Good insights, Marly...
As a surfer, I've always believed in what I call "pushing the envelope." I should probably write a post about that one day, but briefly, this is what I mean...
When it comes to surfing, the only way to learn is to attempt things you've never tried before. However, this needs to be done cautiously. You never want to get off of a two foot wave and suddenly decide to try a twenty footer!
In other words, pick a challenge that is just a little beyond your "comfort zone," and then learn from it. You may get beat up a little, but you're less likely to die. And yes, of course, know when to quit and come in, happy to live to surf another day!
Hugs, dear!