Music, and singing specifically, is one of my major hobbies, and I am or have been a singer or conductor in countless choirs (okay, not countless, but it's in the dozens). For the past few years, I've been assistant conductor with a local barbershop chorus, and yesterday we had a board meeting. Now, our chorus is mostly old men, and they're getting older every year. Apparently, as the resident "young guy," I'm supposed to help them figure out how to attract new, preferably youthful, members. Here's what I wanted to say at the meeting:
"Right now, most of the chorus treats barbershop as a social club. Rehearsal starts late, once everyone's done having their private conversations, and tends to be interrupted by rambling monologues, including some frankly offensive political and racial 'jokes' (to give you an idea of how clueless some of the older members can be: last year, I had to explain to a group of our singers why it's not appropriate to perform a minstrel song while wearing blackface in our Fall Show. They were not being ironic). It's obvious that most of the chorus members never look at their music outside of practice; we're only able to learn a few new songs a year, despite theoretically logging almost 120 hours of rehearsal over that span. As a result, most of that rehearsal time is dedicated to learning notes and rhythms, and almost no time is left for working on anything that might make us actually, you know, sound good.
"There's absolutely nothing here to draw a new member in. If a potential chorus member came to one of our practices, he'd rightly conclude that there were at least half a dozen local choruses that he could join which would sound better, have more engaging practices (working notes and rhythms is one of the least satisfying uses of practice time), and at which he wouldn't end up spending at least half an hour each week awkwardly standing around listening to octogenarians rambling on about people who died twenty years ago, quartets they heard perform forty years ago, and their own myriad medical conditions."
Obviously, that's not what I said. Instead, I suggested that we try to focus on producing a better sound at our performances, since there's a pretty strong correlation between how good a group sounds and how likely potential singers are to want to join it. While I won't say the suggestion was dismissed entirely, the opinion of several of the board members seems to be that our group already sounds fine, and that we don't need to worry about where we're at musically. After all, at our shows, people always come up and tell us how great we sound. In any case, our group isn't supposed to be an elitist haven for professionals, I was told; to quote: "A lot of the guys here just want to have fun, and besides, audiences can't tell the difference between good singers and okay singers as long as you're having fun on stage."
Singing and writing are similar in a lot of ways: both are intensely personal (your voice, your ideas), both have objective bases (notes and rhythms, grammar and punctuation) upon which are layered more subjective decisions (plot, pacing, characterization; blend, tone quality, inflections). And, in the case of my barbershoppers and those fanfiction writers who put their work on places like FIMFiction, both involve exposing the public to your product.
In fact, the similarities between the barbershop chorus and fanfic writers are pretty significant. Both are composed of a small subgroup who take what they're doing seriously (too seriously, many would say), and a larger core for whom "it's just for fun" is an all-purpose excuse. For members of both groups, it's easy to find folks who'll ladle praise on them, regardless of the actual quality of their work. There are large factions in both groups who seem to believe that putting in effort and having fun are antithetical.
And for both, criticism can be a bitter pill to swallow. The fact that singing and writing are both so personal means that it's easy for criticism to sound like a personal attack. When our chorus last performed at a district convention (where there are professional judges who critique each group), we received pretty low marks. The larger part of the chorus angrily dismissed the judges' complaints, saying things like "We sang those songs the way we wanted to, we don't need a judge to tell us how to sing," or "What they're looking at and what real audiences care about are two different things." And on the fanfiction side... well, I'm sure anyone who's been involved in any fanfic community for any length of time can fill in plenty of stories of hyper-defensive authors by themselves.
Unfortunately, I've never quite developed the knack for helping these people, in music or in fanfiction. You can reach a lot of people by making sure that your comments are neutral in tone (if not in content), by mentioning at least a few positive things, no matter how much you have to reach to find them, by praising improvement, however incremental, and most of all by offering constructive advice with concrete examples. But if someone can't tell the difference between "There are a lot of things you could improve about this song/fic" and "You are a terrible singer/writer" (and there are many people like this), how do you reach them?
Sadly, I don't know.