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Generalist vs Specialist: How-to Approach Life

By Marco Gutierrez —

Back in elementary school, I was told it wasn't so difficult for someone to have multiple professions in ancient times. A person could perhaps be both a philosopher and an alchemist. Apparently, since the collective human knowledge wasn't so deep, it would take very little time to become an expert in something. This makes sense. But today's landscape has greatly changed. Specialization is the norm, what everyone wants. Most people seem to consider a college degree (or a Ph.D.) as the culmination of specialization, the ultimate goal. Is this modern de facto approach really the best way to go about our lives?

In general, it is most reasonable that being successful will make you happier, though it may shake your worldview if you realize you didn't actually want what you thought you wanted. And successful people seem to be specialists (more often than not). If you're aiming for raw success in life, should you aim to be a generalist or a specialist? Would there be a tradeoff between success and happiness with either choice?

Think about it. Wouldn't you agree Leonardo Davinci's many endeavors helped him across the board? Wasn't he a better painter because he was also an engineer? A better sculptor because he designed machines? A better thinker because would write his notes backwards? Remember: the first Macintosh had the most beautiful typography at the time because Steve Jobs took a calligraphy class when he decided to drop out of college. In great measure, because Steve Jobs went wide (and not deep) is that you are reading this article with this font.

Observations like this make me wonder: Why do most people wish to become specialists in a given field, technology, and/or company? It isn't obvious to me that this is best. Today, I'll argue there are times in life when we should be aiming to try new things. But we should eventually settle down and specialize. And doing this leads to better long-term success and happiness.

As a reference mental model, collective human knowledge can be seen as a series of mining caves. It used to be that people could reach the end of each cave very quickly because we hadn't dug too deep yet. But nowadays the tunnels are so deep that we devote close to a quarter of our life expectancy to just get to the point where we can dig a bit more.

A simple mental model for the collective human knowledge

Making a name as a generalist (someone who has traveled many tunnels, though partially) has never been more difficult. People just won't be too impressed even if I can both make my own toothpaste and also compose a piece of music. That would've been unbelievably impressive hundreds of years in the past. I can't bring to mind the name of a person who is famous for being good at many things. I can only recall people who are very good (if not the best) at one thing. But being famous isn't a good indicator of a happy fulfilled life. If I could convince you that you'd be happier and more successful by being a generalist, wouldn't you want to be one? The problem is it's hard to notice the success of unpopular people.

At the same time, it has never been easier to be a generalist. Provided you are one of the lucky people who has access to the internet, you can learn most human endeavors: Music, Design, Engineering, Science, Arts, Politics, Accounting, etc. Although I can't be considered a chef just for baking myself a cake, such a skill can't be disregarded. Of course, there's a degree to which a person is a generalist and a specialist. So how should you navigate this situation that life is giving you?

American author of books on strategy, power, and seduction, Robert Greene, gives the following advice on how to spend our youth:

The two-track mind... is the source of power.... Adventure and developing skills, those two together, that kind of attitude towards life in your 20s, will be key.

Paraphrasing Robert's main lesson here, you should aim broadly at what you want to become (Music, Writing, Business, Tech, etc.).

  • Don't just do one thing: don't just study law school and do that for the rest of your life. That'll make you miserable.
  • Don't spread out so much: you have to settle down for something eventually (ideally by your 30s but don't stress too much about it). Otherwise, your life will be unfulfilled.
  • Try to be good at a couple of things, aim for learning while adventuring and your life's purpose will come to you in due time.

I couldn't agree more with Robert here. And in great measure, his advice is what made me take the jump to leave my job at Google in pursuit of adventure, creative work, and personal projects (like this blog). But this advice only talks about being a generalist at a young age. We should eventually specialize later in life, shouldn't we? Let's contest that for a moment.

It's been my experience that humans are natural generalists. I have never really seen someone be one-dimensional in their life other than by choice. But this contrasts greatly with self-made millionaire Sam Oven's video on productivity:

I agree with Sam Oven's argument that the way to be more productive is to do less, not more. And it would seem that doing this is also the way to make more money. But what I don't think is that this is the way to fulfillment. If all you want is money (and I think you should be very careful to wish only for that), the best way to go about it seems to be the BEST at ONE thing and don't do it for free. The best way to become the best at one thing seems to be to stop doing most other things, even preparing your own food.

Just being a specialist is also risky. There's already talk about how AI may replace overall development jobs as a whole. It doesn't seem smart to put all of our eggs in one basket.

