Earlier quoted context omitted.
At my last job, my boss was very guilty of "At ____, we found x to always cause us problems", but he never really connected that "x" was a problem because of the context surrounding it, not inherently. We went through this really awful process of: Manager either demands or rejects an idea based on a totally different company -> I spend days/weeks proof of concepting/documenting/testing/validating for or against his m…
Yeah it absolutely can be an endless process. Human imagination is endless. You can't 'try catch' for everything that has happened sometime, even more so when addressing it at a high level without detail / nuance. You easily can get nothing done.
That's exactly what we did. A year spent conducting experiments to validate or invalidate positions based in dogma rather than building, iterating and adding value.