A great reason to set up a rule in Outlook to delay delivery by 1 or 2 minutes, like I have. I have too many similar names in my address book to let my instincts take over (click click click, ctrl+enter, d'oh).
1 Tools > Rules Wizard...
2 click New...
3 choose "Start with blank Rule", select "Apply this rule after sending"
4 click Next... do not choose a rule at this step
5 click Next... click "yes" to prompt
6 choose "defer delivery by a number of minutes" rule, click "a number of", enter delay time