Have been playing for three years or so and jam with once a week with a group of infinitely more experienced musicians. Also have been practicing with a 5 piece with a view to start gigging soon.
Although I have played a few gigs (mostly successful) and am improving slowly but steadily, I have never had the balls to play at a jam night.
Last night I took my drummer along to a local open mic for moral support, and lo and behold, managed to play for half an hour with no problems. Some material I knew, but some the house band guitarist showed me the chords. It helped that there were only a couple of other musicians in the pub so didn't feel intimidated.
That was a big deal for me, especially as I'm in my early 50s! Onwards and upwards...