Right, iterating on your workflow is a normal part of work.
> I see a similar trend with org-mode users. It's great and all on a technical level (I've used it myself in the past) but it's easy to fall into the elisp and customization rabbit hole.
I think part of the issue is that people try to jump into the middle of something which has evolved without going through that evolution themselves. In other words, they need to go to the starting line and iterate from there rather than pushing through to the finish line. I have seen some complex workflows in Org mode, but those flows were built up over years.
The software analogy would be premature optimization. Developers attempting to use tools which are meant for scaling without knowing the how or why of these tools. If you don't know why you should use something, then you might not be to the point where you need it.
I learn the most about how to tackle a problem once I stumble across the need to fix the problem. The best tools are those I find when I then go in search for the fix.