"The idea behind stepping outside of your comfort zone is that you keep doing it until it becomes your new comfort zone."
No it isn't. The point of stepping outside your comfort zone is to see if it really does belong outside your comfort zone. Stepping outside your comfort zone and demanding that that be the new way, results be damned, is just as foolish as never stepping outside your comfort zone. Not everything outside your comfort zone is good and usually the only way to determine what is and isn't good is to jump in and try it out.
That's fair too. The point is that you do have to stick with it long enough that you can actually judge the results. If you've been outside your comfort zone for a long time and it's still not comfortable, maybe it's time to try stepping in a different direction. But if you just went to a meetup once and you felt terribly socially awkward and you never went back, how do you know whether it's because first meetings are always awkwards vs. you just don't click with those people?
No it isn't. The point of stepping outside your comfort zone is to see if it really does belong outside your comfort zone. Stepping outside your comfort zone and demanding that that be the new way, results be damned, is just as foolish as never stepping outside your comfort zone. Not everything outside your comfort zone is good and usually the only way to determine what is and isn't good is to jump in and try it out.