What tags are not.

I got excited about Web2.0 about two years ago; I read an article about flickr, which fawned over its novel photo "tagging" feature. That article speculated that OS's will adopt tagging in place of hierarchical folders.

Here's where I went askew. This article -- or how I read it -- led me to see tagging as a brainstorm-esq -- almost sub-conscious -- process. Ie. for each flickr photo, delicious link, or local file, you were to just spew a series of words (or hyphenated phrases), and in months or years to come, you or any reasonable person would spew a similar set of words when pondering the photo/link/file.

I even developed this into an idea for a service-business: Staples and Grand & Toy have notoriously difficult information architectures -- both in their physical stores and online. How do you categorize whiteboards and CD jewel cases in one dimension? But if a sample of the population assigned 6 intuitive tags to every Staples SKU, eventually, any non-caveman would be able to find stuff with a command-line-style search.

This is all interesting, but the point of this post is that tags should not be spewed in a brainstorm; they should be carefully considered. My delicious account has tags like: business, company, business-idea, start-up, entrepreneur, entrepreneurialism. So I feel forced to re-tag every cool start-up with six tags, where one will do.

No, the right approach to tagging is to assign the right tag in both your brain and the tagging system. Have one word for one underlying concept. Tag-clouds and other nifty features help with this ... you can assign what you have most-often assigned.

Tagging takes discipline. Rather than re-build my delilcious account (and not super-happy with Blink List), I'm going to take the opportunity to start-over with diigo.com, which techcrunch rates well.

Planning travel with the web is so helpful, you can almost skip the trip!

Lonely Planet was, and is, the gold standard for travel books. Want to know a $45 a night hotel in Paris that's safe and clean -- spend $25 on Lonely Planet Paris.

But, frankly, reading such a book is not a very rich experience. You can't really tell if your wife would prefer Paris' Marais district over Saint Germain des pres. And you have no idea whether the information is up to date.

Flickr & Youtube

Today, I still plan travel with a Lonely Planet guide, but I go beyond. The photo management site Flickr, sold as a tool to store and share photos, doubles as tagged photographic evidence of everything on Earth. Want to see an Andalucian Villa? Do a Flickr search. The key I've found is to search for both a place name and an activity. Searching for "paris" is too general. Do "Paris" and "Shopping" or "Seville" and "yelling." If you're going outside the tourist season (when most photos are taken), throw in a month or season name. Before booking a hotel room, search for that ... most often than not, I've found one person has taken the obligatory room and window shots.

Flickr is enjoyed by photo snobs, so there are plenty of beautiful shots. Not so much with youtube. But by searching for videos taken within a town or street -- even if they're of two kids doing skateboard tricks -- instantly immerses you in the overseas environment. Seeing the action can make what is at first foreign come to be natural.

Tripadvisor.com

These guys seemed to get very smart in the past year -- or, like fax machines, they only became useful after they become popular. Either way, it seems that even the most remote hotel is now reviewed by multiple people, with detailed written reviews, a quantitative survey and even, occasioannly, amateur photographs. In many cases, by reading individual reviews, you can reconcile wildly different review scores. For example, one person may give a hotel 5 stars and comment that it was very clean and friendly, while another would give it 2 stars and add that the towels were sub-par and it room service was slow; the first person may have splurged on a rare, nice hotel, whereas the latter may be used to extravagance and found this place lacking.

Expedia also has hotel reviews, and I believe they are tied to actual reservations made through Expedia, so they're much more likely to be authentic -- that said, as a writer, I like to think I can spot a bullshit review.

Booking

Hotels.com and other sites often have very good special prices. They key here is to check every day for weeks in advance of a trip. Furthermore, it's worth it to call the hotel to confirm the reservation within a few hours of making it through one of these sites.

Information

Finally, if I can't find some information anywhere else, I use Yahoo Answers. Here I can post a question and categorize it narrowly -- often, within 2-3 hours I have multiple responses. Typical questions may be: how much is a taxi from XX airport to the centre of town.

Why satellite radio will beat iTunes, IMHO

Regardless of whether Napster was itself illegal, it was only popular because no alternative existed which had the blessing of music "owners." Today, the iTunes store is a very popular web-tool that essentially gives users what Napster did, but with the blessing of the music "owners."

Some people who use iTunes own fewer than 1000 songs. In my opinion, in a library of 1000 songs, about 200 are truly enjoyable. However, a typical core library of 200 songs begins to lose its "freshness" after about three months of rotation. Adding songs to that list through iTunes costs $1 a song, so even being very careful and adding only "core" songs, it will cost $198 to gain another three months of "freshness," or $66 per month. Some people will pay this, and enjoy picking the songs. Many will find the cost -- and agony (watch someone sweat over a large, unfamiliar menu) of making 66 individual choices per month -- prohibitive.

Satellite radio (or Internet radio, TV radio, or other digital audio), on the other hand, can be thought of as someone with a library of 250,000 songs, including every new one. The key advantage, however, is in the feedback. If a satellite radio station can be "trained" to know your musical tastes, then it can not only deliver old songs that you are likely to enjoy, but predict which new songs you will also like. In fact, if it can narrow your tastes well enough, you may even be able to receive just a core of 200 good songs, out of a selection of 250,000 possible songs, and this core will automatically update with newly released songs every day, completely updating before any song becomes stale.

In the case of portable music, an iPod is comparable in price to a satellite receiver (it is likely cheaper, but has a shorter life). However, satellite radio costs close to $15 per month, while 66 new songs per month on iTunes costs $65. Furthermore, for the average consumer, no decision-making is required.

Despite my love of iTunes, I think that, within a decade, music-as-content will be stored on central servers and streamed to users, rather than "owned" by individuals.