Are You Better Off as a Specialist or a Generalist?
March 24, 2016

It happens all the time.

We are bombarded with advice – fashionable, trendy advice.

“Fat is the devil!” (1990s)

“Buy as much house as you can afford!” (Early 2000s)

Everybody around us has been seeing the results. Our parents and the media give a stamp of approval. It all makes so much sense to jump aboard… until one day… it doesn’t.

Next thing you know, the recitations have changed.

“CARBS! Carbs be gone! Stick with fat, stick with protein! TO HELL WITH CARBS!” (2010s)

“A mortgage is the man’s way of tying you down. When you buy a home, you become tied to a job, and you’ll have lost the battle for freedom in your life.” (2010s)

I’m not saying that new advice isn’t valid or helpful – it’s just contextual. Principles may be enduring, but tactics are circumstantial.

When it comes to our careers, you don’t have to look far to find the same feverish armchair quarterbacking.

“A college degree is essential to finding a high paying job.”

“Never leave a job that you’ve been in for fewer than two years.”

You also wouldn’t have to think hard about circumstances that contradict these nuggets of advice playing in the echo chamber. Richard Branson didn’t need a college degree, nor did Michael Dell.

And what if you someone offered you a $50,000 raise to walk away from the job that you started two weeks before? Would that be out of the question?

Hell no.

And hell no to answering contingent questions with black and white answers. We’re better than that.

One career question on many people’s minds is, “Should I specialize or work on becoming well-rounded to succeed?”

As per usual, there are two camps of people taking sides on the issue.

Team Specialist

This crew brings a number of good points to the table.

For one, they’ll start by asking, “has the world become more complex?”

Of course it has.

And in all of that complexity, lies opportunity.

We all know the person in the office that is a rock star. They might be a master of the politics, but at the end of the day, they know how to get things done. They have confidence, but a lot of that confidence comes from knowing their job cold. To put it frankly, they know things that nobody else around does – and that translates to power, prestige, and bargaining power.

I think we’ve all wanted to be this person at some point, watching with a level of admiration… perhaps even envy.

The only guy on the basketball court who can dunk, and the only guy in the group who can automate his work by writing a script have a distinct advantage. Specialization is a way for people to separate themselves from the crowd, get noticed, and accelerate their career.

Read Adam Smith, and you’ll get the feeling that specializing is something beautiful – that it marks the blooming of a capitalist system.


Obligatory Adam Smith pin manufacturing excerpt

To take an example, therefore, from a very trifling manufacture, but one in which the division of labour has been very often taken notice of, the trade of a pin-maker: a workman not educated to this business (which the division of labour has rendered a distinct trade, nor acquainted with the use of the machinery employed in it (to the invention of which the same division of labour has probably given occasion), could scarce, perhaps, with his utmost industry, make one pin in a day, and certainly could not make twenty. But in the way in which this business is now carried on, not only the whole work is a peculiar trade, but it is divided into a number of branches, of which the greater part are likewise peculiar trades. One man draws out the wire; another straights it; a third cuts it; a fourth points it; a fifth grinds it at the top for receiving the head; to make the head requires two or three distinct operations; to put it on is a peculiar business; to whiten the pins is another; it is even a trade by itself to put them into the paper; and the important business of making a pin is, in this manner, divided into about eighteen distinct operations, which, in some manufactories, are all performed by distinct hands, though in others the same man will sometimes perform two or three of them. I have seen a small manufactory of this kind, where ten men only were employed, and where some of them consequently performed two or three distinct operations. But though they were very poor, and therefore but indifferently accommodated with the necessary machinery, they could, when they exerted themselves, make among them about twelve pounds of pins in a day. There are in a pound upwards of four thousand pins of a middling size. Those ten persons, therefore, could make among them upwards of forty-eight thousand pins in a day. Each person, therefore, making a tenth part of forty-eight thousand pins, might be considered as making four thousand eight hundred pins in a day. But if they had all wrought separately and independently, and without any of them having been educated to this peculiar business, they certainly could not each of them have made twenty, perhaps not one pin in a day; that is, certainly, not the two hundred and fortieth, perhaps not the four thousand eight hundredth, part of what they are at present capable of performing, in consequence of a proper division and combination of their different operations.


The specialization crew will also ask, “does possessing a rare skill increase your job security?”

Of course it does.

Does it lead to better pay?


Does it make you a hot commodity?


