I have been playing at jam sessions for over 3 years, and I feel like I'm starting to get used to it. One thing I learned is that if I want to play any solos I have to practice them until I can play them automatically, without thinking. Then, even if I suddenly get nervous or self-conscious, I won't make any bad mistakes. It's ok to make those little mistakes that don't screw up the timing, because no one notices anyway. But you can't make the big mistakes where everything goes haywire. If you practice the songs day after day, month after month, you can feel confident about playing them no matter who is listening.
Another thing I learned is that if I play the same songs every time, adding a new one only occasionally, everyone gets to know them eventually. Boredom is better than surprise with this. When they know your songs, it's more fun for everyone to play them together. We also get to know who can play breaks, or not, for our songs. I used to worry they would get tired of hearing me play the same songs, but now I realize it's ok.
If you want to introduce a new song, it should be simple and/or well known. For example, last night I played Blackberry Blossom, which I have been practicing but don't usually play at that jam session. It was ok because it's well known.
So, in general, if you want to start playing solos at jam sessions just keep it simple and don't be in a hurry to learn lots of new songs. Just get a small number very well practiced and play them every time.
If I play a song and no one seems to know it or be able to follow it, I usually don't try that song again. Or I might try it again months later, after I know it better. Sometimes they can't follow because I didn't play it right.
Last night I played about 4 songs without much trouble. In the past, I usually had problems with at least some of my songs. It definitely is getting better. I practice about 2 hours a day, more on weekends, and I record myself. I have been practicing seriously for about a year and a half. I used to practice only if I had the time, but now I make the time somehow.
In the past I screwed up a lot more than now. It didn't discourage me, though, because I knew I would get better if I continued practicing every day.
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Playing Since: 2003
Experience Level: Novice
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Played guitar, including folk and classical, for a long time, and started banjo in 2003, had 2 open-backs. Got my first bluegrass banjo summer 2008, and finally started learning Scruggs style. Got a Recording King Madison RK-R35 10/5/2011, my first banjo that has a bluegrass style brass tone ring.
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