Have you ever regret for sending mail to a wrong person or wrong information? Almost everyone does at some point of time. Some people does frequently. 
And then they regret it and furiously try to recover the mail.
Here is the tip: Use Outlook Rules and Alerts feature to delay the mail sending, say a minute. So every time you send a email, it will sit in Outlook for a minute before sending. It gives time decide if the mail really wants to go out.
How to create the "Defer Delivery" Outlook Rule?
1. Click Tools –> Rules and Alerts… in Outlook
2. Select "Check messages after sending" and click Next
3. Do not select anything in "Step 1: Select Condition(s)", just click Next.
4. Check the box for "defer delivery by a number of minutes". In Step 2 section, click "a number of" link and select 1 for one minute. Click Finish.
5. Close the Rules and Alerts window. You are done.
Now every time you send a mail, it will sit in Outbox as I told before. Hope you are happy with the solution. 
Anand, the Architect 