How Great Generalists become Specialists

At first glance, it is easy to assume that all specialists are different, and generalists are more or less the same. I think the opposite is more true.

Generalists vs. Specialists

Generalists meander between fields, collecting ideas from one field and applying them to another. They study broadly, seeing patterns, and looking for commonalities and differences in disparate pieces of the world. To do this they often sacrifice depth.

Specialists focus intense effort on a specific area or problem. They explore the extreme depths of their field, often up to the frontier of knowledge. To do this, they often sacrifice well-roundedness.

Generalist vs Specialist -This is Matt’s actually professional drawing job.

This is Matt’s actually professional drawing job.

Specialists are always going deeper and deeper in their direction, more and more precise with their area. This post from @MattMight gives a great visual explanation of how education progresses from general to specific:

The red spike in a specific direction represents increasing specialization through Bachelors, Masters, and Post-grad education.

I believe this graphic also works for increasing skill and domain specialization in private markets as well. Imagine an investor who spends her entire career in Currency Speculation markets and becomes increasingly skilled and experienced.

In visualizing the pattern of a generalist, the shape is a little more erratic. Spikes of all shapes shoot out in all directions — usually determined by topics of interest to the generalist, products of life experience, or just however ideas daisy-chain into each other.

Generalist vs Specialist: This one I drew… with 1,000 apologies.

This one I drew… with 1,000 apologies.

Because the generalists are likely to be charting their own path, and the specialist is more likely to be progressing down a known (or at least directionally similar) path — the generalist is actually more likely to stumble into a novel shape than a specialist who is carefully keeping their line straight.

If specialists are drops of water, generalists are like... unique snowflakes.

We can actually see how generalists become unique. Generalists slowly accumulate new bubbles and branches, until they develop a completely unique set of skills, knowledge and experience.

That unique shape means they are a kind of “key” — those skills and experiences have uniquely prepared them for unlocking… something.

"Your goal in life is to find out the people who need you the most, to find out the business that needs you the most, to find the project and the art that needs you the most. There is something out there just for you.” - Naval Ravikant

As generalists progress through time, they become unique.

By becoming unique, generalists become… specialists.

The challenge then is finding out what your unique generalism has prepared you for.


This specialism can be a surprise to the unique generalist, when they happen upon an opportunity that is the perfect puzzle for their skills, experiences, and knowledge.

Consider how often this plays out in stories. Indiana Jones is a unique generalist. James Bond is a unique generalist. Louise Banks, the heroine of Arrival, is a unique generalist.

Consider Barack Obama. He is a very unique generalist. On the way to becoming President, he became adept at: Community Organizing, Law, Philosophy, Public Speaking, Making Friends and Influencing People, Raising Money, Campaigning, and 500 other things that come with holding public office.

(I happen to be reading “Becoming” by Michelle Obama right now, so Barry is top-of-mind. It’s especially good in Audible — She won a Grammy for it!)

Speaking of Barrys -- another story is Nathan Barry of Convertkit. Even businesses can move from being generalists to specialists. 

In 2015, Convertkit decided to refocus on a narrow niche: creators. Previously, they had a ton of competitors and Convertkit had trouble gaining traction. They stayed focused on creators and resisted the distraction of other customers. 

Today, they’re still focused on creators and have “the best product, team, and customers” in their chosen niche. Becoming a specialist helped Convertkit outlast their competition.


The reverse can also be true — truly great specialists become generalists. As specialists reach the end of known practices in their field, they will increasingly look to pull in ideas from other fields. Everything is interconnected. Our career expert in currency speculation may need to learn more about the history of European trade disputes or post-war reconstruction efforts in order to continue to level-up in her specialization.


I think the generalist vs. specialist debate is overblown. I know very few people who clearly qualify as obviously one or the other.

For even the most dedicated specialists I know, by midlife they have specialized in enough different things to have created a beautiful, deep mosaic of interests that makes them a well-rounded, fascinating friend.

For even the most meandering generalists I know, they have wandered far enough into the esoteric to have very special types of knowledge, wisdom, or experience.

We choose problems to solve, and “who we are” emerges as we work to leverage our unique abilities against the problem we have chosen.

Holler @ me with your thoughts.