<p>Rational choice theories suggest people commit income-generating crime because it is seen as a quicker, easier, and/or more lucrative way of earning money. They also suggest incarceration can deter future instances of this behavior. However, individual-level variables could affect responses to sanctions. Prior illegal income may be one since it may act as a reference point for expectations of financial gains and success. The present study uses discrete-time analyses to investigate the effect of illegal income, incarceration, and incarceration length on self-reported criminal behavior across time. The sample consists of 7,347 person-periods derived from the Pathways to Desistance dataset. Higher illegal incomes are consistently linked to higher rates of income-generating crime. Meanwhile, the effect of incarceration is inconsistent, though the longest sentences are associated with lower rates of income-generating crime. There does not appear to be a substantial interaction between the two. Though present findings may be limited to specific sets of offenders; it seems prior success in criminal activity serves as a reference point for perceived benefits of future criminal behavior. Therefore, future researchers and CJ officials may to look into an individual’s illegal income as an additional factor when evaluating risk of recidivism.</p>