My freind (who is also out) and I were talking about this the other night. I was a born-in, 3rd generation JW and she converted when she was in her late 20's.
When she left, she said that she knew the world wasn't as bad as she was told as a JW, so she knew she would be fine. Also, she still had lots of "worldly" family who welcomed her back with open arms.
It was harder for me - I had nobody in the "world", no family or freinds. The "world" was portrayed as an unloving, evil place full of bad people, so it was scary to leave the safety of the JW's.
We both agreed it is a bit harder for Born-Ins to leave. Although it is hard, no matter who you are.
What do you think?