Translating the analogy back, what you describe is the entrepreneurial fail-until-you-win method. The alternative method of progression is that of apprenticeship or gradual promotion, which in my country is associated with traditionally middle-class professions like finance, medicine and law. In such a conventional career, success is almost guaranteed, as the number of people entering the profession is very close to the number retiring out of it, and the assumption is that, because the endeavour has always been profitable, it will be for you too.
Ideally, the profession as a whole gradually improves under this system, but no individual member of it has to engage in any more than an average level of risk to be personally successful.