Yes, languages that are truly dynamic (ships with a REPL, has a instant change->run this snippet workflow, can redefine anything in the runtime AT runtime) does work a lot better than Python which is basically comparing the type systems of Java and Haskell.
Give it a try. Worst that can happen is that you now have tried and learned something different, I'm sure it'll give you some knowledge that'll be helpful in any programming language :)
Pharo is a nice implementation of Smalltalk and they have a nice page that describes the top features of the language. Take a look and see if it's different from the developer experience you had with Objective-C: https://archive.is/uAWX5 (linking to a archive via archive.is as some images couldn't load)
Everything Is An Object in Smalltalk, and of course this can't be true in Objective-C due to its mixed heritage.
I'm, not sure if Smalltalk and Clojure do this better, but since I've gotten into static languages, I basically haven't looked back, and I haven't missed the dynamism much at all.