Linux

In the beginning it seemed like everything was a task -- how do I install new software, how do I set up the right display or printer driver, how do I upgrade the whole OS? Then it quickly got down to making things look and act in a way that made more sense to me, or even adding and moving things around on the start menu. Back when I started, setting up dual monitors required manually building an X11 startup file and upgrading the OS usually meant compiling a new display driver, but that was around 2005 so of course things are MUCH better now.

Eventually you'll get down to the point of simply finding compatible software to reproduce something you did in Windows, which usually isn't difficult. A lot of this is going to depend on exactly how you use your computer and what you expect from it. I was already using Firefox and Thunderbird when I made the switch so that covered like half the things I needed at the time. Microsoft Office is (thankfully) gone although some parts of Libre Office still feel a bit rough. There's pretty much no remaining support for Adobe pdf files, so if your employer makes use of advanced features for filling out forms then you may run into trouble (of course standard PDFs are very well supported). You will find things along the way where some business has made a point of locking people in to their product and there's not much you can do except point out to your employer that they're buying licenses for something that is free and more widely supported in open source products, but mostly you'll just find your own solutions to work around these issues.