As a convert from a non-JW family, I know it was easier for me than for many born-ins whose whole family are JW's.
At about the age of 27, I realized I was very unhappy. I started going back in time to figure out what had led me to the situation I had gotten myself into. It went back to my trying always to escape my family. Being away from my family was one of the rewards of becoming a JW when I was 15. At the beginning, being a JW actually opened my world and gave me broader experience, but, as time went on, I realized it was holding me back.
I don't know if one group (born-ins vs. converts is more likely to get out, but I am certain that it's easier for converts.