A Generalist’s World - How I found My Community

Spice shop

I’ve always had a hard time settling on a single specialty that I could see myself dedicating my full time and attention to. And so naturally, my career hasn’t looked like that of most of my peers.

In fact, I never even had interest to become a specialist committed to just one thing.

For me, I’ve always been energized by the effect that doing many interesting and diverse things has had on me. Variety is, after all, the spice of life. And I’m running a little spice shop at this point ???????There’s just too much great stuff in the world to be interested in, and I have never been the type of person who wanted to choose. So I’ve simply always kept myself involved in a LOT of different disciplines and fields of study.

But the world hasn’t historically been designed for generalists. It’s always been designed for people who pick one specialty and dedicate themselves fully to it - people with deep knowledge in a single field. And fair enough, this was a function of the way the world has worked until just very recently.

Adam Smith and the division of labour

I still remember like it was yesterday; 25 years ago in my high school ‘Intro to Macroeconomics’ class, Mr. Gilmore (an old-timer, and one of my all-time favourite teachers) spent a good chunk of a semester teaching about Adam Smith, one of the pioneering economic thinkers. One of Adam Smith’s several major contributions to the study of economics, aside from ‘The Invisible Hand’, was the concept of division of labour and specialization. In short strokes; dividing work into specific roles, with each person having narrower responsibilities and more focused efforts, therefore able to improve and specialize in one specific skill and yield higher outputs.

Until Adam Smith, the world produced as artisans. A shoe maker learned the craft of shoemaking and made shoes, start to finish. Not the most efficient process, but it’s what existed. But Smith saw specialization as an alternative to the way things had been done since, well, forever. He saw it as a way to maximize possible production output when leveraged within the context of other specialists performing other highly-specific functions.

With specialization, a lace-weaver would weave shoe laces, a sole-maker would form shoe soles, a pattern-drafter would draft the leather shapes for the upper and hand those off to a cutter, who would then hand off to a closer, who would assemble all parts together. Each person a highly-trained specialist in their own narrow function.

Of course, those who started and managed businesses have always been generalists, by necessity, but more on founders later. Back to specialization…

Under these conditions, those five people could produce several times the output of shoes in a day or a week than five shoe makers could possibly produce if they were each performing the entire process.

This logic made perfect sense, and continued to prove its validity as a working model over the last few hundred years. Until very recently, that is.

The world is now fundamentally changing, and faster than any of us might be prepared for. Recent advances in technology have turned Adam Smith’s concept of specialization on its head, and the economic thinkers of the world are now beginning to recognize the virtues of those that have cross-functional capabilities. Artificial intelligence is quickly rendering many specialist jobs obsolete, forcing a necessary shift in the future of work.

The underlying logic that drove the validity of the division of labour and specialization concepts applies less and less as AI technology improves and grows. It’s like the Industrial Revolution all over again, with many of the very same new challenges being presented, but in different ways and within a different context. If a machine can perform a specific given task (and perform it better, faster and with fewer errors than a human), then our value as people shifts, in a fundamental way, away from the performing of the task and over to the management of the technology.

And these new technology management roles require an entirely different set of skills - a set that is decidedly dependent upon one’s ability to bridge a multitude of inputs and connect dots, often in a non-linear way, synthesize information and apply it in diverse contexts… basically, to figure shit out. And figuring shit out is a decidedly generalist sort of skill that draws on a lot of different sources, skills and capabilities. It’s also a decidedly human gift (for now, anyway).

Now, this is not to say that generalists own the future, and specialists are doomed. But this shift will mean that we, as a population, will need to learn to make the most of the way that generalists, specialists and technology can work together, in as productive a way as is possible.

According to Greg Isenberg , generalists matter “because managing AI agents and human talent is high leverage.”

But the world of work isn’t very well-prepared to usher in the era of the generalist, as it’s historically placed value in those that have fit the specialist mould - and for all the logical, right reasons, granted. So generalists like myself are still having a hard time defining our value, telling our stories, communicating our narratives and just generally making the most of our differently-shaped potential!

Enter; Generalist World ?? . One of the very few - but highly active and influential - community groups leading the charge and championing the new wave of industry awareness and understanding about generalists as a key segment of the workforce.

