Generalists and Specialists

"Taylor Swift for generalists, Whitney Houston for specialists"

Choosing their career path between a generalist and specialist is a common dilemma that I think many people in their 20s share.

One big reason is the absolute time commitment required to become a specialist. In most fields, 20s are not yet old enough to have put in the time to mature their skills. Most of the "great" surgeons are over 50. Many of the "best" senior developers are in their 30s and 40s. People in their 20s have not yet spent enough time to hone their skills, and the specialist track seems tough and tedious like walking towards a North Star far far away.

On the other hand, the generalist path has the risk of insecurity and ambiguity. Especially in the startup scene, as described in the book <Blitzscaling>, the pace of change so fast that it is imperative to hire generalists who are ambidextrous and adaptive. However, having all-around abilities with no outstanding specialty makes you feel as if you are replaceable, and there are times when your various day to day tasks seem to lead nowhere. These people tend to experience career crises when they fall into the notion that they are a master of none, and that their career path is cluttered and irreversibly ruined.

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This is a dilemma that I experienced myself for quite some time, so I take these matters to heart.

I'm a jack of all trades — I can build, I can strategize, I can analyze data, I have product sense, and I can sell — all at a professional level. I've even studied medicine in college. There were times when I thought, "Where is this resume leading to?”.

When I was coding, I didn't aim to be the best software developer in the world, and when I was studying, I didn't aim to be the best doctor in the world. I practiced with the mindset of being good enough rather than aiming to be number one in the group. Because our society rewards competition, there were moments when I felt out of line, and that my reward function needs to be recalibrated. Deep down I believed I had the experience and skills as a general problem solver, but it was literally a very generic skill to consider as a differentiating specialty.

After much thought, I recently came up with a definite answer to this slippery balance, and here it is. To summarize, generalists can think of themselves as Taylor Swift, and specialists can think of themselves as Whitney Houston.

"Taylor Swift for generalists, Whitney Houston for specialists"

Taylor Swift does all the composing, lyrics, producing, and singing by herself. In terms of skillset, you need to be a jack-of-all-trades to pull this off. While she may not be the best in the world at any particular single skill, Taylor Swift is able to produce songs that catch the public's ear, which is why she is immensely successful as a singer-songwriter.

On the other hand, Whitney Houston is super specialized as a singer. She can't compose or produce a song, but she can do that one job: singing, exceptionally well. She's one of the best in the world, and that's why she's recognized and successful as a singer.

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Let’s come back to the world of business. Like Taylor Swift, in order for a generalist to be successful, he or she must create a product that sells (= “the entrepreneur track”). There are so many skillsets required to create a successful product — building, selling, recruiting, organizing, and executing — that specialists can't dare to pull off. It's about your intuition, your story, and your product. If you are a generalist who creates something totally new, that is when you become truly irreplaceable. Specialists speak with their skill, and generalists speak with their creation [1].

What follows like a corollary, is the yardstick for how good a generalist/specialist should be in each area.

A specialist's yardstick of skill is relative to their peers. You have to be better than everyone else to be treated well, and you have to train to be number one. In other words, you are rewarded with relative skill, not absolute skill.

Generalists, on the other hand, should have good enough skills to create a product that sells. In other words, they have an absolute yardstick, one that is dependent on the customer of their product. Taylor Swift doesn't need to be the best producer in the industry, she just needs to be good enough to create music that people want to listen to. [2][3]

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There's one more thing to keep in mind here. The process of "getting better" is inherently painful, a battle with yourself, and a process that requires time and grit.

In my life, it took blood, sweat, and tears to get good at certain skills. To get good at coding, to get good at basketball, to get good at studying medicine… the process took discipline and grit. This painful process as a rite of passage applies the same regardless if you are a generalist or a specialist. What's different is the extent of how far you have to hone your skills; whether it’s absolute (good enough for customers to buy) or relative (#1 expert in the business). There are no shortcuts that bypass the hard work and perseverance that goes into building your skills.

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I'll end this with a personal reflection. I'm a jack-of-all-trades. There were times when I thought, "Where is this resume leading to?”. But now I have a clearer view. I was born to be a generalist, and to succeed as a generalist, I will create a new product and sell it to the world. I'll accumulate the necessary skills to make a successful business, and once I'm good enough, I'll try again and again until I create that product-market fit. I will become Taylor Swift.

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Notes

[1] As you move up to the C level, you can't afford to keep contributing as an individual contributor, because the abstraction layer gets too high. Therefore taking on a high-level position in the company is another viable route for generalists to succeed. It's important to note that creating isn't always the only answer, and it's dangerous to think of generalists and specialists as binary, as it's a continuous spectrum where everyone is a mix of each.

[2] Even if you're a generalist, there are times when your skills aren't enough to build a product. That's when you need to convince others with your competence. In the early stages, when the product is before product-market fit, you need to sell yourself to recruit talents, and the better your skills are, the easier it is to convince others. In other words, another yardstick of skill for generalists is the degree to which you can convince others. Especially if you are a CEO with engineering backgrounds, you may need to recruit your engineers in this way, since engineers look up to greater engineers than themselves. (e.g., Guts and Griffith's first meeting in <Berserk>)

[3] There are also areas where specialized knowledge is required to build a business (e.g., deep tech). The difference here is the nuance of "build enough expertise to make a product and then stop" vs. "do not stop and take your expertise to the highest level". In deep tech, you should be in it for the long haul, as market opportunities and problems can only be seen once the founder has reached a certain level of sophistication, often labeled in the form of a Ph.D.