Early in my career I had this. I was given a task and a deadline, and told to prepare a plan. I estimated the plan, and it came out to longer than the deadline. I presented this, only to be told "but that's longer than the deadline! go fix it!". So I shortened all the estimates and it fit the deadline. When I presented this I was shouted at for shortening all the estimates, and told to go back and do it properly.
Around this point the penny finally dropped that software estimation is a political process, not a technical process.
Around this point the penny finally dropped that software estimation is a political process, not a technical process.