Generalist World

Led by Milly Tamati and a small group of multi-talented, generalist women, GW is a powerhouse community-based business that’s not just impacting the lives of their community members around the world, but they are writing the book, so to speak, that’s defining generalist value in today’s (and tomorrow’s) world of work.

When I originally came across this community, it felt like I was arriving home, and discovering - for the first time - that there are more people like me, with the very same questions, challenges and gifts as me.

Through a multi-layered stack of tools and platforms, including a very heavily-trafficked Slack community, a collection of permacontent in Notion, a continuous stream of exploratory essays by world-class thinkers and constant live virtual events and workshops, GW provides a metric ton of deep, thoughtful, insightful and hugely-valuable resources that are responsible for making this the single most active online community I’ve ever been a part of.

They even do this brilliant thing that they call a ‘hot seat’; an hour-long virtual webinar-style event focused on one individual GW community member. During a hot seat, the GW team and members of the GW community gather together to focus on discussing and answering the challenges of the community member sitting in the hot seat. It’s pretty fantastic! Like having a personal advisory board. Every community member can schedule their time in the hot seat if/when they have a challenge to attack and want the synergistic power of bringing many heads together to focus on them, and only them, for an hour. They prepare a brief outlining their goals, challenges, doubts, dreams and questions related to their business or their career path. Questions get asked, ideas fly around from one hot seat attendee to another, experiences get shared, insights get offered up, and breakthroughs happen. I was recently in the hot seat myself, and it was an invaluable experience, one that was alone worth the price of admission (ie. the annual GW community membership fee).

Through their diligent work, GW is helping generalists to figure out how to develop, hone and leverage generalist superpowers to:

• manage and grow their businesses
• demonstrate their value in a world that doesn’t yet understand generalists all that well
• find the language to tell their stories
• discover previously-unknown career paths
• land incredible, high-level positions in which their generalist gifts will be celebrated and appreciated
• find balance and fulfillment in their work (and lives outside of work)

If, while reading this, you’re getting the distinct feeling that you too may be a generalist, then this might just be a marked moment in your personal development journey. Why? Because now you know it’s a thing! A real thing that exists, and you’re not alone! And best of all, it’s a super valuable gift that you can get help honing and channeling in an effort to move in the direction of your personal and professional goals, whatever those may be. Hell, maybe you’ve never really been able to pin down your direction for personal or professional goals, and armed with the important initial knowledge that being a generalist is in fact a thing, you’ll finally be able to gain some direction! Well, if your spidey sense is tingling from this, I’d highly recommend checking out Generalist World ?? .

***Important to note that I’m not sponsored by, or connected with, Generalist World in any way other than being a happy, paying member of their community. In fact, I didn’t mention to them that I’d be writing this piece ?? Everything I’ve said about GW here is just a function of me being really positively-impacted by the fact that they exist, and do such a good job with it.

If you’d like to dig a little bit deeper, I’d highly suggest watching this video by one of my absolute favourite interviewers, Arvid Kahl of the Bootstrapped Founder podcast. In it, he talks with Milly, GW’s aforementioned founder, and together, they kick up a bunch of dust on some incredibly interesting topics, all revolving around the idea of generalists :)

Comb-shaped people & flexible T-shaped people

As Milly explains in her interview with Arvid, the challenges we’re presented with in today’s world are so much more complex and messy than they’ve ever been in the past, which is precisely why generalist stock is growing. And in order to help illustrate where the value comes from, Arvid mentions the various figurative people-shapes that are used to help define the types of folks out there in the world of work.

In general, the width of the shape denotes the breadth of experience, knowledge and sectors, while the height of the shape denotes the degree of expertise. And while there are new shapes invented by thought-leaders all the time, let’s take a look at a few of them;

I-shaped people: Those with deep knowledge and expertise in one specific area, without necessarily having broad interdisciplinary knowledge or skills. The quintessential specialist.

T-shaped people: Those with some shallow knowledge in a broad range of areas, but deep expertise in one specific area.

V-shaped people: Those with deep knowledge in one area, but gradually-broadening expertise in adjacent areas.

