Maybe you should. Maybe you shouldn’t, I don’t know.
What I try to take into consideration is my pride, risk, motivation, what the outcome actually looks like if I get what I want, and what the total cost of ownership for me “winning” is.
I don’t believe there’s a formula for determining when it’s best to fight for something, but life experience helps, as does being proactive about decision-making as opposed to letting things just happen (as a result of time running out).