> When I see people in the startup world rolling their eyes at the "incompetence" of the enterprise world, I take it to mean they've never actually worked on a truly hard problem in their lives.

I worked in a related field in the past. I don't claim that the problems are easy - where I tend to roll eyes rather is:

- Bureaucracy: A lot is required by law, I know. But there is a difference between "just following the required bureaucracy in a minimal necessary way if it stands in the path" (the startup way) vs. "taking it seriously in a way that makes the work harder than strictly necessary".

- Hierarchies: Just three words: I hate them.

- Unwillingness (?) to tackle these hard problems: The problems are hard, as you already outlined. But this implies to me that everybody in the company will move heaven and earth so that the people who work on this hard problems are able to (e.g. give all necessary information (requirement specification etc.) they know of etc.). If there is just one thing (or even office politics) which will prevent that, I don't just roll my eyes, but get furious. Because of the hardness this is not to consider an obstacle, but targeted sabotage - and should be considered as such.