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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!
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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.