"me ha tocado"
¿Cuándo me ha tocado superar mis miedos y ponerme en camino con muy poco?
When have I needed to leave my fear behind and set out empty-handed?
It's the "me ha tocado" part that doesn't make sense to me.
He's saying "overcome my fear" So It's like saying "When it has touched to overcome my fears"?
4 Answers
Tocar can also be used to mean that it's your turn. If you are playing a game, you might say to your friend, "Te toca a ti." It's your turn. So, I think it might make sense to translate it as "When was it my turn to get over my fears and start on my way with very little."
Another possible way to translate tocar is: (llegar el momento) hoy toca limpiar -> it's cleaning day today ahora toca divertirse -> now it's time to have some fun
According to this definition, you could translate it:
When was it time for me to overcome my fears and get on the road with the little I had? (Looser translation)
I'm not sure if that helps. ![]()
Tocar has many, many meanings, two important ones being:
1) to refer to the opportune moment to have arrived to do something
2) to refer to the responsibility or duty of someone to do something

Y si me toca la suerte..-- And if I should be so lucky, //if it was my turn to have some luck..
Somos unos privilegiados por lo que nos toca vivir. -- We are privileged in that we're living at this moment.
It's also used to give the sense of being obliged to do something. This is sort of the same idea of the translation of "llegar el momento" as Debiera said. In English we don't have a common phrase to directly translate this unless it is saying "to take a turn". To translate it as "when have I needed" makes good sense because that is the idea of being obliged to do it versus choosing to do something.