I don't want to turn Hubski into 4chan, although I do like the idea of feeling comfortable with posting certain things anonymously. This is one of the reasons people make throwaways on reddit. I also think it's great to be able to use a site without even having to register, but if you guys don't like that, it could just be made that you still have to register to post at all, but you have the option of posting anonymously. If you guys still feel uneasy about this, maybe it could be made that you can only post anonymously if you have a certain amount of badges, or you have to use a badge to make an anonymous post.
I think that anonymous posting would ruin the integrity of the site. There's something to be said about being conscious and accountable for what we say on the internet. I've only been on Hubski for a couple of days, but I feel as though the people here value truth, honesty and maybe even a bit of humility. Sometimes we can lose ourselves in the anonymity of the internet, we forget about the other person on the other side of the screen, we tend to see those people for the words and letters they use rather than the humans they actually are. I don't want to be 'that girl' but I think anon posting here on Hubski would take it down the rabbit hole that Reddit and 4chan have become. That, I believe, isn't the Hubski model.. Hubski is different, and that's what drew me in.
Why not just make a throwaway to post the things that you'd like to keep anonymous? Maybe there could be an anonymous tag where anyone in the discussion can choose to be anonymous or not.