IRL, I agree with shadowferret, it is an annoying thing most people say to sound smart. The following response has specifically to do with writing (which is what I thought we were talking about since we're in the AW forums):
Overused, yes, like any cliche.
But I do think there's some sense to it, applied correctly. Like jj said, if you ask whether or not you should outline your novel, you'll get another one of those God-awful long-winded debates here. Why? Because the method used would be relative to the mindset of the person using it. There aren't many absolutes in this kind of writing, despite the forum's title name.
Why do we have these long debates over and over? Because the people arguing have used their particular method and they're thinking "What is this wanker saying, my method works! I've seen it work! What they do could never possibly work (because it wouldn't work for me)!"
It's easy to say it's all relative or it depends, but it's equally easy to say my method fits all sizes. I've seen both used fairly liberally, honestly. I prefer the "what works works" clause over anything too restricting. At least with the former someone will try more solutions, and at least learn what doesn't work for them through experience.
As I said, I really think the best way to gauge your situation is for someone to see the actual writing (maybe this is what show don't tell should mean). Otherwise, at least a few of us will give you the "one size doesn't fit all" response. We'll try to help, too, but acknowledging this fact as a caveat isn't insane or annoying. Especially to new members who may not have considered they have their own individual path to follow--in a place where writing advice is rampant and varied, it is easy to get wrapped up in the opinions of others.
I do understand that these kinds of vagueries appear here often, and seem like a lazy response. But sometimes they're the most honest, in threads where at least one person will post their opinion like gospel.