Look at some of the world’s top performers – LeBron James is a good example.

How high is the demand for LeBron James?

Nosebleed high.

What is the supply of LeBron James (based on performance)?

Just about one unit of LeBron James.

Therefore, he can command the highest of salaries, the best endorsement deals, fame, fortune, you name it.

The same goes for elite actors, authors, lawyers, bankers. Mastering a special skill pays off handsomely when you are among the best.

That all sounds great, so what’s the other side of the argument?

Team Generalist

We can all point to a highly successful person in the public eye who claims they aren’t the smartest in the world.

Take Mark Cuban for instance, a billionaire businessman, reality TV star, and owner of the Dallas Mavericks.

Mark Cuban has great business instincts, and despite his larger than life personality, he shows a great deal of humbleness.

Mark Cuban? Humble? 

Yeah, sounds weird.

However, at every step of his career, you find cases where Mark rolled up his sleeves and did the work himself. More importantly, when he could afford to get out of the way, he stepped aside in favor of someone better equipped for the task.

If you read his account of starting Micro-Solutions in his mid twenties, you get a taste for all of the hats that he wore early on. He was writing his own code, out there making sales, running the company. As Cuban continued to succeed, he moved past a point that many entrepreneurs get stuck at – removing himself from the minutiae.

I picked Mark Cuban as an example because his story demonstrates the broad skill set of great managers and entrepreneurs. He succeeded as both.

So what is the benefit of broadening your focus?

Generalizing allows you to step back and see the larger picture. You become focused on the larger mission and begin to move pieces around on the board. Even LeBron James is a piece on the board. He is a well paid professional, but not an NBA owner.

LeBron has made just about $100 million since 2012 as a player.

Compare that to Dan Gilbert, owner of the Cleveland Cavaliers, who has earned $2 billion since 2012.

Franchise owners typically make more than even the best players out there, unless it’s a bad year.

What’s more is that Dan Gilbert or Mark Cuban would never have been able to reach such heights if they spent their time trying to master one thing.

You might make $1 million dollar salary as a specialist, but probably not even close. As a generalist, you at least have a shot at $1 billion.

The focus is different between both paths. The world needs chiefs, but it also needs Indians with the know how.

Successful generalists tend to build systems, only learning what they need to along the way. Specialists try to fit into a system and maximize their wages. One is begging to be replaced, while the other fights off replacement tooth and nail.

There is a saying that the jack of all trades is a master of none.

This implies that too wide a focus leads to poor results.

I’d agree, anyone trying to master 50 skills at once will conquer none of them. However, generalists are in the business of hiring talent for a larger vision. They are focused, but on a meta skill rather than a finite subject like tax accounting.

The Verdict

With all that said, where does it leave us? Should you spend your time mastering a skill or taking a wider approach?

As with most broad questions, you get a broad answer. It depends.

The first consideration is your taste for risk.

Are you looking for a cushy job, something that will pay all of your bills? Do you have a narrow passion that takes precedence over world domination?

Some people just like to code, or to write. It makes them happy, and they don’t need to engage in the stresses of building an empire.

With all of the fanfare surrounding passive income, tech startups, and Elon Musk fetishism, it can feel like wanting a normal job with a linear career path is some sort of sin.

I think this is a distortion resulting from the relentless promotion of personal development bloggers – you can do very well and be very happy in a narrowly defined specialty role.

The short term risk of specialization is low, but that risk mounts over time.

One of the main reasons we are told to go to college is to obtain knowledge and a degree that sets us apart from the crowd.

Why is manual labor some of the hardest work in our society, yet among the lowest paying work?

Supply and demand.

There are plenty of people in good enough health to lift, move, and clean. There are no barriers to entry.

Compare this to an actuary. It takes time to learn the math and statistics necessary to pass actuarial exams.

Not many people are willing to put the time in, or have the aptitude to learn it quickly. Therefore, fewer people are equipped to be actuaries than laborers with respect to demand for these roles. It’s no wonder that actuaries make more than most construction workers.

Specializing, either through training, certification, or reputation makes you more marketable, and less expendable…. but not forever.

When’s the last time you went to your local blacksmith? Never? That’s funny.

What about your stock broker? Oh, you use eTrade online?

The thing about specialization is that we live in a fast moving world. What you choose to devote years to may become irrelevant in a very short period of time.

I think of lawyers and cab drivers.

