Sometimes it is the small things that make a big difference in your guitar playing. I generally don’t do a lot of product endorsements, but every now and then I find something that I think is worth sharing. This is one of those times.

DO try the National brand thumbpick. It costs slightly more, but the precise shaping and contours are worth the extra 30 cents!
Recently, I have been getting into a lot of country blues finger picking on my steel string guitar. I have been working out some fingerstyle arrangements by Chet Atkins and Tommy Emmanuel and, in accordance with their styles, this means using a thumbpick. I have tried several times in the past to play with thumb and finger picks, but I’ve never felt comfortable playing with anything other than my own fingernails. As is the case with most things in guitar, persistence is starting to pay off. I am getting the hang of the style and I’ve realized that your choice of thumbpick can make a big difference in both comfort level and ability to control the sound of the bass strings.
It turns out one reason for my prior frustrations was that I was apparently using a a poorly designed thumbpick which was also the wrong size! Not to name names or anything, but I was using a medium size thumbpick made by Dunlop. At first the medium size pick felt snug and secure, but after about 10 minutes, my thumb started to feel squeezed an was turning purple (yikes). Also, the pick seemed very long and kept getting stuck in between the strings, making it hard to play the bass strings with any subtlety.
Alternative Solution : Try a Different Thumbpick
I went back to my local guitar shop to see if they had any other picks to chose from. The Dunlop was all they carried. Then I started looking around online and I found these thumbpicks made by National. I found many reviews stating that these picks were designed better, with smoother contours, and that the actual pick end was shorter. Seemed like everything I was looking for. So I ordered a pack of them and hoped for the best.

Tommy Emmanuel (left) & Chet Atkins (right). Two of the all-time greatest fingerstyle guitarists. Circa 1997.
When they arrived I felt like Cinderella ;) They just fit perfectly and played so easily. There are times when guitar playing is physically uncomfortable and there is nothing you can do about it. Sometimes you just have to bear down and work through it. But in this case I was really glad that I spent a little time looking for alternative solutions, because the awkwardness of the Dunlop pick’s shape and the physical discomfort of it being the wrong size were totally unnecessary.
Of course this begs the question, how do you know when to work through discomfort and when to look at changing up your gear? The best answer I can give you is to ask your guitar teacher. We learn these kinds of things the hard way so that you don’t have to!
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