Whenever it is possible, a boy should choose some occupation which he should do even if he did not need the money.

Phelps is advocating a vocational ideal grounded in intrinsic motivation rather than financial necessity. The “even if he did not need the money” clause frames work as a form of self-expression and character formation: the best occupation is one a person would pursue for its own satisfactions—interest, service, mastery, or joy—because that kind of commitment tends to produce excellence and resilience. The gendered “boy” reflects the period’s common assumptions about career choice and public work, but the underlying counsel generalizes: when circumstances allow, choose a calling that aligns with temperament and values, so that livelihood and meaning reinforce each other rather than compete.