[slededit]

I didn't focus on OP because he already knows what he wants. Most people need help emphasizing with the other person not with their own wants/desires and compromise requires empathy. There are situations where someone is being over-accommodating and getting walked over but I didn't get that from the tone of the question.

Asking forgiveness later is another advanced level topic but it generally goes hand in hand with a good working relationship that has already been established. Without that its a quick way to get reprimanded or fired.

Remember, at the end of the day you are spending time on this specifically to get what you want. Its not an altruistic act for your manager.

[brazzledazzle]

Asking for forgiveness implies that there’s no formal rule or communicated informal rule. If you already asked you’re not asking for forgiveness. You can’t reprimand or fire someone for breaking a non-existent rule without looking like a total asshole which is going to destroy morale.

[slededit]

No that's not what "ask for forgiveness later" means in this context. It means you are breaking the rules and know you are doing so - however you think the net outcome is worth it. Doing this consistently and not getting fired is really an art.