Singapore’s thriving globalized economy, founded on the ideology of meritocracy and conservative aversion to welfare provision, privileges industriousness, talent and competence, which works to justify the socioeconomic peripherality of a segment of the Malay community. These Malays are encouraged to acquire entrepreneurial skills through programmes run by privatized self-help organizations to attain social mobility. But privileging of Standard English as a necessary linguistic and cultural resource in such programmes results in linguistic insecurity, and the programme participants’ attempt to use English backfires due to their limited competence in the language. The analysis in this paper focuses on the anxieties involved in the positioning strategies that Malay participants employed in interviews and interactions during a micro-business training programme. Participants’ discursive strategies of adequation and distinction (Bucholtz and Hall, 2005) show how their linguistic insecurity about English reflects the tension between the prevailing negative branding of Malays as underachievers and their resistance towards it.