Newsletter 82: Specialists VS Generalists, T-shaped people and don't climb the wrong hill

We are taught from an early age to specialize. Our parents frequently remind us of the importance of picking a lucrative profession. Universities are designed to force a choice of specialization as soon as you graduate high school. But, most importantly, the labor market rewards specialists a fair bit more than generalists.

Think of the average job description. Most JDs are written to attract people with experience in a niche field. Job interviews are the same. The employer asks questions to understand the depth of your specialization rather than your ability to adapt and leverage different fields. As a result, we all experience pressure to figure out what we want to do at every major step of our lives.

Specializations like being a doctor or a lawyer are glorified because of the critical role they play in society. But there is little regard to how we feel about taking on such roles. Most people grow up feeling insecure and confused under all that pressure. I cannot blame them; it’s not easy to find out what you want to do so early. Such a decision will have a long-term impact on your ability to earn and support your loved ones.

Specializing early is what people call “conventional wisdom” or “timeless advice.” That stems from the Lindy effect, which proposes that the longevity of an activity is proportionate to its life expectancy. Meaning the longer something survives, the more confident we are that it will continue to exist.

Historically, specializing has been necessary. Our survival depended on specializing in agriculture, healthcare, governance, art, education, etc. But as the world is getting more and more complex, I am not sure if that’s still the case. Adhering to practices that have worked in the past is like outsourcing significant decisions in your life. Decisions that will impact your career trajectory, income, and potentially your happiness. This begs the question, do you want yesterday’s wisdom to guide your entire life?

Before I move forward, let me offer a disclaimer. I am not entirely against timeless advice. There are many examples of timeless advice that most likely is still true today. Starting a war is wrong. Drinking excessively causes health issues. Gambling brings the risk of ruin. History has shown us the consequences of such decisions. There is no need to go against all conventional wisdom and question it. Having said that, it is vital to be selective when making life-changing decisions.

From specialist to generalist

When I look at my own life, I made the mistake of trying to be a specialist way too early. I graduated primary school with the highest possible GPA in Bulgaria. As a result, I could enroll in any high school in Sofia. While my parents did give me the freedom to make my own choice, they advised me to pick a profiled high school.

Profiled high schools were a relic from the soviet union. Institutions designed to teach you what regular schools cover, plus the basics of a specific profession like chef or mechanic. Given how my family did not have a lot of money, picking a school that could get me a part-time job while studying was a no-brainer choice. So I found myself selecting a hospitality profiled school.

A few years into my studies, that bet paid back. I was working part-time at all major five-star resorts in the capital. My evenings and weekends were consumed by events where I worked as a waiter. The payment was decent, and I quickly outpaced my parents’ earnings. At the age of 17, I received my first leadership role while earning more than anyone in my entire family. The more I specialized, the more valuable I became. At that time, I could get a job at any restaurant or resort in Bulgaria. The compounding benefits of specialization started bearing fruits.

When I turned 18, I moved to Denmark to continue my studies—taking on another degree in Hospitality Management. That led to management training in a branch of Novotel located in Taiwan, where I was offered a full-time leadership position. So naturally, I started asking myself, is a career in hospitality what I want to do? It turned out, I was not sure, which led to returning to Denmark to continue my studies.

Once back in North Denmark, I attended a startup weekend event. That event opened my eyes to an entirely new world. Throughout a weekend, I got a taste of the tech sector, entrepreneurship, and a few different industries. My curiosity was satisfied like never before. The whole experience felt just right. Something inside me clicked.

Suddenly, I realized how little thought I put into selecting my specialization years back. As an outcome, I got good in a field that did not satisfy my curiosity. A profession that did not bring the growth and self-actualization I was subconsciously seeking.

On the other hand, the world of startups exposed me to many different roles like marketing, sales, fundraising, finance, legal, product, human resources, and everything in between. The more I dived into entrepreneurship, the more I learned about each field. While I was not becoming an expert in any of them, I learned just enough to be dangerous over time. That experience taught me how you do not need to be a world-leading expert in any field to succeed. All you need is a strong bias for action and basic knowledge to make quick decisions.

Generalists are underrated

My generalist’s journey has been nothing short of rewarding. It helped me explore various fields, industries, and even a few cultures. The broader my experience got, the more valuable I became. The pivot to startups and tech started paying back. Whereas specialists outperformed me in their field, I could see the big picture. The interconnectivity of how different teams operate became crystal clear in my eyes. It felt like a puzzle was being completed in front of my eyes. The broader context offered a perspective only a founder can have.

I have written in the past about the founder mentality and its importance. Thinking like a founder is an invaluable and highly rewarded skill. Yet, in my experience, it’s difficult to adopt such a mindset if you do not have a decent understanding of how unrelated teams work. To gain that understanding, you need to expose yourself to various problems and tasks. The more you execute, the better you understand a) your strengths b) how unrelated fields connect.

Some degrees attempt to give you a holistic overview of how a business works, but even then, it only scratches the surface. Nothing beats the experience of jumping on a new, utterly foreign problem, and doing your best to learn, experiment, and eventually solve it.

