> When you're a small startup, what matters is the expressiveness of your language, and the ability do do a lot of things very very quickly. Type safety, performance, readability, those things don't matter. You're just a bunch of engineers who know the whole codebase inside out, you're pretty certain of what you're doing.
I'm not familiar with this use of the term "expressiveness".
My understanding is that expressiveness (as per "On the expressive power of programming languages", Felleisen 1991 [0]) has to do with capabilities that a language has that separate it from another language. C is more expressive than Python in that it gives you direct access to memory management, whereas Python is more expressive than C in that it provides inheritance/OO. (These are just examples.)
Type safety, performance, and readability are all wholly separate from expressiveness, I think. A language's type system and performance benchmarks have nothing to do with the expressive power of a language outright, and "readability" is entirely subjective to begin with.
So: would you mind elaborating on what you mean, exactly, by "expressiveness of [a] language" here?
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In fact, most of what you (and the linked article) are talking about has to do with the dynamic/static spectrum, not this "wizarding/engineering" spectrum you've coined (though I do kind of like the idea of that for discussing development methodologies).
The article is all about how the dynamically-typed nature of Python allowed for rapid iteration at the beginning of the Instagram project, but has since hindered further progress as they've grown larger. But now they feel they can't just rewrite it all in a statically-typed language because of the engineering overhead involved.
On this note, I want to go to your last point:
> I wish there was a language that let you move gradually from one end to the other, exactly when you need to.
With regard to the dynamic/static distinction, there are languages that allow you to move "gradually from one end to the other", and they are (aptly) called gradually-typed languages.
Gradual typing was invented by Jeremy Siek and his PhD student, Walid Taha, back in the mid-2000s at Indiana [1]. In this discipline, you can have a statically-typed codebase with local dynamically-typed regions. You get all of the static guarantees for everywhere that they can be made, and dynamic regions impose runtime checks to ensure consistency. (This connects closely to contracts, which are primarily worked on by Robby Findler at Northwestern, I think.)
Unfortunately (to me), it seems like a lot of these languages are implemented in terms of existing dynamically-typed languages. For example, Sam Tobin-Hochstadt (Indiana) created Typed Racket, which is (of course) built upon Racket but provides a gradual typing discipline. Wherever possible, static types are checked, and everywhere else utilizes contracts to guarantee runtime consistency.
Anyway, all this is to say: the technology exists, technically, but is in its infancy. There's no doubt it'll be some time before it sees widespread use throughout industry. Sam wrote up a brief overview for the SIGPLAN Perspectives blog recently, if you're interested [2].
[0] https://www.sciencedirect.com/science/article/pii/0167642391...
[1] https://wphomes.soic.indiana.edu/jsiek/what-is-gradual-typin...
[2] https://blog.sigplan.org/2019/07/12/gradual-typing-theory-pr...