Pi-shaped people (as in the Greek letter Π?/ π): Those with shallow knowledge in a broad range of areas, and 2 specific areas of deep expertise.

M-shaped & comb-shaped people: Those with shallow knowledge in a broad range of areas, and a multitude of areas of deep expertise.

Then there are X-shaped people, square-shaped people, tree-shaped people, spider or octopus people… the list goes on and gets wilder and wackier the more you dig.

Granted, the fancier you get with these shapes, the more convoluted this whole people-shapes exercise becomes. But the underlying point is really to graph breadth on one axis against depth on the other… and to visualize it in such a way that it helps us understand our strengths and how we can leverage them to make the most of what we work on - and who we work with.

So which shapes describe generalists? Well, comb-shaped people certainly embody a lot of what most generalists bring to the table. But Arvid artfully offers up a simple, yet more visually-dynamic people-shape of his own in order to attempt a better understanding of generalists; He posits that a generalist is just someone who’s capable of moving the trunk of the T-shape around into different areas of expertise in a flexible way - Flexible T-shaped people.

One of the reasons I think the flexible T-shape is a great representation of a generalist is that its shape doesn’t assume that the person already embodies all of the prongs of a comb. Rather, it celebrates the unique gift that generalists usually have, the gift of curiosity. Learning is indeed at the core of the generalist profile. When a generalist comes across a new challenge or gets inspired by a new opportunity, they get energized by the prospect and process of exploring and going deep on that new area of expertise. The openness and ability to flexibly move that trunk around is a superpower in and of itself, and in my opinion is the defining piece in the generalist people-shapes exercise.

This flexible T-shape really resonated with me, and feels like a pretty solid framework for visualizing the dynamics of my own breadth and depth of knowledge and expertise. So for that, Arvid, I thank you!

But to take the people-shapes discussion one step further - to where it becomes meaningful and actionable for organizations; a team that’s going to be truly stellar in today’s world, and moving into tomorrow, is going to be one that has a healthy mixed salad of all of the people-shapes.

As Milly said, today’s challenges are more complex and messy than ever, and in order for an organization to cope and thrive, it’s imperative to have a well-curated, and continuously-revisited, mix of flexible T-shaped people and comb-shaped-people connecting the dots across teams of I-shaped people, T-shaped-people and V-shaped people.

Importantly, those who will be able to effectively manage that mixed salad of people-shapes are necessarily the ones with cross-functional breadth and meaningful depth of expertise in all of the areas relevant to the people in the salad. That is to say; generalists.

Language: Some attempts at defining generalists

This seems to be the biggest challenge that generalists have; figuring out just how to describe their value and communicate it to those they might want to work with. I’ve personally struggled with this quite a bit, and so I naturally started to record all of the useful language that I come across into a handy spot in my Notion workspace. Every time I read anything that offers another way to describe generalists or generalist value, I capture it.

There is, of course, no single perfect way to put this complex idea into words, but the more options we have - the more ingredients we have in this fridge - the better equipped we can all be when it comes time to cook up an effective description for someone about who we are and why it matters.

Here are a few descriptors that are thrown around online and in the GW community:

• Able to stack multiple areas of expertise and apply knowledge from one area to another in innovative ways
• Resourceful and creative problem-solvers with stacked tool belts
• Non-linear thinkers who connect the dots across domains to expose patterns or opportunities that others don’t see
• The connective tissue that binds together teams, departments and functions across organizations
• Endlessly-curious expert learners
• Empathetic self-starters
• Thrives in levels of ambiguity that others can’t cope with
• Excels in uncharted territory with no map or guidebook
• Cross-functional, multi-disciplinary ability to apply strengths across varied fields and roles
• Able to live both deep in the weeds and 30,000 feet overhead at once
• Flexible and versatile, able to change and adapt to the changing needs of a growing organization or project
• ‘Portfolio careerists’ (open this article in a new tab to dig deeper into this later)
• Neurodiverse thinkers who approach complex problems differently
• ‘Spiky’, resilient, adaptive contributors
• ‘Squiggly’ career path - hence the ???on so many GW member LinkedIn profiles
• Experts in ‘figuring shit out’, especially when others haven’t been able to

But of course, this is just a small sampling of the hundreds of ways I’ve come across that attempt to describe just what it means to be a generalist. And naturally, if you zoom in, there are many sub-segments of generalists, each with their own strengths and particularities. So although our first order of business as generalists is to develop the language that can effectively get our overarching point across, this will likely be the start of a field of study of its own.

