Nitpicking, but you were expected to succeed by default, and also taught to strive for success by default (and presumably also taught the tools and approach to maximize likelihood of success). People cannot be taught to "succeed by default", anymore than someone could be taught to "win the world series by default".
And then that unpacks the challenge of this particular world view (and points at why the 'self-esteem thing' is a thing), is that learning to strive for success, and learning the tools and methods to achieve success does not mean you will actually reach success (this would just be a variant of the just-world fallacy). The challenge is how do you create the motivating factors and structure for as many people as possible (hopefully everyone) in your society/culture to earnestly strive for success, but not crack apart when they encounter continued failures.