Stuck in Generalist Hell

They say you should write about the question that’s burning in your mind. So here’s mine: is there a generalist hell? And am I stuck in it?

When saying the word generalist, you’ll get one of two reactions. The first is “jack of all trades, master of none,” a negative take on generalism defended, for example, by Jeff Atwood.

This view seems to circulate the most in techie/engineering rings. Just yesterday I was browsing Hacker News when I came across a comment that went “being a generalist is worse than useless — i would not advise it.” That’s just one example.

The other view is Naval Ravikant’s, mimicking Heinlein:

A human being should be able to change a diaper, plan an invasion, butcher a hog, conn a ship, design a building, write a sonnet, balance accounts, build a wall, […] program a computer, cook a tasty meal, fight efficiently, die gallantly. Specialization is for insects.

Robert Heinlein

So which is it?

Readers of my blog and people who know me know: I am undoubtedly a generalist. In this blog alone I’ve talked about topics ranging from knowledge management to typographyhabitswritingenergystartupsproductivitytypesetting, and more. Outside of the blog I’ve sold my own software, I’ve taken up marketing and sales roles, I’m the sole technical writer and QA guy at my workplace. I studied CS in high school, then got a degree in a social science. I write blog posts, did voice acting, learned and taught three languages, and wrote academic papers about Byzantine robots.1

Is this good? Maybe. There are some advantages.

In the workplace, it’s harder for people to play on your ignorance. You know approximately how long something takes to make, and you understand, at a basic level, how it works. You know enough to know whether others are doing their job or not.

Being a generalist is nearly a requirement to be an entrepreneur. You have to know how to build, and you have to know how to sell, at the minimum. And you have to know whether the people you hired are actually competent, even though you don’t have their mastery.

So why am I talking about generalist hell?

Well, for example, I’m good at marketing and sales. But if my company wanted to, they could hire a specialist who could do it better. Same thing for QA, technical writing, management, and everything else I do. My blog is no different: while I write about all these different things, you can find people who write about each specific topic better than me.

When you’re a generalist, for anything you do, there is someone who can do it better. You’re not good enough to be a full-time developer. Or a QA engineer, technical writer, blogger, academic, marketer, what have you. You’re good enough to understand it all, but not good enough to have achieved mastery in any one of them.

When applying for jobs, generalist hell comes especially alive. Being a generalist automatically excludes you from applying to any company that’s not incredibly small. The last thing a medium to large company needs is someone who can do “a bit of everything.” True, there is an advantage to showing up to smaller companies. After all you’re a person who takes the place of 4-5 others, so the savings are considerable. Eventually, though, they will outgrow you.

It seems I’m stuck between a rock and a hard place. Either I buckle down and master a skill or I become an entrepreneur. What should I do? This is the question burning in my mind.

  1. (email me for the PDF)