Obtaining and maintaining employment is one of three dominant factors (along with marriage and military service) in explaining desistance – why and how people stop committing crimes. The search for effective recidivism reduction strategies has increased, despite their lack of success. In many cases, recidivism was not reduced, and in some instances it increased. Recognizing the criminal mindset or “criminal thinking” is important, for it must be addressed and changed if the offender is to have a decent shot at obtaining and keeping a good job. Job retention is often a bigger challenge than the securing of a job. This mindset is generally not supportive of legitimate employment and the behaviors required to sustain it over the long term. The risk that we run when taking the approach of jobs first is that we will send offenders to work without the preparation and skills they need to cope with the contemporary workplace. In addition to vocational counseling and job preparation services, we need to expend the resources and take the time to ensure that the offender we send out to work is as ready as possible and has the right mindset to succeed in the workplace.