If you're playing the guitar with a pick, the way the pick interacts with the string can make a big difference to how it feels to play the instrument, and to how easy it feels to pick notes.
One of the main things to be aware of here is the angle of the pick relative to the string.
Instinctively it seems like using the broad flat side of the pick should touch the string, but it turns out that this causes some issues. If you try this, you'll find that there's something like a ratchet effect happening, where it takes a fair amount of force to get the pick to actually move past the string it's resting on, plucking it as it goes. This makes for an awkward clunky feel to our picking. What we want is the pick to glide more easily over the string.
The solution is simply to hold the pick in such a way that the pick strikes the string at something like a 45-degree angle. This allows the pointed shape of the pick to come into play. The pick will now be able to guide itself over the string and impart energy into the string as it goes, making for a far smoother sound and playing experience. This is true for both strumming and single-string articulations.
There are two ways to achieve this angle, basically angling the pick forward or backwards. What I would call a forward angle is the more common, traditional grip, but either is better than hitting the string flat.
To angle the pick forward, hold the pick between the pad of your thumb and the side of your index finger. This will bring your hand into something similar to the OK gesture, except with the thumb going to the side of the finger rather than the tip. When we hold the pick in this way, we're able to adjust the angle of the pick by bending our thumb.
To achieve a backwards angle on the pick, hold it more with the pad of the index finger. The people who are able to successfully use this grip (and many great players have, Hendrix among them) tend to have thumb joints that can bend back, beyond a straight thumb. I believe it's called a Hitchhiker's Thumb. If you're not able to comfortably get your thumb back beyond straight, a backwards angle on your pick might not be doable.
Changing the way you hold the pick can be uncomfortable to begin with, as you'll be undoing some muscle memory. It will feel odd at first, but if you had previously been picking with the flat side of the pick, you'll feel right away how much more smooth and easy it is, so I would encourage you to make the change.
I speak from experience; I used to angle the pick backwards, but after something like 20 years of playing, decided to change to a forward angle. Although I hadn't been flat picking before, I still felt that a forward angle was a big benefit to my technique, once I'd got used to the change.
So, if you find picking tricky, analyse your grip and the angle at which the string contacts the string, and see if there's room for positive change. You might be surprised at the difference something so small can make.
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