Short Description: By the time you reach the end of this article you will be able to hold a pick comfortably and strum your way to joy. You may lose picks sooner than you had ever thought of. So see to it that you always have a pick when you need one. They come pretty cheap. You can get a standard pick at less than a dollar.
So, don't be tightfisted while spending on picks. Buy the ones which have medium thickness and are neither too soft nor too hard. Now that you have a reasonable number of picks with you, let's start learning how to hold them properly.
Relax your picking arm and let the palm face you. Gradually fold your fingers into a lose fist and rotate your wrist till the knuckle of your thumb is in line with your face. Slowly slide the pick between your thumb and index finger. Keep sliding it inwards till only about a third of the pointed end can be seen. If you let the pick hang out more either it'll fall off or you'll end up in ungainly tangles while picking the strings. Once the pick is nicely nestled between your thumb and index finger roll open the other fingers.
Hold the pick firmly but don't clasp it hard else strumming becomes muted. It might slip off a few times in the beginning but soon you'll be used to it. Just push it back if it slips.
Sling your picking arm gently over the body of the guitar and rest the pick on the third string just above the sound hole. Plant your other three fingers on the face of the instrument. Then, without moving your wrist, let your arm fall freely using elbow as a pivot. Stop the moment you've picked the lowest string. Repeat this exercise starting from the topmost string till you can strike all the strings as your hand falls across them. See to it that you aren't missing any while moving down.
Now try to pick your way upwards, without moving the wrist of course. Just brush the strings as you move up. You might not be able to hit all the strings - you needn't anyway. The up strum is usually "off beat" and always weaker than the down stroke.
Repeat these movements till you're comfortable holding the pick. But let me tell you something. Legendary guitarists like Eddie Van Halen, Jimi Hendrix, Mark Knopfler had their own unique way of holding the pick. So, don't be too picky about "how to" hold a pick.
Hold it the way you feel most comfortable and able to freely strum the strings. That's all.
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