Send the letter or not?

Say you have a job in an office. It’s a good job and you’re happy with it, all things considered. However, you think it would be rather nice if you could have a raise.

You write an email to your boss stating why you think you’re worth a raise and other details to support your point. The email is ready to go.

At this point there are three possible outcomes:

1) Your boss reads the letter and agrees that you are, indeed, worth the extra money. You get a raise and your life is (presumably) better for it.

2) Your boss reads the letter and thinks you are worth the raise, but the company is a little strapped for cash at the moment so you won’t get one. This is OK with you because you are pretty happy where you are, anyway. The status quo is maintained.

3) Your boss reads the email and decides that because you are requesting a raise you are no longer happy with your situation. The company is strapped for cash and he decides to be pre-emptive and let you go.

Would you send the email knowing the three possible outcomes?

As a bonus question: Would you send the email if you already knew that the company wasn’t in a position to start handing out raises?