He probably paced this out by foot, or maybe using an odometer, with wheels that turned gears that measured distance by dropping a ball into a bucket at set intervals.
Finally, to prevent the Enigma from being a simple substitution cipher every single time a letter was entered, the rotors advanced by one spot, sort of like an odometer in a car.
When I say " total amount of winding" , I want you to imagine an old-fashioned odometer that ticks forward as the arrow spins clockwise, but ticks backward as the arrow spins counterclockwise.