I-deals are a key method for organizations to retain and motivate employees, yet little research has investigated employee motivations for seeking i-deals and antecedents to request and receipt. We examine these largely invisible antecedents of i-deals in the context of older workers, a cohort of increasing importance in the workplace. Through thematic analysis of 82 in-depth interviews with Australian workers over the age of 50, we develop a model of i-deal emergence that delineates the motivation, request, and receipt stages of i-deals. We identified four motivational influences to seek i-deals: to improve work–life balance, to repair psychological contract breach, and to craft satisfactory retirement pathways; high levels of existing job-role autonomy acted as a demotivator to request i-deals. We also identified three factors associated with an i-deal request being granted: an older worker’s value to the organization, positive employee–manager relationships, and emphasis of mutual benefit for employee and employer. We identified a novel antecedent for i-deals: feasibility—an older worker’s perception of how likely they are to be successful when requesting a desired i-deal. Feasibility perceptions are informed by organizational practices and policies around i-deals, co-worker i-deal experiences, and job-role constraints. Feasibility can influence an employee’s decisions to request an i-deal and also directly affect attitudes toward the employer, regardless of whether an i-deal is present, desired, or otherwise. Theoretical and practical implications are discussed and future directions outlined.