The Future of Generalist Work

This has been the core question I’ve sat with for the last decade—how to balance money and meaning on the entrepreneurial path. And there are three archetypal ways that I’ve seen people approach the question:

• The deferred life plan


• Being bivocational


• Choosing to integrate

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

That’s what -1 to 0 feels like: messy, confusing—squiggly. The hardest part is escaping. What ultimately leads you out of the mess is conviction, a state you must build incrementally and internally. And conviction and certainty are not the same.

For many people, -1 to 0 is also about deciding how you want to work. In a startup? In a big team? As a... 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

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.

We live in a knowledge economy. What you know—and your ability to bring it to bear in any given circumstance—is what creates economic value for you. This was primarily driven by the advent of personal computers and the internet, starting in the 1970s and accelerating through today.

But what happens when that very skill—knowing and utilizing 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