The management in the company didn't plan anything and the meandering development process showed it.
Please don't underplan. It's awful for morale to throw away work because of bad planning.
If your morale is harmed by throwing away work, that's something you should work on.
The promotion process explains way more of what I think you are getting at.
Then all the unknown unknowns become known unknowns and you can actually create good solutions to it.
All planning is a waste if you don't even know where the speed humps will lie.
[1] https://en.wikipedia.org/wiki/Chesterton%27s_fence#Chesterto...
If that's the place where someone is, they should be conferring with someone else who knows something instead of trying to fly solo
Blindly going through problem spaces is how you waste your life taking wrong approaches
If that doesn't kill your morale, I don't know what to say.
Meanwhile, by all means discover that no one likes typing numbers on a phone so you have to refocus on taking pictures of receipts and wage stubs and text recognizing them.
Although I should point out that 2/3 of the examples would not have been caught by a user, because they are compliance related.