Just do it till it doesn't bother you anymore? If you know it's deep enough, and you know you won't get hurt, then isn't it just like hopping into cold water? Do it, get it over with, do it over and over till it doesn't bother you anymore.
Assuming you don't have a crippling phobia, of course. I'm not trying to say if you're frickin terrified to just get over it, but you say you're "hesitant" about it. Seems to me if you do it enough there will be no more hesitation.
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