The biggest courage-building phase of my life happened in my late teens, roughly from age 17 to 19. But it wasn't job- or business-related... unless you consider shoplifting a job. After getting out of jail and going through a few years of working on my personal growth, I was a very different person courage-wise. Risking all my stuff to pursue an interesting business idea didn't seem like a big deal compared to risking jail time on a daily basis. So that experience gave me a different perspective on courage than most.
Courage is a mindset though and has very little to do with external results. You may think that enjoying an easily maintainable positive cashflow would make it easier to be courageous, but I usually see the opposite in people who have high incomes or lots of material possessions. They get so attached to their stuff that they become even more fearful -- of losing it. For some people their stuff becomes part of their identity and self-worth, so anything that threatens the stuff threatens the self. People can become very uptight and controlling when they start earning a lot of money, and it actually drives them further into scarcity thinking rather than being an expression of abundance.
Courage-wise I think it's easier to start doing what you love when you're totally broke and even in debt because you probably don't have much to lose anyway. Many people fall into the trap of thinking they should get rich first doing crap work, and then they'll have the freedom to do what they love. Erin and I have seen the long-term results of people who've pursued that path, and most commonly the person will just keep distracting themselves with one excuse after another. Year after year it only gets harder -- never easier -- regardless of how much money is amassed.
A lack of money or income isn't the real obstacle, but it's a very popular excuse.
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