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2.) I'm going to take this REALLY SLOW. I'm only going to do one pass on the right side of my ugly-mug. What can I do to avoid getting nicked up?
Is there a similar, everyday type of thing that can give me an indicator of how much pressure to use? Something like slicing through mashed potatoes?
(Fear: I'm a manual labor kind of guy, and I won't have the right pressue, which will absolutely bludgeon myself the first time out.)
Don't use pressure at all. Lightly stroke your cheek with the blade. Keep the blade at a 30 degree angle away from the skin, or even flatter.
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3.) How difficult is straight razor shaving to get to a point where I can do it like driving? Meaning, I don't think as conciously about driving anymore, since I can just do it.
You shouldn't aim to shave that way with a straight. You need to pay attention to what you are doing. It's OK to be relaxed, but stay focused. Having said that, you develop motor skills within a few shaves, that may be more what you are thinking of.