Dispatch 17 — May 07, 2021


At various points over the last few years, I’ve used some combination of “generalist,” “synthesist,” and “curator” in my Twitter bio and elsewhere. It’s only recently that I realized they can also be seen almost as steps in a process: look at a broad landscape of topics, synthesize what you see, pick the most important. I like the term generalist, it’s one of the best descriptions of my career(s) and also a good representation of something I see as vital: being able to understand different domains and translate between them.

Although generalist is the term I tend to settle on, there are a number of other adjacent ones in use. The first I heard was T-shaped people which, as imperfect as it is, I’ve been attached to and referring to time and again in various discussions. There’s also Key-shaped, Square-shaped, and The Neo-Generalist. It also ends up representing something that’s too often circling in my mind: the space between the value of a generalist, and how people “on the other side” receive this type of profile and don’t often integrate it in their decisions.

With no distinct conclusion attaching them together, here are a few things that I’ve noticed recently. I opened the comments down below, I’d be curious to see if you have something to add.


Over the last few weeks, I’ve heard of generalist a few times on the Near Future Laboratory podcast. I also had a quick chat with Julian (who hosts the podcast) about another topic, yet we also ended up on the challenges of being generalists. Then I was listening to an episode of Jeffrey Veen’s podcast, The wonder and rigour of the creative process and the guest, Natalie Nixon, mentioned that many people get creativity wrung out of them in school even though a popular profile for the effective worker in coming years proposes creative people being multi-faceted transdisciplinarians (Nixon uses “polymath,” which I consider a different thing). That’s a common trope around discussions of the future of work which, whether it proves correct or not, certainly points to what people want or expect to come about.

A couple of weeks ago I attended the online launch of The Billion Seconds Institute where every founding member took thirty seconds to introduce themselves and someone noticed that a lot of us were saying “at the intersection of.” Which isn’t necessarily the same thing as generalist but definitely pretty close in spirit.

So a lot of people—often working in certain specific areas like tech, some form of creative, or indie consultancy—see themselves as hybrids of multiple disciplines. But that’s not usually what job listings or requests for proposals are looking for. Sure, they might list a bunch of things having to do with design, alongside a bunch of others having to do with frontend developers, to give one example, but that usually doesn’t mean they want an hybrid for the value of straddling two practices. They’re just looking for one person to do two jobs.

Many deciders, team leaders, or product managers will emphasize the importance of communication between teams, the great value of varied perspectives, and getting a mixed group of people around the table. They’ll praise team members for being the glue or the cement, the more fluid connectors between the “bricks” of specialists. But they usually leave that to emerge and rarely look to hire for that role, or ask for someone to fill it when outsourcing to an external team.

In other words, lots of people see themselves as generalists, whether they use the word or not, and lots of people realize the value of these interstitial roles but not many brag about it, and not many hire for it.

Nitch, neech, niche

Now I look at the “creator economy” (I’m not a fan of the term but it’s still way better than “passion economy” so I’ll stick with the former) and I’m starting to think that we see roughly the same phenomenon. I’m pretty sure if you look at all the top YouTubers, Patreoners, Substackists, sovereign writers, and other independent producers of content and ideas, most of them did not study in the field they are creating in, and a lot of them have had a diverse career. There’s even a lot of them who say they are “at the intersection of.”

But. Most of them have also “niched” themselves in a pretty narrow space. Climate change, US politics, right-wing US politics, technology (usually meaning Silicon Valley), platforms, monopolies, China, strategy, etc. Most lists of tips you can find about growing a publication or micro-media and finding “1000 true fans” will say at some point “find your niche,” “you need a niche,” “it’s important to know what your niche is,” or some variation.

Which seems to lead to a similar conclusion as generalists: that more and more people value a multi-domain “hyphenated” career, but when it’s time to pay someone, by salary, contract, or patronage, they need a clear bucket to assign those dollars to.

Disclaimer: Sentiers is not that niched and I’m trying to grow readership so yes, the above observation is probably due to some annoyance on my part but I still see something in that trend of “niching” vs revenue.

Specialized generalists

Is there a word for someone who sometimes makes you cringe and other times you think comes up with super smart stuff? I don’t know, but Tim Ferriss is such a person for me. In his short video on whether you should specialize or be a generalist, he says he often gets asked the question, and I quite liked his answer: you should be a “specialized generalist.”

Combine two skills that are valuable but even more rare and therefore more valuable together. Like a computer science degree and a law degree, or extreme knowledge of finance or mathematics plus public speaking. […]

You’re not dabbling as a dilettante in a million things and never going a mile-deep, but you are spreading yourself across multiple skills that are rarely combined and can be very effectively combined.

He proposes these three skills as “easy” add-ons to a deep expertise.

I would encourage you to consider public speaking, writing, and negotiating to be three very easy add-ons or multipliers for whatever your core skill or skills might be. Those will give you an immediate competitive advantage.

I think those are solid recommendations, but his more general point also reminds me of the key-shaped profile mentioned at the beginning: more than one deep domains of knowledge and experience, joined by familiarity with a shallower but much broader set of topics.

In my case for example, I think the value I currently bring is linked in part to this broad knowledge and outlook, but most recent work has been anchored to my much deeper experience in the “stack” of web development skills and/or with the publishing stack and/or curation and knowledge management. Those anchors seem to be what people are hooked by (pun intended).


Until I listened to Ferriss’ video, I wanted to also write about facilitation here because I feel it fits with the work or potential work of many generalists. I now see that it can be seen as one of those multipliers he talks about.

A facilitator is a person who helps a group of people to work together better, understand their common objectives, and plan how to achieve these objectives, during meetings or discussions. In doing so, the facilitator remains “neutral”, meaning they do not take a particular position in the discussion. Some facilitator tools will try to assist the group in achieving a consensus on any disagreements that preexist or emerge in the meeting so that it has a solid basis for future action. (Wikipedia’s definition.)

Often times, when there’s a discussion about generalists, the words “bridge” or “translator” will pop-up. Going back to my days as a frontend web developer again, being able to talk with (and be interested in) designers, backend developers, the client, the SEO person, etc. often proved a very valuable skill, because too many of them had a narrow focus (sorry for the generalization) and, sometimes literally, couldn’t understand each other. This bridging comes with broader interests and curiosity, but skills of facilitation seem like a great way to turn that up a few notches.

Sadly, I didn’t properly take note of these instances and couldn’t find strong enough links to include here, but in the last couple of years I’ve read that managers need to be facilitators for their teams, teachers need to be facilitators to their students, and I’ve seen the actual role of facilitator being mentioned more often.

Perhaps the effective generalist facilitates between disciplines? Perhaps the skills of facilitation are the fourth great multiplier?

As I said, I don’t have a great unifying insight to fuse these things together, they are adjacent topics I’m pondering. Hit reply or head for the comments if something clicked for you.