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I think character develops proportional to however many states of brokenness and greatness you've achieved which practically means exposing yourself to lots of risk and novelty.
I tend to encourage people to take more risk (and pursue brokenness) for this reason because it's where the low hanging character fruits are.
(Though, when measured in outcomes and depending on which novelty you find me pursuing, I'm a bad poster for life philosophies. And it's not like I'm going to bloom into a saint someday regardless. I just like creating these oceans of awareness in me and I suspect others will too.)
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No, but most of us have to be willing to be broken to be great, and the will comes easier if you're already broken.
There are a surprising number of ways to be broken too. One way is to think money, beyond the Jones' level, changes more than life's trim. You can also force brokenness on yourself because brokenness is relative. Many people find what brokenness feels like in competitive sports.
I also suspect brokenness is more apparent in those with greatness because of the contrast.