I drafted this post quite a while ago, but felt it was important to finally put it up.
Ok, so I think almost every fanfic writer I've ever interacted with or read anything from has times of insecurity or feeling inadequate about their writing. We've all written something and been less than proud of it, or gone back to old stories and wondered how we could possibly have ever written something so terrible. Or we'll read something from another author and think, wow, my work is so vastly inferior to this that I should just quit writing right this minute and never return because I can't possibly compare to that. This happens to most of us. Seriously, probably even that person whose writing you think is on a level you could never comprehend. Yes, that one. The good news is that it can often help us with our desire to learn and grow as writers. But there can be a downside to that as well.
Now, here is one thing I've seen, and been guilty of myself, and it is to announce either in a summary or an author's note that your story isn't very good. Don't do that! How does that inspire anyone to read your story? Let the reader decide whether they like it or not, don't decide that for them. If they don't like it, that's their decision, and hopefully they just keep it to themselves and move on and read something else. But hey, maybe someone out there might like it!
Which brings me to another point. By saying that your story is terrible, you're kind of insulting anyone out there who might have read it and liked it. Look, I myself have stories of mine that I'm not that proud of. The ones I wrote a long time ago, the ones that I'd probably do a George Lucas Special Edition on if I had the patience or desire. I cringe at some characterizations or scenes that I've written. But the thing is, someone out there liked every single one of them. I will still get a new favorite here or there or maybe even a review. And yes, part of me kind of cringes like, wow, you liked THAT one? But the thing about fanfic is that there is something for everyone. And at the time I wrote some of those stories, they were the kind of stories I wanted to see, and clearly someone else was interested enough to read them too. So why should I tell them my story is terrible and make them feel bad about liking it?
Another big problem with bashing your own writing is that someone somewhere has probably read what you've written and not only really likes it, but compares their own writing to it. They see what you wrote, and think, well, I could never write something that good. So then how do you suppose that person feels if not only do they already think your writing is way better than yours, but then they see that you are telling them that it is terrible? At that point that person probably wouldn't dream of trying to publish something if they think your writing is vastly superior to theirs, and you're now telling them that your writing is terrible. So how bad must their stuff be if you are calling your own writing terrible? I think it only serves to further discourage people who were already worried about posting.
I get it, and like I said, I'm guilty of it as well. I know we all like to come across as humble and to not toot our own horns. That's ok, too, I'm not saying any of us have to walk around touting our writing as the next Shakespeare or JK Rowling. I'm just saying that we aren't doing ourselves or anyone else any favors when we walk around trying to convince everyone that our writing is crappy, or inferior to anyone else's. We're all different writers, and that is part of what makes it all more interesting. How boring would it be if we all wrote the same or could be easily ranked from best to worst? And why should anyone even be considered the best or the worst? It's all subjective, and there is room for all of us. Don't compare yourself to others, don't apologize for your own writing or tell people it's terrible. Nobody is obligated to read what you've written, just put it out there and let the reader decide what they think of it.
Keep in mind that most of your thoughts of inadequacy have been felt by every other writer who has ever posted a story around here. Most of us have the same anxieties and worries that our writing isn't as good as that person's, or this person's, or just good enough in general. Or that our story is boring or that nobody will want to read it, or that people will judge us as humans because we can't know what we're talking about because we've never experienced something we're writing about. It doesn't matter. We're all just writing, trying to come up with good stories and do the best we can. Don't stress about it, and don't make a habit of disparaging your own writing because more often than not you're not even just hurting yourself by saying these things, you're hurting others.
I realize some people may disagree, or feel like how other people feel about their own writing or inadequacy isn't your responsibility. And you're right to a point. The thing about fanfic writing though to me is that more than anything, it is a community. And it doesn't really work well if there isn't some community aspect to it. I mean, think about it: would it be anywhere near as fun or interesting if only one person wrote stories? Even if they were all fantastic stories, it's still fun to read things from lots of different people. And we can always use new writers, so it's important to create as encouraging an environment as possible to get more people to start writing and sharing their stuff. You never know where the next great story will come from, or what stories we've missed out on because someone felt like they weren't good enough to write or post.