* it.

    Nice article, and welcome to The Better Way.

  18. I’m sure if you were a FeedDemon fan that you’ve discovered NetNewsWire, it’s one of several excellent mac feed readers. MarsEdit by the same company is a great blog post editor.

    Other programs on the short list would be:

    lauchbar (or alternately quicksilver)

    mailacton (allows for mai.appl automation)

    bbedit which is textmate’s big brother

    marc linyage’s prebuilt mysql, php, and imagemagick packages can save a bit of time.

    Also if you ever do any css coding, cssedit is the best css editor on any platform…

    I understand your microsoft aversion, but word and excel on the mac are actually pretty darned good as long as you turn off all the defaults that do automatic word completion and formatting. NeoOffice is a noble effort but still a long way from feeling like finished polished Mac software.

    Don’t know if you feel like it, but it might be interesting to find how how you’ve set up your ruby dev environment and any issues you’ve had… compared to what you have on the PC.

    For example did you use locamotive or install all the parts yourself… and what’s been your experience with the various components in the mac environment vs the windows environment…

  19. Nice move. A lot of Webmailers swear by Mac these days. I’m loving my Ubuntu, but there is definitely a learning curve. And small quaky things have consumed a lot of my time trying to figure out how to adjust. But the learning curve is part of the fun.

  20. Firstly, Jimmy – You’re the first person to criticise Tom on his blog rant. Other people have stated their opinions, not always for the mac way of things, but they’re polite, understanding, and open-minded. You’re none of that, you’re purposely trying to offend him, and you really cannot spell. I doubt you’ve ever used a mac. If you have, however, you didn’t let yourself like it – you just followed what you’ve heard from most people. If you were a mac user and had never used Windows, and were one day made to use it for 10 minutes, you would be clueless and you would hate it. Don’t think I’m wrong. You say that by buying a mac he can think less… well you’re kinda right. But it’s not a negative thing. Mac OS X is not a dumbed down operating system. It just works – unlike Windows, so often. Yeah you probably know how to fix/ignore the little problems you have with Windows, but with a mac those problems just don’t happen. Options and flexibility are certainly still there with a mac. If anything, they’re more prominent. I’m starting to sound a bit closed minded, but I guess I’m just irritated about your arrogance and ignorance. I would love it if you had to use a mac for a month for your everyday tasks, so I could laugh at the shock you would be in as you begin to realise it’s not so bad. C’mon, just give it a go.

    Secondly, nice rant Tom – congratulations. I hope to soon be able to afford to buy an Intel Mac of some sort (perhaps a MacBook/Pro). Sorry about this huge comment, Jimmy ticked me off a little lol.

  21. @Jclark – Thanks, I’ll have to look into Mariner’s products. I’ll also take a look at the new Office for Mac which is supposed to be out in the second half of this year.

    @Matthew – I think the misunderstanding on vendor lock-in was my comment regarding Vista. I was simply adding to my analysis on my situation in that if I wanted to upgrade my computing experience (Vista, Mac, or Ubuntu), a move to Vista would involve a new hardware purchase just like the Mac would. Thus, I could justify new hardware purchase when comparing those two options. I initially was hopeful that I could skip buying new hardware and go straight to Ubuntu on my Dell laptop. While I found no issues running Ubuntu on my laptop, I did not find the applications and overall experience to be what I was looking for. I was however very impressed with Ubuntu. Having tried other Linux distros in the past, Ubuntu was a pleasant surprise and will only get better. So, while vendor lock-in is an issue, I wasn’t one I was considering .

    @Raul – I still feel FeedDemon is head and shoulders the best feed reader out there regardless of platform (I have honestly tried every one I could find on each of the major platforms including web-based). I hope the next version of NetNewsWire can compare with FeedDemon. Until then, I’m using Parallels w/Coherence mode to use FeedDemon on my Mac. And it works wonderfully.

    With respect to my Ruby dev environment, I looked at both rolling my own and Locomotive. Since I went the full install route when I was on Windows, I did the same with the Mac. I followed a tutorial ( as recommended by the AWDWR book.

    So far it’s working fine, I’m just still trying to get used to some of the permission issues I never had to deal with on Windows.

    @Bill – Thanks. BTW, nice recent post on your switch to Ubuntu ( as well.

  22. Hey Tom,
    We met several months back up at Knowledgeworks. You made the right move getting a Mac. I’ve never had anything but. And you know, you rarely hear about anyone going the other direction, from Mac to PC. Just like you rarely hear a waitress say, “Is Coke okay?” when they order a Pepsi.

    Let’s talk soon,

  23. My main problem with switching to apple, is that it means less choice about what kind of hardware I run my pc on. Sure it might not seem like much of a difference now, but I don’t see that strategy as exactly promoting innovation. If you could buy OSX separately I might have switched a long time ago. I mean I know apple builds nice machines but to me its about choice too.

