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I can think of two good reasons to keep a URL short:
1. A long URL may be broken in an email.
2. Search engines may dislike a long URL.
On the other hand there may be some fairly good reasons for some URL's to grow rather long even if you create them manually.
I am in the proces of rebuilding a 100+ page website with a rather complicated structure, and I try to give all directories and files names, that actually show what they are about.
For one page this results in a URL with about 100 characters. I fear that this length may create some problems and it would be better to either shorten some directory names or change the directory structure so that some pages are moved nearer to root level.
How do other members deal with such problems? Have you set a maximum for the URL length that you allow yourself?
I try to give all directories and files names, that actually show what they are about
This is an important question, and loaded with shades of gray and trade-off decisions. It involves both Information Architecture, the directory structure and the navigational structure - and these are not the same thing.
First, I've backed off my previously extreme concern about keywords in the URL. Yes, they can be a minor help on some search engines. But look at this very site, webmasterworld.com, as an example of succes in the SERPs without that factor at all.
So while I do use some keywords for page names and directory names, I don't worry about having the URL deliver the same clarity of description that, say, a title or an H1 element would.
Second, the navigational structure does NOT need to mirror the directory structure. Yes, this helps keeps things intuitive on a "macro" level, but again, look right where we're reading to see an excellent counter example. The breadcrumb trail on webmasterworld.com does not mirror the directory structure.
I've got lots more I could say on the topic, and I'll probably chime in again on this thread, but for now Ill make one comment directly about the quote I chose from the original post. It can be helpful to give directories a descriptive name, but HOW MANY directories you create is another question altogether.
What I'm saying is that you do not need one directory for every topic covered - and using an extreme number of directories and subdirectories is one reason for the "too long a URL" result.
Many of them are significantly shorter and they still have the most relevant keywords in them. Keywords that both look nice in a URL in a SERP and make my editing easier.
But there are quite a few directories in root now.
Information Architecture, the directory structure and the navigational structure .... these are not the same thing
I tried to keep these three structures identical because I like structures in different dimensions to support each other. But in the end I decided to make the directory structure largely independent from the others.
This may actually prove to be an advantage because it is now easier to integrate new articles (or rewritten older ones) in the information architecture in a natural way. They do not have to fit into a rather rigid structure, dictated by a directory structure that was sensible two years ago.
But I will have to decide how my sitemaps should be now!
For me it's about focusing on the user experience from every angle, and requiring technology solutions to bend to the user rather than the other way around, as much as is feasible.