How much time would I need to prepare before enlisting to make sure I have the best chances of passing selection?

It really depends on what your current fitness level is, however, generally speaking I tell guys who are modestly in shape to give themselves at least 8 months to get ready.

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What is your strongest motivation when you feel like you can’t give anymore? (especially in training)

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How do you keep your mind from second guessing and being wishy washy. When I’m training my mind sometimes wanders like "what if this what if that?"