  24. @Motorcycle Guy – good point, but that’s their whole business model. Apple is in the hardware business not software. Just look at their current product lineup.

  25. Stumbled across this page on some random surfing. As a Mac user since 1990 and an IT professional in a Windows shop, I get to see both sides of the coin. I actually use Ubuntu as my desktop machine at work and run VMWare for Windows needs. That said, Linux is NOT a ‘pleasurable’ experience as a desktop environment, unless you actually feel more comfortable at the command line. It should at least WARN you the first time it breaks half of your apps because you clicked the ‘Updates are ready’ button. Then I found PC-BSD. It’s kind of the Ubnuntu equivalent of BSD. And if you are used to the Mac command line, BSD is of course more comfortable. It installs software in packages much like the OS X “.app” containers. Storage is soooo cheap and large these days that I don’t care if 10 different programs that use the same lib file each have their own copy, it’s not going to amount to much wasted space. This way, new versions of programs don’t break other programs, and updates to your OS have less impact when the distro maintainers decide to update versions of these files in the OS. Check it out .

  26. Hi Tom, et al,

    I was just surfing by. The article and conversation that follows was a good read. Thank you.

    I’ve been in IT since the early 80’s and a PC user all these years. Though I can’t drop MS altogether due to my skill set, and the requirements of food, clothing and shelter; I find myself more & more disillusioned with the computing world Microsoft has wrought upon us.

    At it’s beginning as an underdog to IBM’s incompetence, to breaking Novell’s stranglehold in PC networking, it was a pleasure to watch it grow. Somewhere along the line, alarm bells started to go off, as MS became a juggernaut more interested in crushing innovation than bringing it about.

    Aside from the convoluted underpinnings of the Windows franchise, the DRM initiative in Vista, which only benefits MS and the media conglomerates is the final straw for me. I don’t like the world MS has fashioned and I’ll be voting with my wallet shortly.

    I’m on the fence between Ubuntu and Mac, leaning towards Mac due to applications. Oh, I’ll still use MS cruft as I still make a living wallowing in it, but the winds of change are coming. What Gates evangelized, to bring legions of corporate minions to his side, Ballmer’s bug-eyed rants and collusion will destroy.

    I hope Apple continues to innovate, as it had to, in order to stay alive. My concern is for the future and vendor lock-in (and the only reason for my fence-sitting). Microsoft too, had a better take on things than IBM or Novell, yet the current OS and application stranglehold it has world-wide, feels no less a burden these days.

    The ray of hope I see is Steve’s rally-cry against DRM (while still providing it), and the move away from a dead-end processor to Intel. I’d feel better if Apple embraced AMD as a second-source to Intel in its hardware designs. Intel’s self-absorbed malaise went nowhere in the last decade, until AMD provided a wake-up call.

    It’s all about choice, competition, and innovation. If Apple embraces alternate vendors (AMD), and drops AT&T as a single-source provider for the iPhone, it may find a watershed moment when all of us fence-sitting minions of Microsoft move towards the light.

    Thanks again for the article… best of luck.


  27. I bought my first home computer in 1999 – a slot loading blueberry imac – which can still run OS9 and the OSx beta on a partition due to some date fiddling – so mac for 11 years at home but I am approaching my 3rd hard drive crash on my aluminium 20inch intel imac 1997 – vista runs beautifully on my boot camp partition – I don't know I love the mac OS always have but 3 broken hard drives in 10 years? is that good or bad?

    1. Alan – not sure what the issue may be there. I'm not sure on the average lifespan of a hard drive, but yours are lasting a bit over three years. I usually put a backup plan into action from day one assuming my drive will crash at some point. What are the variables here? Same brand of hard drive? model?

  28. Hi thanks for the nice blog, i stumbled upon it while random surfing. I just bought the MacBook Pro yesterday and first thing i did in it was installing vmware fusion so i can continue my .Net development to feed myself. I am able to run VS 2008 without glitch in mac using vmware fusion, my 90% requirement out of my PC is solved.
    I am still on my way of getting handy with this sleek new toy, yet powerful. I should say I am loving it. I am not yet regretting after spending twice as much as I could have for little less powerful machine though. My one is i5 processor for 2200 $, I would have got i7 with highest configuration possible if i have brought any generic laptop with win 7. Call me mad, but yeah i am loving it ๐Ÿ™‚

  29. Hi thanks for the nice blog, i stumbled upon it while random surfing. I just bought the MacBook Pro yesterday and first thing i did in it was installing vmware fusion so i can continue my .Net development to feed myself. I am able to run VS 2008 without glitch in mac using vmware fusion, my 90% requirement out of my PC is solved.
    I am still on my way of getting handy with this sleek new toy, yet powerful. I should say I am loving it. I am not yet regretting after spending twice as much as I could have for little less powerful machine though. My one is i5 processor for 2200 $, I would have got i7 with highest configuration possible if i have brought any generic laptop with win 7. Call me mad, but yeah i am loving it ๐Ÿ™‚

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