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A long-time Windows user hears about how great Ubuntu is, downloads the ISO, burns it to CD, installs Ubuntu, tries to use it, finds the hardware isn’t configured properly and the applications she needs don’t work on Ubuntu. She gives up and leaves (or attacks Ubuntu as being “not ready for the desktop” then gives up and leaves).
Were she and Ubuntu just never meant to be together? Possibly. But at least one problem may have been the migration strategy she and hundreds (if not thousands) of frustrated potential users have—dive right in!
While I acknowledge that the dive-right-in strategy may work for some people, I don’t think it’s the best one for most potential Ubuntu users (potential ex-Windows users) to adopt. Here’s another approach:

How to migrate from Windows to Ubuntu

Examine your motives. Ask yourself why you want to migrate. Is it out of curiosity? Do you want a free version of Windows? Do you want to try something different? Generally, the most successful migrations usually do not expect Ubuntu to be a drop-in Windows replacement and recognize that a little bit of culture shock and learning may occur during the transition.
Take it slow. It’s quite possible that you may migrate slowly over a few months or even years and then regret taking it slow (If only I’d just installed Ubuntu and started using it right away…), but, really, what’s so bad about that? It’s a lot worse to accidentally delete your Windows installation, realize Ubuntu’s programs don’t suit your computing needs, and wish you’d just stayed with Windows.
Start with open source Windows applications. As a practical extension of the take-it-slow philosophy, don’t even bother with Ubuntu just yet. Ubuntu won’t run all Windows software, and so you’d better see if you like the kind of software that is made with the same Free/open source philosophy that Ubuntu is made with. Switch from Internet Explorer to Firefox. Try OpenOffice instead of Microsoft Office. Use GIMP instead of Photoshop. Test out Audacity, Inkscape, and Frostwire. You can find a more complete list of open source Windows applications at www.opensourcewindows.org .
Get to know the live CD. Once you’ve gotten used to using open source applications in Windows (and supposing you have 256 MB of RAM or more—I’d recommend 512 MB), download and burn the Ubuntu CD and play around with the live CD. The live CD allows you to use a fully functional Ubuntu operating system without affecting your hard drive (it works off the CD itself and your computer’s memory). The live CD has two major benefits for you at this point. It allows you to try out Ubuntu in a noncommital way, and it allows you to get a preview of any hardware recognition problems you might run into (and have to fix) should you later decide to install Ubuntu. I’d say you should play around with the live CD for two to four weeks, if not longer.
Consider Waiting to Purchase New Hardware. If you have a difficult ATI card, broadcom wifi, and a Lexmark printer, your Ubuntu experience may not be that pleasant. You’ll have to spend a lot of time working the command-line to get certain hardware components working properly. You may decide you want to roll up your sleeves and go for it. But I think it’d be best to stay with Windows, and if you are still interested in Ubuntu in a few years, buy Linux-compatible hardware or buy a Ubuntu-preinstalled computer.
Set up a dual-boot. If you don’t want to wait on getting compatible hardware or if you aleady have compatible hardware, go ahead and set up a dual-boot with Windows. That way, you’ll be able to customize Ubuntu (the live CD settings don’t get saved) and run it at native speeds (the live CD runs more slowly than a full installation), but you’ll also have access to Windows if you need to run back to the safety of familiarity. The Ubuntu installer is fairly user-friendly, but if you’re still scared of messing around with partitions and boot loaders, there’s a project called Wubi that allows you to install Ubuntu from within Windows. It sets up Ubuntu as a removable application in Windows and uses Windows’ boot loader to pick which operating system to boot into.
Set aside some time. If you’re one of those “time is money” people who would rather pay for a translator than learn a new language and would rather eat out than cook yourself, then don’t bother migrating. Even if you buy Ubuntu preinstalled, the Linux desktop experience is so radically different from Windows that there will necessarily be a learning curve (yes, even if you don’t have to configure hardware and even if you don’t have to use the terminal). Software installation is different (some would argue that it’s better). Theming is different. Updates operate differently. The user interface is different. The culture of the community (if you choose to get involved with it) is different.
Enjoy the move. If you’ve gone through all these steps in this order, you’re likely going to end up a happy Ubuntu user. If you got stopped at one step along the way, at least you didn’t invest too much time in a futile (and failed) migration.

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