When Italy’s government started offering free reskilling courses for well-paid jobs in IT and construction, few workers signed up—a puzzle that led researchers to investigate. Surveying 1,100 unemployed Italian workers, they found that part of the problem was that career decisions are driven more by identity than income. Of those surveyed, only 38% said they would retrain, even when new roles paid better, because they feared a loss of status. Interventions providing concrete wage and job data modestly increased interest, but efforts to shift professional identity had some impact. The research suggests that to drive reskilling uptake, employers and policymakers must help workers envision themselves in new roles and clearly connect training to genuine career advancement.