Most manager look to own projects that may return a modest multiple of their budget with a 80% chance of success.
There are few executives that will target an opportunity that is 100x their budget with a 20% chance of success.
To the company the third group of employees are much more valuable than the first and second because the returns on the winners vastly exceed the cost of the losers. Individuals however are cognitively biased against personal failure so it is hard to find individuals that will swing for the fences (and who can also convince people in group 1 and 2 to work for them).
Good companies create frameworks where it is okay to fail (i.e. doesn’t impact your job, advancement prospects, etc). Unfortunately that is difficult and it generally is easier to hire sociopaths (no joke).
unreasonable deadlines, non-existent documentation for existing systems, non-existent QA processes, unavailable/non-existent support staff, undocumented/unclear requirements, etc.
I would add: some organizations make fistfuls of cash and don't have much in the way of a technology team. Others pump billions of dollars through Excel macros. Not every company has a great IT team following all the latest buzzwords.