My motivation was to get some more insight regarding the never-ending static vs. dynamic typing debate. So, this morning I wrote a Java program (the standard arithmetic expressions parser/evaluator) and then I tried to write it in Ruby. Unlike previous occasions I actually took the time and searched the web for a real Ruby IDE. After a few disappointments (#1, #2 and #3 - it was on my Windows machine, maybe they work better w/ Linux) I settled on NetBeans.
My Ruby skills felt somewhat rusty so I decided to warm-up by TDDing an easy kata. After the third or fourth test case I noticed a very funny thing: Ruby was much easier than I remembered. Suddenly I didn't feel so rusty. Thinking about it I realized that this was not due to the language but rather due to the IDE. In all past attempts I was too lazy to install an IDE so my Ruby experience was always through a text editor and a command prompt. Once I had an IDE at my disposal (and I mean a serious IDE: completion, go to declaration, templates, the works) the learning curve has flattened.
For example, I wasn't falling back to Java's curly braces as much as I used to in the past, because pairs of def/end keywords were being injected by the IDE as I was typing; Fixing the (highly non-friendly) syntax error: "unexpected $end, expecting kEND" was much less painful since I had this nice red thingy on the editor's side bar; Determining whether an expression such as assert_equal(0, x.get_result) can also be written as assert_equal 0, x.get_result was a breeze.
The morale here is two fold. First, there is the trivial issue of WYSIWYG tools making it possible even for a complete beginner to get things done. Second, you can't really evaluate a language without an IDE. When you evaluate a language you are unconsciously comparing it against your programming experience with your current, favorite, language. For sure, you have all the tooling support you need for your current language, so unless you get some tooling support for the new language, the comparison is unfair. Once you set up an IDE for the new language your programming experience will (dramatically) improve.
I guess there is a deep psychological issue here. We are humans. We always try to do as little work as possible. When we try a new language we tend to download the least amount of tools. We rationalize it by saying something like: "well I am a seasoned programmer. I don't need an IDE/Debugger/whatever to get the feeling of the language". This is a risky -- and usually a plain wrong -- assumption.