I have been asked this before and I always give the same advise. It is sometimes not well received, but it works quite well and has helped migrate about 20 or so people that I personally know over.
Make a list of applications
Make a list of applications that you use on a daily basis. Try to list everything. If you use notepad, then list notepad. Assume nothing. When I went from mac to ubuntu this last time, I made the list. So for example:
- Sublime Text
- git tower (and soon).
The leap of faith
Next, using either a totally new hard drive, and removing your windows/mac one (if you can afford it), or by totally erasing windows (can't erase mac because of the hardware issues), Install Ubuntu. Do NOT DUAL BOOT. People who dual boot, in my experience, just end up booting to windows when they get lost instead of educating your self. By having the second hard drive you have an option, but your naturally inclined to try to find a solution in Linux first. Again IMO, don't dual boot. Install Ubuntu only.
OMG What have I done
Be prepared for some down time. Linux is actually much easier to use then windows. However, there is a period of adjustment where you still try to do things the windows way. Like spending time looking for a "start menu" when you just use the dash in Unity. This is even more true on some smaller issues. For example, "How do I copy and paste?". There are three clipboards in Linux (though people usually only use 2 of them). Getting your head around those types of changes can be tricky. Just persist, and power through it. Once you get over "the start menu should be in the bottom left" phase, everything goes lightning smooth.
So having a Ubuntu computer that you can't do with what you want to do, is about as useful as a pen without ink. Take your application list and start looking for alternatives. Most applications will have either Linux versions or alternatives. Some will not. For example:
- Sublime Text 2 - Linux Native version
- Transmit - No alternative though filezilla does what little I used transmit for
- Chrome - Linux version
- Git Tower - Smartgit
With each application you have to remember that you need to shed your perceptions of how things should work. Again this will bring another phase of confusion and frustration, but it will pass quickly. In truth you will likely find that only one or two of your "core" applications have problems "translating".
Run Virtual box, install windows, and install only those applications that you can't find workable replacements for. This is a concession to the real world. You should use it as little as possible, but if your business runs on QuickBooks, then nothing but QuickBooks is going to work. However you should really try to find working replacements.
Books are nice but the Linux world changes too fast. Use Linux, ditch the books. Keep a list of good sites like AskUbuntu, and any other sites that have documentation that you find useful. After a very short time you will find that you just reference them.
Real World Transitions
Like I said, I have used this method to help about 20 or so people that I know in real life (not the internet) make the transition. The time to feeling comfortable varies. My Grandmother felt comfortable in about 2 weeks, though her applications where standard browsing, Open Office, and a special piece of software for dictation. An IT Manager I helped took a couple of months, but there was a lot of specialized hardware and software that was involved. Most people take about a month to feel comfortable and about a year to
feel like they have mastered their machine. If your doing this in your business or on a work machine expect about a 3 days of total down time in a two week period, 80% less productivity in the first week, 50% or so the second, then things returning to 0% or less in the following weeks. Of course this depends a lot on what special hardware/software you use and how fast you learn new things.