The single biggest obstacle in my writing is: Microsoft Word.
Every single time - and I mean that quite literally, every time without fail - I sit down to use this program, at some point it leaves me murderously frustrated.
How is it possible to create a program so unbearably difficult to use? Especially when I am using it for such a simple task.
I get that when I am doing page layout for publishing, things can be twitchy. But simple things, like formatting and styles and tracking changes, should be bullet-proof. At no point should I be able to click a button and wonder "WTF just happened, and how do I make it unhappen?" Especially when it is the same button I've clicked ten times before.
It's just bad design. The entire program reeks of add-ons, tack-ons, and hacks. I would switch to Open Office, but I doubt it is any better. Just one of the ways Microsoft has poisoned the entire industry: their crap is now considered the gold standard.