The Future of Generalist Work

When you make changes in your life, especially when learning new skill sets, you’ll have to cross a moat of low status—a period where you are bad at the thing or fail to know things that are obvious to other people.

It’s called a moat both because you can’t just leap to the other side and because anyone who can cross it has a real advantage.... See more

We’ve created this world where left brain people are free to act on their fairly narrow rational behaviors without being policed. Whereas the burden of proof demanded of a creative act is literally 20 times greater. – Rory Sutherland

If consumer behavior is evolving as a result of technology, businesses either compete to get ahead of it, they perpetually react to it, or they belittle it. One of the most problematic aspects around digital maturity is that technology is both part of the solution and also part of the problem.

Today, management is a skill that only a select few know because it is expensive to train managers: You need to give them a team of humans to practice on. But AI is cheap enough that tomorrow, everyone will have the chance to be a manager—and that will significantly increase the creative potential of every human being.

It will be on our society as a... See more

Emotional labor is the opposite of the industrial economy’s task-based, measured output. Even if we don’t dig ditches, the offer for a certain kind of work was: Process this pile of papers and we don’t care whether you like (or pretend to like) your job. The labor is the easily measured stuff.

But AI and mechanization have turned this sort of task... See more

Top tier executive assistants are great at many things but have critical core operational tasks and simply don’t have the wide strategic business context required for CoS-style work.

These passion job organizations are burnout factories. Every year, a new crop of eager recruits comes in, grateful to have landed a job doing work “they love” — and every year, a significant percentage of the existing workforce churns out. Some have been there that single year, others for five. They leave not because they’re not good “fits” for the... See more

My aha moment of the value of first principles thinking was when I was at Dropbox. We would hire a ton of really smart people that had never done sales and had them do sales. There are a lot of disadvantages to that, but I do think it led to a ton of innovation. That's how we got our very innovative go-to market motions because a lot of those... See more

And what you see internally is what I'll say is razor-sharp focus on reducing cycle time and bias to action and how do we reduce cycle time. I think it's basically the core of it culturally to me is getting people to think about smaller units of time for decision making. It seems obvious but I think you really have to reinforce it culturally. So... See more