The Future of Generalist Work

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

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

Every. Single. One. of the startups that I've worked with have some

co-founder (or early team) dynamic that implicitly shapes their lasting culture.

These practices may be well-known and honored, or they may be hard-coded yet unspoken (like the pie in my story above). Either way, they are a part of the company’s DNA — its nature.

As an Ops Leader,... See more

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

Generalists, with their diverse skills, adaptability, and ethical awareness, are at the vanguard of this new epoch. They aren’t just visionaries but also implementers, merging AI-generated efficiency with human creativity and ethical discernment.

While frameworks can offer valuable perspectives and guide decision-making, rigid adherence to them can lead to tunnel vision and unhelpful outcomes. Successful decision-making often requires a blend of framework-guided analysis and intuitive judgment, where the needs of both the business and the customer are carefully considered.

Generalists have the advantage of interdisciplinary knowledge, which fosters creativity and a firmer understanding of how the world works. They have a better overall perspective and can generally perform second-order thinking in a wider range of situations than the specialist can.

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

The tools that are available to each of us are so powerful, so varied and so complex that even the free ones are ignored or misunderstood. We’re too busy doing work to get much done.

And so we end up with the convenient and sexy tools (like the smartphone you might be reading this on) and fail to do the few hours or days of training we might need to... See more