Here you go, my thoughts on why embracing a generalist mindset is a better bet for an asymmetric upside:

• Generalists love analogies. Analogical thinking helps you to take what’s new and make it familiar, or take the familiar and put it in a new light.

• Specialists rely on overlearned behavior. If the world was static, repeating similar best practices would always work. Unfortunately, that’s not the case. Technology is changing the world so fast that, more often than not, existing tools/strategies/practices may not be applicable any longer. We are often fooled by expertise. Generalists, on the other hand, are not afraid to test new novel approaches or borrow from different industries.

• It’s the combination of specialists and generalists that creates outsized returns. When IBM Super Computer beat Gary Kasparov in 1997, many people's first thought was that humans seemed to have lost to the machines.
  But in AI, there is something called Moravec’s paradox “machines, and humans frequently have opposite strengths and weaknesses.” So Kasparov wondered what would happen if a computer played alongside a human. A machine that can assess two hundred million possible moves a second alongside a human who could demonstrate big-picture strategic thinking. The outcome was that supercomputers and grandmasters lost to amateurs paired with computers.¹

• People who have diverse experiences are more likely to succeed. For example, research at MIT and the U.S. Census Bureau found that the fastest-growing startups are run by founders who are forty-five at launch. A potential correlation here could be the exposure to different fields in the course of one’s life.

• In some fields, specialization does make a difference, for example, poker players and surgeons. But in most fields, the game rules are often unclear or incomplete. The solution is not always apparent in such circumstances, and a generalist approach might be better.

• Having a generalist mindset comes with humility. Knowing that you are not an expert in any field helps you stay firm on the ground.

The intersection of generalists and specialists

There s a framework designed by Brian Balfour called T-shaped background, which demonstrates how you can make the best of both worlds.

T-shaped people are both generalists (highly skilled at a broad set of valuable things - the top of the T) and experts (among the best in their field within a narrow discipline - the vertical leg of the T).

To illustrate the T model in motion, Brian Balfour takes the example of a marketing generalist.

The top of the T is divided into three layers: Base (knowledge layer), Marketing (foundational), and Channel (expertise). Meaning on the very top, you have broad, somehow unrelated knowledge. But as you dive deeper, that breaks down into specializations and tactical implementation.

Shaping yourself like a "T" would guarantee you a great culture fit in most fast-growing companies. Presenting yourself as a generalist decreases the probability of securing a role in a fast-growing business. But having deeper expertise in one or two areas will give you the leverage to take on any problem.

Source: Watch Brian Balfour (Formerly VP Growth @ HubSpot) Talk About How To Become A Customer Acquisition Expert

In my case, the vertical leg of the T is being shaped around content marketing. Hence why I write so much. I want to polish that skill, and only repetition, discipline, and feedback can help me improve. The combination of concise writing and knowing a bit about any area of running a business has proven to be invaluable over the years.

Climbing the wrong hill

An important distinction between specialist and generalist career paths is how different the road ahead looks. As a specialist, it is pretty clear what you have to do to thrive in your field. Mastering your niche will inevitably lead to success. On the other hand, that’s not the case as a generalist. Generalists often need to zig or zag or even walk backward before going forward. As a generalist, the path is not clear, which naturally scares many people.

Sometime back, Chris Dixon wrote an essay titled climbing the wrong hill where he describes a classic problem in computer science called hill climbing.

The hill-climbing exercise makes you imagine that you are dropped at a random spot on hilly terrain. Because it’s unfamiliar terrain, you can only see a few feet in each direction, but your objective is the get to the highest hill.

At first glance, people tend to take a step in the direction that takes them higher. But what if you happen to start at the lower hill thus end up climbing the wrong mountain?

Perhaps a better approach is to add some randomness into your trek. What if you start with a lot of randomnesses and then reduce it over time? That would give you a better chance of ending up near the bigger hill before you start your focused, non-random trek. The more you explore, the higher the probability of discovering the highest hill.

Going back to the specialist vs. generalist dilemma. The specialist has not explored the terrain very well. So he may believe how he is climbing the highest hill, but is that true? Perhaps, he will end up seeing the higher hill from where he stands.

“But the lure of the current hill is strong. There is a natural human tendency to make the next step an upward one. He ends up falling for a common trap highlighted by behavioral economists: people tend to systematically overvalue near term over long term rewards.  This effect seems to be even stronger in more ambitious people. Their ambition seems to make it hard for them to forgo the nearby upward step.”

Chris Dixon, partner at a16z

My advice is to avoid climbing the wrong hill. Instead, add some randomness to your walk. Over time you will start uncovering different things about your personality. Especially, what you are good at. At that point, begin decreasing the randomness. Once you find the highest hill, go for it. Do not waste time on the current one, no matter how much better the next step might seem to be. The long-term rewards of having a generalist journey (perspective, speed of decision making, growth, and learning) outweigh what the shorter hill offers (pay, title, and acceptance by society). So keep on climbing but add randomness to your walk.

1. “Range: Why Generalists Triumph in a Specialized World” by David Epstein