It has nothing to do with courage. It's all about understanding our place in the world and deciding to take those fateful steps. The difference back when I first ventured out is that I was naive and as such, I simply did it and it happened that I didn't over-think it so much. These days, with all of the information available on the internet and tales from those of us who have come before, things should be much easier...and safer, yet there are still many who either over-think things or do not pay attention when it comes to advice about safety concerns.
Yes, one word...flats!