I wonder how hard it would be to make the jump from C++ to Python and/or Ruby on Rails.
You’ll get the basics quickly enough, but extensive C++ experience actively inhibits your ability to think in terms of dynamic OO as used in Ruby or even Python. The way you should think about “good” design is just that different. No matter what subset of C++ you’re used to (nobody uses the entirety; perhaps a few dozen people in the history of the language have fully understood the entirety), you’re used to playing by some fairly strictly-enforced, static rules about construction that simply don’t apply in the New Order of Things.
Obvious example: classes and interfaces. In C++, you define interfaces through classes with virtual (usually pure virtual) methods that you then implement in (often multiply-inherited) subclasses. Ruby, done properly, is different; there’s no equivalent, really, to C++’s pure virtual methods (thank
$DEITY); “duck typing” a) makes the “contract” between components much more casually fungible and b) encourages smaller, more atomic classes than you’d typically write in C++. It sounds simple and straightforward, and it is and you think you know all about it — until you’re a few years in and the light bulb finally flips on.
(source: 15+ years coding C++ on a daily basis, and coming up on 5 total years of equivalent Ruby and 2 years of Python experience.)
YMMV. TIKOAR. IANALNDIPOOTV. LSMFT. And, for you Singaporeans, as always, terms and conditions apply*.