Part of the difficulty though is you have to "put yourself out there" and get a little out of your comfort zone in order to gain experience
On the other hand. Why drive around in third gear when your car has six?
You're both correct, you do have to push your limits to gain a certain level of experience. But there is a difference between pushing your limits and blowing right past them.
I can't count the number of times in my early days I went warp 9 through my personal limits only to get that sick feeling in my stomach and praying to get back on the ground. I wish I had of had the resolve to take it in manageable steps, but alas I'm a masochist.
Who knows, maybe the guy had a very bad crosswind experience or their first flight instructor said something that stuck. An early school teacher of mine once compared mushrooms to toe jam - they're both a fungus. 30 years on there are 20 kids from that class, myself included, who still cannot eat mushrooms...maybe something similar happened to him.