At one point lawyers with excellent knowledge of case precedent and law were highly valuable. People who committed an esoteric area of the law were compensated extremely well. They were either sought after by clients, or they served as consultants for other lawyers who landed a case.

Specialists still exist in the law profession, and many are still paid well. However, the advent of the internet has taken a bite out of many lawyers’ competitive advantage – a mind full of cases and research.

Today, a lawyer can access case rulings and court precedents by visiting Google or using a tool like Lexus Nexus. Memorized facts don’t cost as much anymore, because so much of humanity’s collective history is uploaded to the internet.

Some lawyers spent decades building a nest egg of knowledge that is now widely available.

The game has changed, and now people who can process the information best are most valuable. This evolution will continue, but the average worker’s secret stash of information is harder to hold onto than ever.

I learned that cab drivers encountered a similar change. Drivers with deep knowledge of an area and great navigation skills were sought after for clients. They could build a very valuable book over their careers.

However, navigation and local knowledge have been commoditized by navigation systems and the web. Cab drivers now face a commodity wage, which is being driven down further by ride sharing services like Uber.

As a specialist, you’ll probably have to retool every few years to stay competitive. The world is moving faster and there are fewer free lunches.

To pigeonhole yourself leaves you without diversification, and I have seen people of this mold who have imperiled their livelihood by staying still. Yesterday’s go-to-guy can become obsolete by the morning. Make sure you monitor the situation.

Is being a generalist any better?

In terms of flexibility, yes. You can remain more nimble in the face of change.

For instance, learning algebra in high school and calculus in college give you the foundation to solve problems in all sorts of disciplines, like engineering, medicine, and finance. However, it takes a while to get to the point where you are taking a graduate health economics course.

And as you go down the rabbit hole further your studies are less concretely applicable across disciplines. That graduate health economics course won’t make you a much better electrical engineer.

However, learning something fundamental like calculus could take you in a number of directions.

If you take the path of a generalist, then you can’t just be someone who sucks at a lot of things. 

This is a risk in it’s own right: being spread so thin that you are equally bad across disciplines.

A great generalist is somebody who has assessed the situation, learns enough to be dangerous in a multitude of relevant subjects, and can have a conversation with the specialists they’ve brought in to do the heavy lifting.

If you want to rise quickly, or own your own enterprise, you’ll probably have to broaden your appeal to gain credibility and to troubleshoot the diverse problems faced in business.

My Takeaway

Most people aren’t born with the keys to the kingdom.

We aren’t all heirs to the family company, or part of a country club network.

That said, you’ll probably have to start from the bottom.

That means earning an income, saving, and building relationships before setting off on your own.

The best way to get ahead early is to get a reputation for something.

Phase 1: Specialize 

The quickest way to get a good wage early is to become damn good at something. From an options standpoint, it’s much better to be great at something than it is to be mediocre in a lot of things.

This is counter intuitive.

Therefore, even great generalists like top CEOs and investors probably started out great at something.

Look at all of the actors and performers out there who will never get a large TV deal. Then look at someone like Michael Strahan, who bypassed all of these people for a slot in morning television with no background in the field.

He was great at football, became a household name from it, and had the option to go into television. Recognition can compensate for lack of training.

The key for somebody like a Lloyd Blankfein (a rock star commodities trader turned CEO of JP Morgan) is that they moved on before getting pigeon holed. Staying a specialist for too long can limit your options, but there’s a period where great specialists can choose from a number of options.

Phase 2: Generalize

Once you’ve acquired a reputation of competence, and have acquired the right financial and social capital to advance, you’ll be well equipped to step back and begin tackling a wider set of problems.

Executives and business owners know not to get too involved in the nitty gritty details. They need the right people under them to take care of specific problems so they can guide the entire system.

You wouldn’t want your ship’s captain to be washing the life boats while at sea. The mates are on board so the captain can avoid sinking the ship.

Wrapping Up

As with all of the conflicting wisdom out there, both sides are a little bit right and a little bit wrong in this argument.

Specializing can help you get ahead, but barriers to entry are eroding quicker than ever with the rapid advance of technology. Meta skills have more staying power than subject matter expertise.

At some point even the best specialists hit a wall. If they want to move up further, it usually requires tackling broader problems, are at least a larger set of problems.

If and when somebody is ready to take that step, they’ll have to start thinking as a generalist, who can understand and deploy resources to the many hazards encountered in business.

Both paths can give you a nice life, but you’re going to have to work hard and think on your feet either way.

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