While the Nordic countries represent a zone of penal moderation, drug offences remain subject to harsh punishment. Based on 60 interviews with incarcerated drug dealers, we present four trajectories and turning points to the higher tiers of the illegal drug economy. The first trajectory is characterized by criminal entrepreneurship, but three other trajectories were equally evident: (1) Many drug dealers experienced poor parenting, parental substance abuse and early involvement with substance-using peers; (2) for others, marginalization processes started in adulthood, related to job loss and the breakdown of intimate relationships; (3) for some, drug dealing was interwoven with substance abuse. The findings suggest that drug control policies rest on misleading ideas about the trajectories of persons convicted of drug crimes.