Thank you! Do come in, the water is fine. If you keep Python for it's applicability today and pick up Common Lisp for it's practicality tomorrow, I don't see how you could go wrong.
Emacs is the weakest link in the Common Lisp experience but, yes, you have to defeat that boss to move up. I love/hate Emacs and mostly struggle to do anything. GNU Emacs is a ball of mud with decades of technical debt in dire need of a ground-up re-imagining. Emacs Lisp made a lot of inexplicable choices but it is a Lisp and Lisp is why Emacs survives. RMS' stewardship has been consistent but underwhelming. He's no Jose Valim. The editing model is inadequate, as shown by Kakoune and structural editors. And yet, Emacs is alive and malleable while so many other editors/IDEs are inorganic artifacts that start to rust as soon as they are released. We do have the nascent Alive for VSCode and VIM options, but they are not really improvements over Emacs, nor are they likely to be. VSCode is the latest CodeWarrior and will suffer the same fate. It's only propped up by daddy's money.
Doom Emacs tooling, package management, and sensible defaults take much of the pain out of Emacs. Sly, the LSP-like Emacs mode for CL, is too much fun and gives a hint of what Lisp Machine development must have been like. Remote editing and daemon mode are so practical. Once you've painstakingly hammered out a config and workflow, Emacs starts to hum along pleasantly. But getting there is relentlessly frustrating and trying something new sends you right back to the treadmill. Once I figure out why Lem SDL2 (an Emacs clone in Common Lisp) isn't building for me, I'll attempt a switch.
I have daily fantasies of jumping back to my high school graduation in 1986 with everything I know now. I'd put up sexy posters of Guy Steele and Alan Kay in my dorm room. The only real advantage of starting programming at my age is that I know what I want and why. I'm following the humanistic thread of computing from Paul Otlet -> Vannevar Bush -> Doug Englebart -> Ted Nelson -> Bret Victor. But I read the same chapters over and over and still haven't written any code beyond homework exercises. The task feels Sisyphean and my trauma-addled, post-alcoholic brain struggles to stay focused. My only consolation is that I can't think of anything better to do with my remaining time and the Common Lisp community is good company. I love being around eccentric people who are much smarter than me.
Python is an eminently practical, perfectly respectable choice. So naturally, my life goal is to kill it. In my head, Symbolics was open sourced after the AI winter and grew to become the obvious choice for most tasks. I wish that people wrote new languages as DSLs on top of Common Lisp rather than littering GitHub with vanity projects that die on the vine. Think of all that wasted effort--like turning up the thermostat with the front door open.
When people ask about the choice of Common Lisp or Scheme, I ask which Scheme? No two are alike and none of them has achieved enough momentum to be truly practical. You have to pick one and pray your requirements don't exceed it. In CL, we invest in implementations--ABCL, ECL, Clasp--each one practical, each one mostly runs your code unchanged. Our spec is ancient by today's standards so old code just works. We innovate in our package ecosystem which gives users of whichever implementation access to fresh work. Compare to the whitewater churn of the NodeJS ecosystem. I have a Ghost blog that's a few years old and I can't update it as things have changed so much there is no practical way.
I'd like to file off the most common pain points in CL, spackle over obvious gaps in functionality, improve documentation, and polish the developer experience until nothing stands between Lisp and world domination. It's the once and future language. I have no qualifications for the job whatsoever except resentment of the status quo, a burning need for elegance, and lack of employment. It's a short resume, but the nice thing about being self-appointed is that no one has to want to hire you.