I believe enduring something that threatens your life or what you care about is easier to do than charging into dangerous territory. This is why the first contest–the easiest–associated with learning toughness would withstanding. Will you withstand or will you cave in, give in?
Now we come to the second contest: charging. And the question is: how do you teach someone to charge, almost to the point of rashness or hot-heated boldness? What is puzzling about this particular “how you teach” question is that I’m a philosopher and philosophy, regardless of its background or commitments, takes place as one is stepping back and considering. A philosopher wanders, wonders, and considers, turning (as it were) the whole world over.