Here's the deal. I have numerous e-mail accounts that all funnel in to my Mac Mail application. Some personal and some work. As most people who work online I find myself constantly e-mailing, but I have a small problem. I wear many different hats and find myself e-mailing first and asking questions later. This can result in me sending an email to someone from the wrong address, and in some cases it can be embarrassing and unprofessional to have a client complain that they didn't read an e-mail because they didn't recognize the address.
After scanning Mac Mail's preferences and trying to find a way to have it prompt me before I send each e-mail, I came up empty. There is a place where you can set the default 'Send new mail from:' but there is no setting for 'Ask me.'
If there is an easier way of doing this, please let me know, but without further ado, here is my fix to prevent me from sending email from the wrong account.
Begin by creating a new account and naming it 'Blank.' Use any e-mail and password and click 'Continue.'
Click through the 'Outgoing Mail Security' page and you will arrive at the 'Account Summary.' All that is left to do here is click 'Create' and this part is done. Once we are back at our main Mail preferences page, we need to change some settings.Highlight the new 'Blank' account you just created and then click the the 'Advanced' tab. Here we will need to un-check 'Include when automatically checking for new mail.' This will prevent Mac Mail from throwing an error every time it gets mail.
One last step in the preferences panel! By clicking the 'Composing' tab we will now select 'Blank' from our 'Send new mail from:' drop down. (If 'Blank' is not there, you will need to close your preferences panel, and then reopen. This forces the list to refresh.)
Close the preferences panel and create a new e-mail. Now your default new e-mail will always be sent from your 'Blank' account, forcing you to choose a valid account and save you from embarrassment.
In the event that you forget to choose, you will get an error box immediately. All you need to do is click the 'Edit Message' button to be returned to your e-mail where you can choose the correct 'From' address. 
The object here is to get me in the habit of always click the 'From' box before sending my e-mails. Seeing the error message is really annoying, so using this method will hopefully break me from my habit.There is one problem with using a bogus account, Mail will always think that there is an error with the 'Blank' account because it cannot login to it. The downside here is that a little exclamation symbol next to the 'Blank' account and 'Inbox' label. It's a harmless annoyance, but it's worth it for now.
Hope this helps! If there is a better, easier or I just missed a setting that makes ALL of this go away, let me know.
Leave a comment if this helps you.
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