The idea that people won’t pay for content online has become such a part of the Web orthodoxy that New York Times Executive Editor Bill Keller risked getting lynched earlier this month for merely musing about paid models for the online editions of his paper. Not helping Keller’s cogitation was a contemporaneous “secret memo” from Steve Brill and a Time article by Walter Isaacson, both which advocated variations on the micropayment model. Neither advances the topic much beyond what most Web entrepreneurs understood long ago…
via Not all information wants to be free. – By Jack Shafer – Slate Magazine.

A good review of what works and doesn’t work with paid-for content and some of the problems that the publishing world is currently facing. Whilst the article doesn’t cover all the possible attributes of successful paid-for content services, Shafer does provide a fairly comprehensive summary that covers most aspects, as follows:

Not all successful paid sites are alike, but they all share at least one of these attributes:
1) They are so amazing as to be irreplaceable
2) They are beautifully designed and executed and extremely easy to use
3) They are stupendously authoritative

Sites that immediately spring to mind that fulfil some of these attributes are:
Flickr, Wall Street Journal, Financial Times and McKinsey, together with a plethora of B2B titles.

However, in the article Shafer wonders why people use iTunes and similar services “when they could easily download the band’s entire discography via Bittorrent for free”, and speculates whether it is because it is an outside-browser-experience. Whilst this may be a factor, there might be simpler answer which could be added as a sub clause to number 2) in the list above, namely:

2a) Sites that take the effort out of doing something that can be done for free (legally or not) but is time consuming or requires a small amount of additional technical knowledge.

In the case of iTunes, it also shouldn’t be forgotten the incredible power of marketing to support the service, the integration of iTunes into their hardware products and the brand alligence that Apple customers exude – an additional consideration to any business considering introducing a paid-for service.

UPDATE, 23/02/2009 >> Two pieces in today’s Media Guardian this topic and how it relates to newspapers:
Jeff Jarvis, News sites should quit moaning about payment and just gopher it
Jemima Kiss, The writing on the paywall