A favour: While you’re reading this, if you think of any other great ways to describe the characteristics of a generalist, please go ahead and add them to the comments at the bottom of this article. I’ll share any great additions/ideas/descriptions with the GW community, and together we’ll get closer to explaining this huge idea to the world.

The Conductor, the GC and the GP

Aside from the right language to describe and communicate generalist value, it’s always helpful to use metaphors to do some of the heavy lifting. It only makes sense to employ someone’s pre-existing understanding of one thing, and tie it to another thing that you want to convey to them. A bit of piggybacking ??

?? The Conductor of an orchestra must learn to play all of the instruments - not necessarily to a soloist level, but to a level of being able to effectively conduct each orchestra member, and their respective instrument and part, with meaningful ability and context. A Conductor is indeed an orchestra generalist, connecting the dots across the orchestra, thereby turning their collective work into the resulting symphony.

??? The GC, or General Contractor, of a construction project must learn all relevant trades in order to effectively manage the order and execution of a reno or build. In fact, most really good GCs have years of their own experience across many different individual trades. Much like the orchestra Conductor, a GC is indeed a construction generalist, bridging the work of the framers, plumbers, electricians, drywallers, tapers, tilers, carpenters and painters, ensuring that all is executed in sequence and according to plan.

?? And the GP, or General Practitioner (otherwise known in some places as a Family Doctor), relies on having context and understanding across a wide breadth of medical fields in order to be able to diagnose and then determine which kind of specialist physician a given case should be referred to. Without the GP, patients would likely die from serious, but treatable, conditions, simply because they wouldn’t know who to go to and for what type of treatment. In the same way, a generalist serves to diagnose and direct in a business context.

The classic, quintessential generalist role

Let’s not get too self-important here though, it’s not like we’re inventing anything new… generalists have always existed. As long as civilization has been around, there have been people who started things - communities, groups, initiatives, movements, businesses, shops, teams. And every person who has ever started something and was then responsible for managing it and growing it, had to wear a variety of hats by necessity.

This is why I believe that the classic and quintessential example of a generalist role is: founder.

And it’s why so many generalists end up opting to start their own businesses rather than joining an organization and having to conform to a specialist role that would leave them unfulfilled, and leave the organization with the opportunity cost of forgoing all of that missed generalist value.

Founder is, in my opinion, frankly still the very best role for a generalist today. It’s one that squeezes every last drop of juice of the generalist's value, and is perhaps where an effective generalist can make the biggest overall impact.

But it’s not a realistic or ideal option for everyone, for a variety of possible reasons:

1. Not everyone is cut out to be a founder. Starting something comes along with elements of risk, uncertainty and responsibility that doesn’t appeal to every personality profile.
2. Not everyone has the luxury to start something because of family responsibilities and/or the need for financial stability (something I’ll explore in another article I’m currently writing).
3. As time goes on, there are other opportunities that might be as impactful - or more… let’s explore that;

The changing winds are now broadening our options as generalists, and meaningfully-lucrative opportunities across organizations are starting to gain common acceptance in the world of recruiting. So much so, that we’re at a point where the impact and earning potential of a high-level generalist role in a great organization can represent a net-better opportunity than the prospect of founding and building something new.

Other popular generalist roles

So what else is out there, other than ‘founder’, for a generalist looking for a new adventure?

Here’s a list of some of today’s most notable generalist-aligned roles:

• COO / Operations Manager
• Chief of Staff
• Strategist
• GM
• Product Manager
• Program Manager
• Project Manager
• Brand Manager
• Partner Manager
• People Ops Manager
• Special Projects
• Producer
• AI Prompt Engineer

And increasingly, titles that actually include word ‘Generalist’, like:

• Early Stage Startup Generalist
• Product Marketing Generalist
• Ops Generalist
• GTM Generalist
• HR Generalist
• RevOps Generalist
• UX Design Generalist

Another favour: While you’re reading this, if you think of any other titles that are decidedly generalist-aligned like these are, please go ahead and pop them into the comments at the bottom of this article. Knowing what titles to search for is key to finding generalist opportunities! Who knows, maybe your comment will spark another reader’s search query and a few dominoes later they’ve landed a life-changing generalist position!

