I missed commenting on this earlier:
... why are creative works and acts so often frustrating, feeling like a trap? Why do we worry over writer’s block, argue about subjective artistic choices, or turn creative work into a death march? That’s because the sheer opportunity of creativity and all the options leads us to make bad choices.
Steve goes on to enumerate several ways we make bad choices: creative paralysis (too many choices, not enough power to choose); fear (second-guessing everything); miscommunication (putting the audience last because you have some unexamined contempt for putting it not-last); and safety (doing what you know works, for the 361st time).
Of all these, I want to concentrate on creative paralysis first, because it seems like the dilemma I hear about the most. I may circle back to the others in time, but this one stood out especially firmly when I read Steve's post.
Some of you reading this might be familiar with the "toothpaste paradox". If you go shopping and you see 40 varieties of toothpaste, and you have no idea how to distinguish one from the other in a meaningful way, you just stare at the shelves in front of you for minutes on end and have no idea what to do next. If you're me, you just grab the tube that's at chest height and get the hell out of there, because most commercial toothpastes are not all that different anyway, and who wants to spend that much time figuring out something so ultimately trivial?
Now, a short exercise. Go back and re-read that last graf. Try to find the one phrase in it that would break the deadlock.
The phrase you're looking for is how to distinguish one from the other in a meaningful way. In other words, if you have no good criteria for how to pick a toothpaste, you'll be stuck even if you only have two varieties to choose from. If you know exactly what you want, or at least how to narrow down the choices, you spend less time being indecisive.
Back to the main subject, creativity.
/r/python subreddit, you see a great many posts from people asking one variation or another of the same question: What should I work on? They want to create something with their programming skills, but they can't choose, and so they founder and look for someone else to tell them what to do. (Never a good idea in the long run.)
The best answer I've seen to that question is some variation on the following: Pick some problem that's personally relevant to you and solve that. That provides a criterion — personal relevance — by which they can screen out a lot of missteps and false starts. They usually also get recommended the book Automate The Boring Stuff With Python, a great resource for seeing firsthand how to do exactly that.
Programming is by no means the only venue where people ask such a question. "What should I work on?" is all too common a dilemma with other creatives. And it is typically the first half of some line of thought, the other half of which could be something like one of the following:
All of these, especially the last one, seem like symptoms of someone who hasn't yet developed a proper set of criteria for developing their personal work.
This is much harder than it seems, for a reason that eluded me for a fairly long time: Personal preferences aren't the same thing as filtering criteria. In other words, just because you like to write about X doesn't mean you've therefore figured out that you're going to write about X. It's a good starting point, but it's only one of several stackable filters you can employ.
I keep a wiki in which I place all manner of story ideas. Some are nothing more than stubs of a few words that would only make sense to me and no one else ("what if Batman, but time travel"*). Others are more heavily developed, either because I wrote down a great deal in one sitting or because I've been adding incrementally to the entry over a long period of time. But just because something is in there doesn't mean it's automatically going to be a project. There's a number of internal thresholds that a project has to cross for me before I can even consider working on it:
There's others, which I won't enumerate here, but you get the idea. The bar is set deliberately high, but at the same time I'm constantly sending things out to try and hurdle over it. Instead of just sitting there surrounded by too many ideas and dithering between them, I try to find ways to constantly put those ideas to the test, and to bring new ideas into the fold for testing. That way, it becomes less about being overwhelmed with possible choices, and more about refining the ways to choose in the first place.
I'm going to talk more about the above four points in a future post.
* Arbitrary example. Do not attempt.
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