Is this a hill worth dying on?While I have been hard pressed to find a definite origin of the phrase everyone seems to believe that it embodies the question of whether or not "something" is worth committing all of your resource towards. In military terms it denotes a spot (a hill) that you believe you need to continue your offensive. In humanistic terms it means something that you believe in so strongly you are willing to fight to keep or gain.
It is an interesting question in that if you sit back and really think about it you eventually end up going through your list of priorities and determining whether or not this particular item deserves to be in the top rank with your other priorities. You need to evaluate the effort to attain that goal or objective versus the effort to go around and try alternative approaches. You need to objectively differentiate between "wants" and "needs". You need to be able to think about long term goals and whether or not your effort should be expended now or saved for later.
Sometimes it doesn't matter.
Every so often you come across something which deserves to have a line drawn in the sand. Something happens and suddenly this is a hill worth dying on. Whether it is the 17th similar event that has occurred or whether it is the 5th different event but on the same day, every so often the switch flips and you rise up, ramrod straight, hold your head high and say "no".
A leader will find a hill worth dying on because it is the right thing to do. A manager will find a hill worth dying on because you are violating policy 62A, Section 2, paragraph 3a) and 3b).
No matter what, however, it is your choice.