"The thing I do best in the world in a professional sense is writing, so if I were to become rich, getting rich through writing seemed like the most likely way for me to do it."
And this is why kids should learn about bayesian probability https://en.wikipedia.org/wiki/Bayesian_probability in school. Otherwise, they will continue to make decisions based on such faulty logic
Being a good writer isn’t some useless skill in a basic office job. I think you are reading some implication into his statement that isn’t there, like he’ll only try to become a famous writer, indefinitely, into homelessness if he fails.
Maybe the plan was to take the unlikely but high payout chance (successful writer) and then the failure-path is basic office job or something.
