A timeline of (possible, fascinating) future events from a (wide) variety of perspectives

Back in 2016, New York Magazine tapped a bunch of people from a variety of backgrounds and asked them to imagine events that might take place over the next eight years; as with all futuristic exercises, it's less interesting as a predictive exercise and much more interesting as a diagnostic one, a snapshot of the hopes and dreams for the coming years on the cusp of the 2016 election.

Now, in the final months of 2019, New York Magazine has repeated the exercise with new contributors (including me). As with the 2016 edition, this speculative timeline's strength is in its fears and aspirations, not its notional prognostications. The magazine did a good job of gathering contributions from a wide range of backgrounds and situations (for example, prison journalist John J. Lennon speculates on what his life might be like in September 2019, when he imagines that he might get parole for the murder he committed in 2001).

Here's my contribution, about the paths we might take to breaking up Big Tech:

Today, anyone who hopes to restore the competitive, pluralistic, decentralized internet has to overcome not just the tech companies commanding market dominance but also the political influence Big Tech can buy with its monopoly profits. This can seem hopeless: We have to weaken Big Techs profits in order to rob it of political power, but while it wields that political power, its hard to imagine ever eroding those profits.

How then might we arrive at a 2029 where the internet is restored to its unwalled glory and chaos?