How to approach your boss for something?

My leave application has been bugging me for the last few days. A week ago, I approach my superior to approve my leave. It is only a 2 days leave, to my surprise he rejected me. We were towards the end of the project and our deadline is tight hence he froze our leave application.

He didn't rejected my application outright but requested me to submit to the HR dept as the manager was compiling a list of who are taking leave. What can I do? I obliged.

Then I did the unthinkable. I purchased the ticket without waiting for the confirmation. Regretted the move? Well yes in the beginning & no for the ending. I waited for a few days, unfortunately no news. The event really making me nervous. I have spend a good 2k on the flight. What if my leave not approve? This question keeps running through my mind.

Unable to sleep well for a few days, I was thinking a way out of this. I have a few options on hand.

I bump into him today and take the opportunity to try my luck again. I dragged him to a room and close the door. I was looking down on the floor with my back facing him thinking of how to start. I turned around and admitted my mistake (for not having my leave application approve prior to ticket purchase). I looked at him and told him I booked the wrong date. Therefore I requested for my leave to be approved. To my surprise, he verbally agree to it within seconds. I was thinking what the heck, if he has agreed to this earlier, I wouldn't have sleepless nights.

Lessons learned:

1. Talk to your boss when his mood is good.

2. Be honest and admit to your own mistake. The worst you may get is a bit of scolding. At least your integrity is still intact.

3. Make eye contact. Look for signs.

Am I happy for what I am doing?

I have view Steve Jobs' speech at Stanford University a couple of times. It never fails to impress me everytime I watch it. One of the part that really hit me hard is when he said "Your work is going to fill a large part of your life, and the only way to be truly satisfied is to do what you believe is great work."

From that point on, I kept asking myself am I happy for what I am doing now? Do I love my job? Sad to say my heart says no.

I recall what my former superior, HS, advised me before I left. I don't remember exactly what he said. But it means something like don't work because of money, you wouldn't be truly satisfied. At that time I didn't think too much about that. With the salary I have at that time, I told my ex that I wouldn't know when I can buy a house and settle down comfortably. That was 3 years ago. Today I am really sure I need to change something to get my life back. I need to be in control of my life and do what I love. I am striving to achieve that.

Where should I go from here?

I am been thinking on my way home today. What should I achieve? Or shall I say what should I do in order to move up?

There's a few thing that I have in my mind:

1. Make sure your boss(es) know what are you doing. Promote your work especially those that are dear to them.

2. Know your boss(es).

3. Work on high profile projects and make sure they are successful.

4. Help in saving cost for the company esp those big recurring bills.

5. Networking esp with those that are in the same field as yourself.

6. Keep yourself updated with technology.