My story with Free Open Source software started in 2004: founding the SpagoWorld initiative; networking with international communities: OW2, Eclipse, OSI. A long journey launching initiatives, creating projects, building communities, meeting people with diverse attitudes. A lot of lessons learned. What’s next? This speech will introduce a look at future prospects and challenges of free software in the era of digital transformation, aiming at keeping the spirit of the ground values of open source alive over time. In 2010 I wrote the paper “Which open source software for the current decade? Five questions for the future”. It’s now time to answer to its final question: “Which approaches and real opportunities do we need to adopt in order to lead the business and technological innovation towards a new knowledge-intensive way of producing and living?”. The data-driven culture means a change of mindset and behaviors. TRUST, one of the free open source key-words, is part of the answer: progress is not possible without trust, in the digital world. And when we will not have choices, we’ll must be prepared to see a TRADE-OFF. Here the role of free open source communities comes. Ethos and pathos embraced by transparency. A lot to do and spread for open source communities again!