The Industry 4.0 (I4.0) advent is re-shaping the way systems and processes operate by considering Cyber-Physical Systems combined with a plethora of emergent Information and Communication Technologies (ICT), e.g., Internet of Things (IoT), Artificial Intelligence, Cloud Computing and Intelligent Robotics. However, the emergence of such disruptive technologies strongly establishes a demand for upskilling and requalification of active professionals and young undergraduate students. This means that the wide adoption of the I4.0 systems and related technologies is dependent on the efficient implementation of lifelong learning and training initiatives that address these challenges. Having this in mind, this paper describes the implementation of a series of short learning modules and hackathons that relies on a strong hands-on practical experimentation, regarding the upskilling in emergent ICT technologies, particularly focusing on IoT, mobile robotics and Multi-agent Systems. The preliminary efforts contributed to qualify undergraduate students and active professionals in disruptive ICT, with the attendees' feedback illustrating the importance of these kind of short and handson learning modules to address towards the continuous demands associated to the digital transformation.