I love this! And I love that you're choosing to talk about failures, because you're right, we keep hearing the success stories and so we expect success. But more people fail than we think. And that's ok. In a way, failure is a form of success. It means you followed through.

I like your idea of cautious ambition. In a way I'm kind of living it now. I quit a full-time well-paying job to focus on my writing, but I do keep a part-time job to pay my bills. It only barely covers my expenses, which gives me motivation to hustle on the freelance side of things.