11 Aug 2023

Rethinking the Dichotomy: Generalist vs Specialist in 2023

We dive into: The 4 Archetypes of a Generalist, a framework for squiggly career progression, I'll then spin these into real-world examples of what a *delightful* generalist career flow could look like

And then... a pinch of spice 🌶️ I'll be busting the myth that generalists can't reach mastery

💡 Rethinking the Dichotomy: Generalists vs. Specialists in 2023

We’ve all heard it, and at one point, I’d even said if I heard it one more time I was going to scream 🙃 The age-old battle: Generalists VS Specialists.

I know, I know. It’s tired. And so are we from hearing about it. But alas, I’m here to offer a fresh perspective.

What if it isn’t about who wins the "versus" showdown?

What if that’s the wrong question to be asking in the first place?

What if we made a tiny, but critical change to the lens at which we look at this?

What if we shift from VS to PLUS?

Let me start by stating the obvious — the world, and humans, are nuanced.

We’re complicated, complex beings hurtling through space at 1.3 million miles per hour.

With any nuance, there are pros & cons.

Let’s lay them out.  

The Case For A Generalist

Generalist Pros:

  1. Big-Picture Vision: Generalists are like those panoramic cameras, capturing the whole scene. They excel at seeing connections that specialists might miss, making them the secret sauce for innovative problem-solving.

  2. Adaptive Dexterity: Adaptability is a superpower. Generalists can switch hats quicker than a chameleon changes colours, which is gold in today's ever-shifting (and very uncertain) job market.

  3. Interdisciplinary Magic: Ever seen someone juggling conversations about operational excellence, the sci-fi book they’re writing, and the community they’re building? That's a generalist in action, forming connections across different fields effortlessly. We see it all the time in the GW Community — the diversity of topics & knowledge keeps us all on our toes.

Generalist Cons:

  1. Missing Mastery: While they're the Swiss Army knives of skills, generalists might not boast the same level of mastery, or the depth fo domain experience, as specialists.

  2. Identity Crisis: In some circles, being a generalist can earn you a sceptical side-eye. Generalists report feeling misunderstood and overlooked. Specialists often own the spotlight as the go-to experts in their niches. Whereas generalists have to fight that little harder to gain the same credibility.

  3. Career Path Maze: While specialists have a pretty linear path to follow, generalists might feel like they're navigating a labyrinth with no map. It's exciting, sure, but it can also be a bit unnerving. This is where having a community of people to support you when you’re in the depths of the labyrinth is so crucial.

The Case For A Specialist


  1. Niche Ninjas: Specialists dive deep into their chosen field, becoming true authorities. They're the virtuosos who can make the most complex problems seem like child's play. They know a field or a domain inside and out.

  2. Trailblazers in Their Realm: Specialists can climb the ladder of success within their chosen field. They become recognized authorities, which can lead to speaking engagements, publications, and more thought leadership opportunities.

  3. Precise Problem Solvers: When it comes to tackling complex issues within their domain, specialists are like surgeons with a scalpel. They know exactly where to make that incision.


  1. Tunnel Vision Trouble: While they're masters of their craft, specialists might miss out on the broader strokes of what's happening in the world. Picture them as a chess player focused on just one corner of the board.

  2. Technological Disruption: In fields that are highly susceptible to technological disruption, specialists can find their skills outdated if they don't stay updated with broader industry trends.

  3. Specialization Risk: Going all-in on one speciality can also be a risky bet. If the demand for that expertise wanes, specialists might find themselves on shaky ground.

⚖️ The Future of Careers: Generalists PLUS Specialists

As we step into the uncharted territory of 2023 and beyond, it's not a battle between generalists and specialists. It's about embracing the power of ‘plus’.

It’s about collaboration. Seeing people for their unique perspectives and differences, and leveraging that.

It’s about diversity of thought.

It’s less about squeezing people into a box that just isn’t made for them, and instead asking ‘how can we better facilitate people to work in their own zone of genius?’

The Winning Formula…..🧪 🧪 🧪 🧪 

🤹 Balancing Depth and Breadth

At its simplest, it’s the best of both worlds:

  1. Leveraging Depth and Breadth: This approach enables individuals to excel in their chosen area while drawing upon interdisciplinary skills to innovate and adapt.

  2. Navigating Uncertainty: In an unpredictable job market, the "plus" model provides a safety net. If a specialist's niche becomes less relevant, their broad skills can open doors in other domains.

🔖 Case Studies: The "Plus" Pioneers

Dharmesh Shah

Meet Dharmesh Shah, the brains behind HubSpot. He's not just a tech wizard; he's got marketing savvy up his sleeve too. Shah's blend of skills didn't just build a product—it reinvented how we market tech.

Tim Ferriss

Ever heard of the "4-Hour" phenomenon? That's Tim Ferriss, the master of productivity. But guess what? He ventured into podcasting, investing, and advising, proving that being a "Specialist PLUS Generalist" is where the real game is. (ps: here he speaks about how generalists are making a comeback).

Wes Kao

An accomplished entrepreneur, educator, and marketing strategist who has left her mark on wide-ranging industries. As the co-founder of Maven, Wes is dedicated to equipping professionals with a versatile skill set that prepares them for success in an ever-evolving professional world.

🚗 The Road Ahead: Amplifying The ‘Plus;’

The only certainty about the world at the moment, is that it’s uncertain. In 2023 and beyond, the "Generalist PLUS Specialist" approach is a strategic, and in my opinion, well overdue, evolution of the traditional debate. Embracing both deep expertise and versatile skills is a formula for resilience & innovation in an unpredictable world.

I can’t help but wonder.. What is possible when we combine the strengths of generalists plys specialists?

As we redefine the conversation from "versus" to "plus," we pave the way for a new generation of professionals who can not only excel but thrive in the face of complexity and change. So, whether you're leaning towards specialization or are drawn to a wider range of skills, remember that in today's world, the magic lies in the "plus."

🕊🐸 From another view…. Are you a bird or a frog?

Eminent physicist and mathematician Freeman Dyson said: "we need both focused frogs and visionary birds".

Birds fly high in the air and survey broad vistas out to the far horizon. They delight in concepts that unify our thinking & bring together diverse problems from different parts of the landscape.

Frogs live in the mud below & see only the flowers that grow nearby. They delight in the details of particular objects, & they solve one problem at a time.

As a mathematician, Dyson labelled himself as a frog but contended:

"It's stupid to claim that birds are better than frogs because they can see farther, or that frogs are better than birds because they see deeper".

The world is both broad and deep. We need birds and frogs working together to explore it. Even in the most hyperspecialized specialities, it's possible to cultivate land where both birds and frogs can thrive.

One of the most beautiful analogies I've heard yet, taken from David Epstein's incredible book: Range. How generalists triumph in a specialized world.

For me, the question isn't 'Which is better, a generalist or a specialist?'

The question is 'How do we create environments where we can work to our strengths, however they might shine, together?'

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Our content is brought free to you, courtesy of the Generalist World community memberships.