Don Greene's book Fight Your Fear and Win encourages people to create a 21-day courage log as part of their way to convince themselves that they are risk takers. One of many things that I did as part of that 21-day exercise was to go to local jam sessions. There is one in Raleigh, NC that is mostly rock and roll, but really any genre. Playing in a free-form jam session has been so good for me because I get to experiment in so many ways. It works on my improv, how well I work with others, and is the best "real time" aural skills test. Most of all, it's risky!
Thankfully improv has always been encouraged by my teachers. Tim Hudson and I would frequently do classical improv using pentatonic scales. Wiff Rudd does it frequently with his studio at Baylor University. I have had the pleasure of participating a few times, and always had a wonderful time. Professor Rudd argues that improvising as a studio is where students often find their unique sound. These experiences combined with the experiences I've had in jazz band in high school and undergrad greatly enhanced my trumpet playing and musicianship. I'm finding that taking risks is a much more enjoyable way to live as well.
Time to take more risks, and keep exploring
Adam C White