Asking Permission vs. Telling

I think I am getting better at following the rules that Sir has set for me, and asking permission for extensions and the like. Especially concerning bedtime. I've been in bed by 11 pm, or I've asked for permission to be up later. This week, I needed to get something for work, so I asked for permission. A few times in the past, I've been up doing work, prepping for an interview, or spending time with family. I can think of one instance where Sir insisted that I keep to my bedtime, and I had nothing crucial to do.

If I have a good reason, Sir will give me permission to stay up later. I am thankful for this. He is being understanding, and making sure I can get things accomplished, within reason. I feel that I am reinforcing my desired role by stopping to ask for permission over just doing things. A month or so ago, I stayed up about 20 minutes extra without asking permission, to do prep for an interview. I figured I was following the spirit of the rule. I had been allowed to prep for interviews in the past, so why not now? I didn't get into trouble, but I now think I should have asked permission anyway.

Lately, for the past few instances of asking permission to be up later, I almost feel like I'm telling my Sir instead. I don't expect to be told "no", so even though I'm asking for permission, I feel as though I am informing him. I asked him the other day if I could stay up late to pick up supplies for work. But I didn't really think he would deny me. I had already planned the rest of my evening around it. I think now... what would I do if he didn't allow me to do so?

At my environmental job, we often assess situations by asking "what could be done to prevent this, or handle it better"? I've started applying that to my daily life. What would I do if Sir didn't grant permission? For certain situations, I could have gotten up earlier the next day to compensate. I could also ask permission earlier in the day instead of a few hours before bedtime. That way, I have more time to consider alternatives if his answer is negative, and it gives him more freedom to actually consider denying me if it his wish without feeling like he's putting me in a bad situation.

Or I could learn to manage my time better overall.