In the 2000s the challenges were mostly about the battle against Microsoft and its proxies. So there was a lot of emphasis on the details of lawyering work. Plus there was the crowdsourcing of the GPL version 3 license.
In the 2010s there has been less focus on lawyering and more on diversification to include people who are not bearded 20-something male computer science graduates from ivy league universities. Obviously more needs to be done, but watching the recent NextCloud conference I think we're mostly on the right trajectory.
Where do I think the Free Software movement should go in the 2020s?
What I'd like to see would be a campaign to create a worldwide guild of public coders. Maybe it could be called the Software Commons Guild or something like that. As an umbrella crafting organization the guild could have significant leverage against the Surveillance Capital companies who currently dominate the internet. Companies like Google, Facebook and increasingly also Microsoft rely on a lot of Free Software, and the withdrawal of support by a large public coding guild would impact their operations at a fundamental level.
Existing mentoring would be replaced by apprenticeships, and there could be new licenses which are granted once a company meets the guild's standards. So for example, companies might only be granted a license to use certain public code if they pass technical production process and ethical criteria for use of technology defined by the guild.
This of course would create yet another power structure, but at this point I think that's what's needed. Individual software engineers, no matter how clever or how ethical, simply don't have leverage against the megacorps - as evidenced by the recent Google walkout and its subsequent consequences, or attempts to unionize in other companies such as Kickstarter. Collectively as a guild perhaps they might be more successful and begin to turn around the numerous problems of the industry.