It may hurt more than the first time because there will be scar-tissue where the original hole was, meaning more pressue will have to be applied. But if you were ok the first time, I'm sure you can take it again!

There are 365 days in a year

Of course! As long as the person stays on their medication and keeps a steady relationship with their therapist. It would be a good idea to notify your employer of your situation, but let them know that you have the symptoms under control the best you can.