Elaborating the relations amongst workers' learning, innovations and well-being is essential for achieving two important and dual goals in contemporary work life. The first is individuals' ongoing learning that underpins their employability and can respond to new challenges and emerging occupational and workplace requirements. The second comprises workers' remaking and transforming workplace practices, processes and outcomes (i.e., workplace innovations) in response to these challenges, and through them sustaining workplaces' productivity and viability. These dual processes of individuals' learning and remaking of practice co-occur and warrant understanding and supporting and promoting to exercise them optimally in achieving these dual goals. We aim to illuminate and elaborate these dual learning and innovations from the results of two studies of small to medium size Singaporean enterprises using interviews and observations. Framed by considerations from cultural psychology, work practice and well-being theorising, the dualities of workplace affordances (i.e., opportunities provided by workplaces) and individual engagement (i.e., how workers elect to engage and learn from these opportunities) are used to propose how workers' worklife learning and workplace innovations can arise reciprocally. In conclusion, sets of curriculum and pedagogic practices that can be exercised in work settings are advanced.