Normally a subscriber will only be in one sequence added from any one automation a time. The reason being that they are effectively paused in the automation until they complete the sequence, and then they continue.
With your automation, the event will pull the subscriber down to that point. So at 12:25 on the 21st, any subscriber in the automation will be pulled down to that event branch, and added to Test Wake Up sequence. They will stay there until that sequence finishes, and then leave the automation.
So I don't think it will be possible to do this in the same automation. Anyone else got any ideas on this?