Hey Ethan,
Good question you raise. I find the normal, middle-class lifestyle of North America does not offer much in the way of growth. So the only thing to do is go out there and put yourself in challenging situations that require you to grow and learn about yourself.
For me, I joined a youth leadership organisation at my university where I had the change to do a few exchanges in other countries that are vastly different from my native Canada and take on leadership positions where I was leading teams. These situations really helped to challenge me and when I look back and compare myself to what I was five years ago I can really notice the difference.
Probably any challenge you're interested in would do. Some possible examples are martial arts, sports, rock climbing, entrepreneurship, traveling, meditating, etc. etc. It doesn't matter specifically what the challenge is as long as you're fully interested in doing it.
I don't think it's so much a factor of "hitting rock bottom" as it is proving to yourself that you can overcome challenging situations and come out stronger as a result. That's what gives you the confidence and courage to tackle bigger things.
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