I have a pretty good idea that lisp would fit into how I like to develop software.
The biggest thing that I'm looking towards lisp for is interactive programming. Python is currently my primary language, and I heavily test/prototype things in the REPL as I'm programming or dropping into one for debugging.
Additionally, I like the things you get with a complied language but have zero interest in going deep (I know them and have used them, but not professionally) with the standard C derivatives of C, C++, obj-C, and Java. I'm also pretty tired of many of the gotchas in python with its bolted-on-type system and is essentially a wrapper around C. I love the libraries and functionality, but the amount of boilerplate and testing needed to produce reliable code has burnt me out on it.
I'd probably go with Swift and SwiftUI if it weren't Apple only and still limited in what it can be practically used for, such as building deployable web services with it.
The other thing that has always lingered in my mind is the promise of DSLs/functional programming/etc. or other abstractions that never lived up to their potential ergonomically in other languages. I'd start using them but almost immediately run into edge cases that required workarounds to get working. After a while, I would abandon them entirely because the workaround added up to not being cleaner overall or leading to lower readability and maintainability.
Like function composition, I'd love to have functions that are generic work loops/data pipelines that I pass in different data and business logic/conditionals to. Still, in python, it's challenging to do that cleanly/maintainable. Or even some of the basic stuff Ruby does with metaprogramming that ends up being a nightmare to attempt in python. Even javascript does better with functional programming than python or any C derivatives.
So I have a fair sense of why I'm leaning towards lisp. I'm more interested in jumping in and using it for practical things. For example, I want to write a web API that uses SQLite. How do I prototype and test that using lisp? Kind of a “working programmer’s guide to getting going with common lisp.”
Oh, I'm also currently an independent software developer, so I don't need to worry about external constraints.
I will read On Lisp first, though! I just read the preface, and it directly addresses several of my desired outcomes.