NPR's Planet Money has been running a series of podcasts that questions whether this process will continue to hold true in the future. The first podcast examines the Luddites ("When Luddites Attack"), who were English textile workers who protested against newly developed labour-economizing technologies in the early 19th-century. This is followed by podcasts that (1) pit humans against machines in a series of different tasks ("Humans vs. Robots"), (2) examine when machines and people work together ("The Machine Comes to Town") and (3) tells how robots are (possibly) reinventing the restaurant business ("I, Waiter"). The next podcast is a fictional story explores what happens when all the jobs go away ("The Last Job"), while the last examines whether it really is different this time ("This is the End").
All of these podcasts can be listened to or downloaded from the "Planet Money" website (or iTunes). There is also a great series of graphs that capture how machines create and destroy jobs ("How Machines Destroy (And Create!) Jobs, In 4 Graphs").