I went with a general "TODO list" first, not just bookmarks. Then I allowed "sending" to other people that use the service. Then I'm going to let people send items by email to those that don't use the service.

Many of my TODO items on H! are private and not published like other bookmarking (delicious) or mini-blogging (twitter) services. When I want to share on my H! mini-blog (like after I read an article) I just click publish and it's put up for the Internet to see.

I'm really scratching my own itch here, and my main thing is prioritization. I find at least a dozen things a day I want to check out, I just don't have time *right then*. Some items are articles I find on news sites, other items are links that people send me. Some are albums or movies I see somewhere and want to check out later. H! lets me keep them all together and once I've checked them out I can do something with them: publish on my mini-blog and comment on, send to a friend, bookmark permanently, etc.

I'd like H! be in the middle of people's workflow for managing items to check out later. I could even make an API for both incoming and outgoing parts of the workflow.

Google Toolbar has an email this page feature
There are dead-simple delicious extensions like http://www.monsur.com/projects/readeroo/

Tumblr makes for a very quick bookmarking service as well http://engtech.tumblr.com

People use TwitThis to bookmark links to twitter all the time

My guess is the value add from HeadsUp is that the people you're sending links to don't have to use the service as well? If they do, then how does it differentiate itself from this stupidly crowded social bookmarking niche?

But "preventing the user from hanging themselves" in this case might result in more complicated code for me and more complicated usability for people. Too much hand holding in the usability and not enough flexibility. It's about balancing all of those things.

I see tagging as being as complicated as people want it to be. Done liberally, tagging can be really simple and useful. As a developer I can only give the people freedom to tag things -- I can't prevent people from going nuts with it.

Interesting discussion though. You could also look at what delicious did with hierarchies. I'm not sure exactly how it works, but I know I've seen some hierarchical-looking tags there.

Ryan, said: "it's not my job to prevent them from hanging themselves."

First, I think that one of the great things about really well designed software is that is *does* prevent you from hanging yourself. Think of Perl and "there's more than one way to do it", vs. the Python philosophy. Precisely the reason a lot of people don't like Perl is because it's so easy to write completely unmaintainable code.

But even if you disagree with that philosophy, another thing to consider is that no feature comes for free. You're not just giving the users an extra bit of functionality, you're also making your application more complicated -- both for you to maintain, and for people to use.

1. English is vague. There are lots of synonyms, like "Capri". The only way to tell is by context and trying to automate that in any way is a really really hard problem I'm not very interested in solving.

My solution is to let individuals manage their taxonomies and use words in whatever context *they* choose. This doesn't mix well with other people's taxonomies though because the contexts are different, which leads to number...

2. Combining taxonomies automatically. I'm not sure people need a lot of recommendations or a lot of choice. Sometimes that can be annoying, you know?

I have my own way of organizing my stuff, why do I care how others do it unless it's going to save me time somehow? I'm not convinced there's a benefit to sharing a lot of taxonomy data between users. Each user has a different agenda and different subject domains they are interested in.

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Bradley, you used an interesting word: "tagosphere". I don't see tags like that at all. I see them as highly personal, not selfish. Everyone has their own tagging system in their head -- and they use it to organize their stuff with tags online. A combined "tagosphere" would be a huge mix of subject domains and context -- a huge mess.

If I want to start a new website, and it services a niche but only has 500 users, why should the tags and taggings from sites like delicious and flickr be locked up there? If by analyzing the tags on delicious and flickr I know that there is a common relationship between Capri and "Ford" or "Island" or "Pants" and a personal relationship between the tagger and their dog, when they tag Capri, it can make the best guess and say "do you mean your dog?".

That's when the value of a system like this really starts to have an impact, doesn't it?

But, sadly, my niche site doesn't get that value when the first person visits and tags something. Why not? Other people have added tags to the "tagosphere". I have added tags to other sites. Inferences could be made...it's just that our data is locked up. (Hmmm...okay, some OpenID stuff may be needed...)

Maybe a lot of this already exists...I have no idea...I'm not as up on things as I should be...

When everyone has their own tag hierarchy, they can decide where to put the 'Capri' tag.

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engtech said: "...if you use your tags as categories you’ll eventually have a right old mess."

I'm not sure I agree with that statement. My Gmail labels do a great job categorizing my mail, I'd just like to put them in a hierarchy because it would be even better. Besides, since each user has their own taxonomy it's their own mess to deal with. I'm not trying to impose my site's tag hierarchy on anyone else.

But you have a point about going too far: people can go overboard with tags and that's up to them. I'm just giving them the rope -- it's not my job to prevent them from hanging themselves. Wordpress probably thinks the same thing.

From the "end user" perspective those words are so close they are almost synonyms: tags, categories, labels, folders. They all do pretty much the same thing. I'm not sure semantics and exact definitions will help the situation, people will do what they want with them. :)

Your sock analogy: you could have 'categories' for sock color, size, warmth, material. If you put the socks in real physical drawers, you'd have to pick one of those categories to organize by. If we're dealing with virtual things we can use all of the categories and decide when we list them which sorting category we want to group by.

As for the Gmail thing: it's a nice hack! But it's probably just OR'ing them together. Can I do more than 2 levels?

An arbitrary set of categorizations speaks of the relationships between items. It can tell me if a particular tag "capri" refers to a car, the island or a pair of pants. How does making this semantic information or context results in a "right old mess"?

If I tag a tag with a number of GUIDs that allow me to quickly refer to, assemble and dissemble an arbitrary number of hierarchical categorizations and relationships, how has this resulted in something worse?

A political-level categorization of Toronto may identify it as a city in Upper Canada, a British Colony prior to 1867 and as a city in the province of Ontario, in the country of Canada, a member of the British Commonwealth after 1867. The context is important...and tags and arbitrary categorizations can help us navigate it.

"Categorizing is like taking all of your socks and putting them into drawers based on colours. Tagging is like sewing a little label on your socks that says when you bought them, how to wash them, and “if lost please return to the dude with the fat cat.” Categories add organization and tags add semantic information. A category can be a tag, but if you use your tags as categories you’ll eventually have a right old mess."

http://internetducttape.com/2007/07/20/climbing-out-of-category-hell/

There's also a script to add hierarchies to Gmail labels:
http://www.arend-von-reinersdorff.com/folders4gmail/