My thinking here started, as it often does, with a Justin Gage tweet.

A few weeks ago Justin tweeted that “be a generalist” was the worst piece of career advice he’s ever gotten. Good or bad, it’s at least broadly accepted as a Smart Take to have. There are numerous books extolling the virtues of being a generalist. I think it’s terrible advice... generally speaking ;)

justin g. @itunpredictable

thinking about the worst advice i've gotten in my (short) career, "being a generalist" is probably the most destructive thing i was told. actively set me back my a couple of years

January 4th 2021

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NB: this is confined to non-technical folks (“biz side”) at startups.

TL;DR when people describe themselves as “generalists” what they often mean is “overall smart person with/seeking high status but unspecific job.” That’s not helpful. But founders/startups DO need executors, some of whom have general skill sets rather than highly specialized or technical ones.

The advice to “be a generalist” is the close cousin of “retain optionality.” It sounds smart and has reasonable parallels elsewhere. You’d never put your whole life savings in a single stock, right?

But keeping all options open whether by avoiding the appearance of specialization or by running from professional “lock in”, has diminishing returns. You’ll wind up treading water and passing on good opportunities for fear of losing your precious optionality.

Being “a generalist” in a generic context doesn’t mean anything. It’s an excuse by people who fancy themselves clever and scrappy enough to do most anything without prior knowledge or experience. So long as “anything” is high status and interesting, that is.

Very often, the Clever Generalist is a recent grad (BA or MBA) looking for Chief of Staff, Biz Ops, or Strategy roles, usually sprinkled with a “bit of product” or “growth but not sales” for good measure.

They don’t necessarily have specific qualifications but they know they’re smart and, more importantly, insightful enough to slot right in and contribute Big Ideas. FP&A or customer service or coordinating the new lease or cold calling prospects or re-stocking the fridge is a waste of their talents. They are “big picture” people looking for big picture work. 

We all know these people. Some of us are or have been them. I certainly have been.

However, in specific contexts and with the right attitude, generalists can be essential: when either 1) resources are so tight that you need people to pick up the slack and fill holes or 2) orgs become big and specialized enough that they need to be forced into cohesion/translated across.

In the first case, the generalist plays janitor and does all the unglamorous things that the CEO has only just herself stopped doing. In the second, the generalist is functionally a project manager, part of the professional managerial class within the company that makes shit work, even if they’re a step or two removed from the doing of said shit.

There’s an animating purpose for the role and a skill set/domain expertise required to do it well. You can’t just waltz in and declare yourself “capable of all things, generally.”

If I left VC, I’d likely work in a “generalist” role. I can do a bit of corporate finance, sales/BD, recruiting, and brute force operations. I can prioritize and manage politics well. These tools have some generalizable usefulness but are *specific* skills built up over particular experience and applicable (at least by me) in only a narrow range of circumstances.

I’d probably have some vague title like BD, Biz Ops, corp dev, GM, etc. Much of my job would be project management. Karl Yang has more on that if you’re interested.

Jon Coffey, a noted MBA and Generally Clever Person, put it like this: people often conflate "cross-functional" and "generalist" but to do most of these jobs you need a specific set of skills and expertise that other people in the organization probably don't have. So find or develop that skill set. Figure out a way to be uniquely, and specifically valuable.

You can have generalist knowledge or a generalist skill set — not both.

Assess opportunities by your ability to make an impact with what you have, whatever that may be. And if all you have is work ethic and smarts, roll with that until you can develop something more.

Start as operations associate, BDR, or finance manager and just fucking crush it. Move up within that org chart. Take on more responsibility and find new arenas in which to apply that skillset and domain expertise.

Being smart and hardworking is not enough on its own. Assuming otherwise (and assuming that people will just recognize your innate brilliance) is a short path to disappointment when there is real, if unglamorous, work to be done.

So don’t be a generalist if you can help it. Build a skillset and put it to work.

Many thanks to Jon Coffey for his feedback and edits on this.