Just a follow up. Andrew's right in that the workstation must be on to delay send in Outlook. Now you have two options. You can set-up your computer to automatically turn on and off (http://lifehacker.com/5831504/how-can-i-start-and-shut-down-my-computer-automatically-every-morning), or your can delay send through gmail using an add-in called Gmail Delay Send (https://code.google.com/p/gmail-delay-send/). It's easy to set-up, just follow the instructions in the short video.