This paper defends a regularly paid basic income as being better equipped to tackle unfair inequalities of outcome. It is argued that the timing of "option-luck" failures – in particular, whether they occur early in a lifetime of calculated gambles, and whether they are clustered together – may lead to a form of "brute bad luck," referred to as "cumulative misfortune." A basic income that is paid on a regular basis provides a way to prevent the emergence of cumulative misfortune, because the basic income at least partially replenishes the individual's ability to take the next calculated gamble. The upshot of this is a nonpaternalistic justification for an unconditional basic income that is paid regularly and is nonmortgageable. This has an important bearing on the debate between those who advocate a one-off endowment at the start of adult life and those who advocate a basic income paid regularly throughout one's life. The paper contends that a regular basic income represents a superior social policy because it prevents the emergence of cumulative misfortune, rather than belatedly attempting to compensate for its effects during our senior years.