If Tom Petty wrote a song about the the future workplace it might be called Freestyling,
“now I’m free…freestyling.”

In Average is Over, Tyler Cowen compares freestyle chess to how people might work in the future.

Freestyle chess is a type of chess where players use computers and other people to support their decisions in making chess moves. Freestyle chess teams are the most difficult to beat.

Collaborating with people and using tools to get the job done – sound familiar?

Complicated vs Complex Work

Harold Jarche writes frequently about how automation is replacing routine work in complicated environments. If tasks can be automated, they will be.

If humans are adding no value to tasks, they won’t be part of this work and we should expect the rate of automation to get even faster because we are in the second half of the chess board.

This doesn’t mean all work will be replaced by automation (machines), it means that people will add the most value to work in complex environments.

A simple example of complicated vs complex work is sending a rocket to the moon (complicated) and raising a child (complex). Take a moment to think about the differences of both of these tasks.

As Harold says “the future is complex, implicit and intangible.”

In the future, people who will be most successful in complex environments will be those that can work well with smart machines. There are other factors but in this post I’m focusing on working with smart machines.

Cowen says that, “If you and your skills are a complement to the computer, your wage and labor market prospects are likely to be cheery. If your skills do not complement the computer, you may want to address that mismatch.”

Freestyle Work

Merriam-Webster defines freestyle as “a competition (such as a swimming race) in which the competitors are allowed to use different styles or methods.” There is freestyle skiing, dancing, rapping, swimming, etc.

I think were also seeing “freestyle working” and this trend will continue.

Complex environments are ripe for freestyle work. In freestyle, there are no repeatable processes. It’s an open and emergent environment.

If something can be repeated or figured out, it will be automated and become complicated or simple work.

Cowen says that people who have the skill set to master freestyle chess will be the type of people most valued in the coming workplace and makes a few key points:

  • Human and computer teams are the best teams
  • The person working with the smart machine doesn’t have to be an expert in the task
  • Knowing one’s limit is more important that it used to be

Those that train with and learn from machines will overcome machine deficiencies. Smart machines often provide us with suggestions but we must decide if we should accept or override these suggestions.  Cowen uses GPS as an example that most people can relate to in their daily lives.

Have you ever used GPS and not driven in the direction suggested because it was either not possible or you know that it’s the wrong way? Below is a funny example of this from Michael Scott.


Bring Your Own Everything (BYOE)

BYOE makes freestyle work easier and may expedite the trend. People are coming to the workplace with their own tools and networks helping them solve problems and create opportunities. They still have to follow basic workplace rules (similar to following chess rules) but there is more flexibility and less control for how people work.

Bring Your Own Everything













What Do You Think?

  • Will the future of work be more freestyle?
  • What are some examples of freestyle in the workplace?
  • What are roles where human skills complement (add value to) machines today?



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