I've been humbled many times, but often in the context where I do not have anything to lose.

When I was a musician, I'd met people that were infinitely more talented and hard-working than me. When I was in college, I'd met people that were just better than me in everything.

But I'd say that my first "real" humbling came when something critical I made at work stopped working. Suddenly I'm the one responsible for a xxx million dollar system not being operational, and all the people that are dependent on it.

Every time I see some major apps / sites being down, I get flashbacks, and feel the immense stress some people are going through.