Size matters

A sweet spot exists for generalists today in the space between being a founder and joining a large organization, one that quite perfectly leverages the magic that generalists bring to the table. That sweet spot is small, scrappy teams.

Granted, generalists are important members of any size team, and in large organizations can really shine when paired with high-level specialists, in order to help extract maximum value out of those specialist. But generalist shine brightest on small teams where wearing many hats is an innate, and in fact, essential, part of the job description.

As logic dictates, the smaller the team, the more important it is for each member of the team to wear more of the hats. Otherwise, there’s no way to cover all of the functions required to run the business. Therefore, small teams require many - or most - of their members to be generalists on some level. And naturally, as a team grows and each new team member’s role becomes more specific and defined, the opportunities for generalists tend to shift toward only certain roles that require them.

So it only makes sense that looking for a role at a 10, 50 or 100-person company is more likely to yield a successful hire for a generalist than aiming to join a 500, 5,000 or 50,000-person organization - not to mention more likely to yield job satisfaction for the generalist and meaningful results for the team.

Something to think about ??

The future of work

Fine, so we now understand that generalists have value, and we are starting to get an idea of how to describe and channel that value. What now?

Well, a couple of things:

Shifting roles

The fact that you’re awake and alive, reading this article right now, tells me that you are likely aware of the impact that artificial intelligence technology has had, and is having, on our lives. Work, as we know it, is changing so quickly that we’re at the same time scrambling to harness the unprecedented opportunity AI presents, while also scrambling to remain relevant ourselves, as human beings.

So it’s important to recognize that our roles as humans in the workplace is evolving, and there’s no stopping this evolution. As AI progresses and finds its way into literally all imaginable work functions, our role is shifting from doing the work to overseeing and directing the work. This will generate two important results:

1. Generalists will continue to become more and more valuable and important, as our jobs change from connecting and directing the work of specialists to connecting and directing the work of machines.
2. Specialists will be required to expand their breadth, and grow from I-shaped people to at least T-shaped people in order to remain relevant in a world that functions differently than it once did.

Buy-in to the generalist movement

I can envision a future in which organizations, job boards, end even platforms like LinkedIn, define roles based on their associated/required people-shapes, or on their breadth-depth profiles, in some way. A future that doesn’t need communities like Generalist World to be advocating for generalists to be understood, heard or considered. A future that values generalists as much as the past has valued specialists.

This is your moment to plug all of this into your processes and activities managing your organizations, and to start structuring your teams in such a way that takes advantage of this knowledge.

This is your moment to begin using the word ‘generalist’ in your job descriptions, org charts and position titles. And it’s your opportunity to write the next chapter of the future history of business, by innovating new ways to work, new ways to produce and new ways to grow, equipped with this knowledge.

It’s clear to me that the future of work will depend on the degree to which we can all collectively figure out how to harness and leverage generalist value.

Coming up soon…

I’ve got some more neat articles in the works, exploring business models for service providers, the future of fractional work, UX design for client service, and more.

Until then, I thank you from the bottom of my heart for joining me in reading this ???? Reach out to me directly if you want to chat about it!

Please comment on this post with a ‘spice’?emoji ????or perhaps a 'squiggle' ?? emoji to indicate that you read to the end.

Thanks! See you next time

?? & ??

Important note: This article, like all articles I publish, made no use of artificial intelligence whatsoever. All words, thoughts, observations and expression in this piece are 100% human-generated. I recognize the value and opportunity that AI technology represents for us (especially within the context of this piece!), but when it comes to these articles that I write here, the primary goal is to fuel my writing practice, and so I avoid any and all use of AI tools. Not sure if this even matters to anyone reading, but in today’s world where it’s pretty hard to know what a human produced and what a machine produced, I figured it was worth mentioning.