I struggled for a long time on this topic until I came across the following video. This really solved the puzzle for me. It aligned with all my previous observations and completed the big picture of how to go about life:

The video's title doesn't seem related to the topic of today. But interestingly, I now consider "falling behind" like a forced opportunity to become a generalist for a while. What we should remember from the video is the following:

Note: I'll be quoting directly from the video but removing or rephrasing certain parts to give a better reading experience.

  • The 10,000-hour rule: "To become great in anything takes ~10,000 hours of focused practice, so you better get started as early as possible". Tiger Woods exemplifies this greatly. His father gave him a putter at 7 months old. At 10 months, he was imitating his father's swing. At 2, you could see him on national TV. At 21, he's the greatest golfer in the world.
  • Notwithstanding the 10,000-hour rule, future elites actually spend less time early on in deliberate practice in their eventual sport. They tend to have a sampling period, where they try a variety of physical activities, gain broad general skills, learn about their interests and abilities, and delay specializing until later than peers, who plateau at lower levels.
Deliberate practice chart for elite and near-elite athletes
  • Exceptional musicians don't start spending more time in the practice than the average musicians until their third instrument. They too tended to have a sampling period. Even musicians we think of as famously precocious like yo-yo ma. He had a sampling period. He just went through it more rapidly than most musicians do.
Deliberate practice chart for exceptional and average musicians
  • Who wins the trade-off: the early or the late specializers? The early specializers jump out to an income lead because they have more domain-specific skills. The late specializers get to try more different things and when they do pick they have better fit, so their growth rates are faster. By six years out they erased that income gap. Meanwhile, the early specializers start quitting their career tracks in much higher numbers, essentially because they were made to choose so early that they more often made poor choices. The late specializers lose in the short term and win in the long run.
Income and persistence tradeoffs between early and late specializers
  • Hyperspecialization can backfire badly. According to research, people who get career-focused education are more likely to be hired right out of training and more likely to make more money right away. But so much less adaptable in a changing work world that they spend so much less time in the workforce overall. They win in the short term and lose in the long run.
  • Golf is a uniquely horrible model of almost everything that humans want to learn. Golf is what psychologist Robin Hogarth called a kind learning environment. Kind learning environments have next steps and goals that are clear, and rules that are clear and never change. When you do something to get feedback that is quick and accurate. Work next year will look like work last year. On the other end of the spectrum are wicked learning environments, where the next steps and goals may not be clear. Rules may change. You may or may not get feedback when you do something. It may be delayed. It may be inaccurate. And work next year may not look like work last year. So which one of these sounds like the world we're increasingly living in?
  • If hyperspecialization isn't always the trick in a wicked world, what is? Sometimes it looks like meandering or zigzagging or keeping a broader view. It can look like getting behind.
  • The most impactful patents are not authored by individuals who drill deeper into one area of technology (as classified by the US Patent Office) but rather by teams that include individuals who have worked across a large number of different technology classes and often merged things from different domains. Check out the story on the video about how the Gameboy came to be. It's jaw-dropping. Its author's creative philosophy translated to "lateral thinking with withered technology": taking well-known technology and using it in new ways.
  • This breadth advantage holds in more subjective realms as well in a fascinating study of what leads some comic book creators to be more likely to make blockbuster comics. A pair of researchers found that it was neither the number of years of experience in the field, nor the resources of the publisher, nor the number of previous comics made. It was the number of different genres that a creator had worked across. And interestingly, a broad individual could not be entirely replaced by a team of specialists. We probably don't make as many of those people as we could because early on they just look like they're behind and we don't tend to incentivize anything that doesn't look like a head start or specialization.

David Epstein ends the video with the following, which I think hits the nail on the head concerning our topic of today:

I think there are as many ways to succeed as there are people. But I think we tend only to incentivize and encourage the tiger path, when increasingly in a wicked world we need people who travel the roger path as well. Or as the eminent physicist, mathematician and wonderful writer Freeman Dyson put it... "For a healthy ecosystem, we need both birds and frogs. Frogs are down in the mud, seeing all the granular details. The birds are soaring up above, not seeing those details but integrating the knowledge of the frogs. And we need both. The problem is that we're telling everyone to become frogs.". And I think in a wicked world that's increasingly short-sighted.

So there you go. Given the referenced materials and observations of today, it seems most reasonable that there are human endeavors that benefit greatly from the 10,000-hour rule (kind environments). But life seems to be more filled with wicked environments. And for those, it is best not to choose quickly and get a head start. Instead, we should meander at the beginning (as if we were "falling behind"). And things will eventually work out for the best and better in the long run.

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