We're guitar players. Let's be honest. We crave praise. We love being the best player in the room. It's a great feeling when all of the preparation you've done in your life brings you to that point of mastery...When you have the confidence to play without fear...it's a trap...
The need to achieve, to be the best player in the room can get in the way of real progress. We start avoiding situations that take us out of our comfort zone. We avoid the embarrassment of possibly making mistakes. Once this mindset gets a hold on us, it can turn into a narrowing of your playing experience. Slowly you start taking gigs that are only safe, and soon that feeling of being the best in the room isn't enough to satisfy you, and then the whole experience starts to suffer.
In my early 20's I started to actively seek out musical situations that pushed me out of my comfort zone. I showed up at a recording session with seasoned jazz players who had all been working together. I was the unknown player, and straight ahead jazz has never been my strong suit. I tried my best to not let that affect my ability to contribute musically to the situation, and I focused on enjoying the music, and the considerable skill level of the rest of the band. On break, I asked a lot of questions about phrasing. I took the risk of being the annoying guy bugging everyone, because they had a skill that I wanted...I ended up making some friends that day, and my brain grew bigger, as did my vocabulary...by the end of my session, I was a shade more comfortable hanging with those guys, and that comfort level grew a bit more each time we got together...until the next left turn in my playing experience threw me into another arena.
If ever I want to shake up my playing I listen to music that intimidates me, and I break down what I can, starting with the lines that strike me as the most interesting. I always try to remember that, no matter how bad I may sound on that day, I still have all of the skills that I have worked on my whole life. One day of sounding bad does not negate all of that work, and it might be exactly the thing that pushes me to the next level.
So, find that guy whose playing intimidates you and talk to him. Jam with him. Let him embarrass you with his ability. If he's any kind of musician, he's listening intently to what you are doing to try to generate some new ideas of his own. We never know what is going to spark the next level of development.
As always, music is a language. If someone uses a word you don't use, or references a book you've never read, try to avoid that instinct to pretend you know what they are talking about. Ask questions. Be vulnerable and honest. Not knowing something doesn't make you less of a person, or less of a musician. Our experience is vast and very personal to us. See every conversation or musical experience as an opportunity to learn something new. Proudly be the worst player in the room.