When talking about how dynamic scripting languages are designed, people have a tendency to divide them into "There is more than one way to do it" and "There is one way to do it". Perl is the quintessential example of "more than one way", and Python is the opposite, going so far as to make it impossible to have your own indentation.
These different ways of doing things really divide programmers. Some hate the way Python gives you a bondage strait jacket and no scissors, while some programmers love that they don't need to make any choices and that everyone's code will be equally readable.
From a pure perspective, the Python philosophy seems to be the right one, but it just doesn't work for me. In the same way, I agree with Perl's way of doing things, but the problems that cause in most Perl code is just amazing. Sometimes it feels like the Python way is actually directly a result of someone reacting extremely badly to a Perl code base and decided to never allow that to happen in Python.
So what's the point? Well, the point is Ruby. In fact, Ruby has almost all of the flexibility of Perl to do things in different ways. But at the end of the day, none of the Perl problems tend to show up. Why is this? And why do I feel so comfortable in Ruby's "There is more than one way to do it" philosophy, while the Perl one scares me?
I think it comes down to language design. The Python approach is impossible for the simple reason that what the language designer chooses is going to be the "one way", by fiat. Some people will agree, and some will not. But what I'm seeing in Ruby is that the many ways have been transformed into idioms and guidelines. There are no hard rules, but the community have evolutionary evolved idioms that work and found out many of the ways that doesn't work. This seems to be the right way - if you do the choice as a language designer, you have actually chosen the people that will use your language: that's going to be the persons who doesn't dislike the language designers choices. But if you leave it open enough for evolutionary community design to happen you can actually get the best of both world: both a best way to do things, and something that works for a much larger percentage of the programmer world.
I have come to believe that this is one of the major reasons that Ruby feels so good to me, and is such a good language. And it's a lesson for language designers. When you choose philosophy, make sure to take the possibility of communities and idiom evolution into account.