Are you a grinder or philosopher?

"That’s the most important thing you have to understand about the Big-Three consulting world: it selects for intelligent, high-energy grinders, not snowflake philosophers driven by foundational curiosities. People who set out early in life to win the game as it is presented to them, rather than question, subvert, or change it. Which is not ipso facto a bad thing. If the game presented to such people is a good one, they will play it well, and a good time will be had by all. The world runs on grinders. When it runs at all."

Venkatesh Rao, The Art of Gig, Volume 1: Foundations

I consider myself to be a lazy guy.

I'm not lazy in the sense that I don't do anything, but rather, lazy in the sense that I have a very difficult time forcing myself to do things I don't want to do.

This includes most activities that come with a job.

I'm not a grinder.

A grinder is easily identifiable in high school. Always studying, sort of anxious, and obsessed with perfect grades and getting into top colleges.

They're found in many top consulting firms, investment banks, etc. Basically any sort of prestige profession or company.

They can keep doing the work even if they don't inherently like it, which serves them well in the professional world.

I consider myself to be a "philosopher," both in the silly snowflake way where I think too highly of my own ideas, but also in the important way in which I think a lot about how the world works and how I want to fit in it.

The philosopher is not suited to play the corporate game. He will get fired or quit. Which is why I went 1099.

"Those miscast on the grinder frontlines, or with too much maladaptive talent for the devalued kinds of thinking, tend to burn out early and drop out. They typically don’t last long enough to make partner or execute a smart sideways shift into a VP role on the client side. So there is a strong adverse selection process at work here. At the tops of these firms, there is not just a disciplined tendency to stay away from doctrinal matters, but a systematic functional weakness in the capacity to think about them in the first place."

Venkatesh Rao, The Art of Gig, Volume 1: Foundations

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If you're not a grinder, and you're stuck at a big company with a strong corporate culture, you should find something else to do.

1099 is a strong option, but also finding a smaller company or even a niche gig within a bigger company is a better path for you. Then pursue side projects that engage your brains and interests.

No judgements, but if you're lying to yourself about which category you fall into, you're going to make yourself miserable.

Want the full playbook? Check out Going 1099.