Word choice is an eternal problem for me. If I try to write naturally, I tend to overuse certain words, phrases, cliches, whatever endlessly. Currently, I usually just try to slam everything onto paper (...or computer, or iphone) as fast as I can, then go through and tweak stuff until it sounds right. Often this still isn't satisfactory though, and I have scrapped more stories because I was unable to express what I desired than I care to think about. But, like many weaknesses, I wonder if this could potentially be spun into an asset or strength.
I think, just like many artistic pursuits, we tend to assume that the greats never had to put effort in to get where they are. We assume Newton instantly grasped the idea of calculus; we look at Shakespeare's sonnets and assume he just spouted them off on his first try, fully formed. Of course, there probably were people this was accurate for. We know Mozart was performing and composing before he was ten, and we shoot ourselves in the foot believing we are failures for not being this sort of prodigy. All we have to do is take a look at Honoré de Balzac's life to see this is not true for everyone. One of the greats of French literature, Balzac was renowned for tweaking, and re-tweaking and stressing and obsessing over each word or turn of phrase. The more contemporarily famous Hunter S. Thompson is also well-known for diligently copying out "The Great Gatsby" on his typewriter in an attempt to better understand what made his idols' writing so alluring. It is clear that, for many people, a little discipline can go a long way toward expressing yourself in a way that you can actually be proud of.
That still doesn't really help with the frustration levels though. Breaking your back to reach your ideal can be a major demotivating factor, and seems to be a major reason people I have encountered have abandoned otherwise promising pursuits. In the interest of trying to combat both ennui from repeatedly struggling with the same issues and frustration at not being "naturally" talented enough to output a satisfactory work, I have been trying various methods of writing that seem interesting and also give me a chance to try different combinations of words. The first thing I have tried is branching out in form and genre. I typically write mainly from the first-person, for instance, and borrow much from experiences in my own life or stories told to me from friends or acquaintances. Writing a screenplay (one of my current projects, talked about in a previous post) and working on an episodic work (in the vein of Dickens or the old Japanese novelists) have given me new avenues to explore language and how language interacts with itself. This seems especially true in my current episodic work that follows a single character across multiple generations. By branching out from only things relevant to my own life, I get a chance to break free of the constraints of my personal usage of language and a chance to explore how others would talk or think or feel. I have also begun writing some science fiction (heavily influenced by the Divine Philip K. Dick himself) just to have the opportunity to write different kinds of stories than would be possible in a realistic setting. It is surprising how difficult this can be when not used to it, but I have found it incredibly enlightening to fully form a world of characters free from the constraints of current technology or social norms.
It all boils down to trying to keep interest, and trying not to become too frustrated, while still producing work at a constant rate. No one wants to burn out since very little is as devastating as learning to hate the thing you once loved. If you find yourself stuck, try a different angle. If you find yourself being too heavily self-critical, do something completely outside your comfort zone. It might feel weird at first, but the odds are good, if you are anything like me, that you'll find yourself pleased with your new-found freedom.