This article challenges positive views of the assumed relationships between skills, productivity and rewards in self-employed digital freelancing. It suggests that the upfront investments made by freelancers to build up positive platform ratings are not necessarily recouped in the form of increased autonomy, guaranteed work or more lucrative ‘gigs’. Drawing on 38 autobiographical narrative interviews and 12 audio working diaries with diverse online freelancers in Europe, we show how the low barriers to enter platform work provide opportunities for those with limited work experience and other commitments outside of work. However, the intense competition between an ever-expanding pool of (both skilled and unskilled) task freelancers within ‘digital tournaments’ results in the colonisation of worker’s free time, and the normalisation of unpaid labour. This implies that ‘free time’ for freelancers is largely an illusion. Furthermore, the significant ‘sunk costs’ that freelancers make in terms of time, platform-specific skills, reputation and networks are not fully recovered and cannot be transferred to other platforms.