This paper analyses the workplace learning experiences of young male retail employees. Deeming formal education highly unattractive, the pursuit of lifelong learning and continuous development for such people relies on workplace learning. Their experiences, however, over several years and across various retailers painted a grim reality. Sector-level accreditation (at National Vocational Qualification level 2) was characterised as stigmatising and indicative of deficiency to prospective employers. These qualifications, indeed all formal in-house training, were positioned as lacking in quality, inauthentic and an unnecessary cost for employers and government. Effective learning was, instead, experiential and situated, with (limited) expertise cumulatively developed through doing the job. The paper moves beyond valuable, yet well rehearsed, arguments regarding which groups get access to training opportunities and a focus on upskilling those who are least qualified. Instead, this investigation asks whether current workplace learning provision in retail can provide genuine opportunities for advancement and development for "moderately qualified" young people employed in the lower levels of the labour market--a section of society whose learning experiences and needs are often overshadowed by a polarised focus between Not in education, employment or trainings, and those undertaking apprenticeships or HE.