The biggest roadblock keeping you from your goals is that nagging feeling in the back of your head saying, "I might fail."
Completing the Stranger Challenge subjects you to failure and rejection. You learn to stop letting that fear hold you back.
I nearly talked myself out of it a few times."They're busy". "I don't want to disturb them". Whatever. I pulled myself together and the very first person I asked said yes. It was actually kind of fun, but I feel doing something like this is easy when someone tells you exactly what to do. I don't think I would have done this on my own.