It might seem that humans no longer have anything to contribute to the game of chess. But the invention of freestyle chess tournaments shows how far this is from the truth. In these events, teams can include any combination of human and digital players. The key insight from freestyle chess is that people and computers don’t approach the task the same way. This distinction is a valid and important one, adding up a column of numbers is totally routine and by now totally automated, but here again the boundary between the two task categories is not always obvious. Very few people would have considered playing chess a routine task half a century ago. In fact, it was considered one of the highest expressions of human ability. We’ve never seen a truly creative machine, or an entrepreneurial one, or an innovative one. Programs that can write clean prose are amazing achievements, but we’ve not yet seen one that can figure out what to write about next. We’ve also never seen software that could create good software. These activities have one thing in common, ideation, or coming up with new ideas or concepts. To be more precise, we should probably say good new ideas or concepts, since computers can easily be programmed to generate new combinations of preexisting elements like words. Ideation in its many forms is an area today where humans have a comparative advantage over machines. The boundary between uniquely human creativity and machine capabilities continues to change. After time working with leading technologists and watching one bastion of human uniqueness after another fall before the inexorable onslaught of innovation, it’s becoming harder to have confidence that any given task will be indefinitely resistant to automation. That means people will mean people will need to be more adaptable and flexible in their career aspirations, ready to move on from areas that become subject to automation, and seize new opportunities where machines complement and argument human capabilities.