Authors(s): David Epstein
Published: 2019

Overall Thoughts & Roadmap

I've been warned multiple times against dabbling in too many things - "you don't want to become a jack of all trades, master of none", the warning goes. I think these warnings are a product of the common belief that generalists (people who know a little about many topics) tend to be less successful than specialists (people who know a lot about a few things).

In this book, David Epstein argues and provides evidence that being a jack of all trades is not only okay, it can actually be an advantage!

This book summary is split up into the following sections:

(1) The benefits of being a generalist

(2) Advice on finding your purpose/calling

(3) Advice on being innovative

(4) Advice on learning

Problems with Specializing; Benefits of Generalizing

Main argument of this book

  • Common wisdom: To excel and be competitive, you need to specialize in one specific field. This means starting early in one field, sticking to it, and not giving up.
  • Epstein's argument against common wisdom: there are benefits to being a generalist. Most importantly, being a generalist allows you to bring together disparate ideas to come up with novel and creative solutions.

Problems with specializing

Kind vs. Unkind learning environments

  • Kind learning environments = environments where patterns repeat over, feedback is accurate and quick. (E.g. golf, chess)
  • Unkind learning environments = environments where the rules of the game are unclear or incomplete, patterns may not be repeated, feedback is delayed or inaccurate.  (E.g. teaching, writing, some service sector jobs)
  • In kind learning environments, experience may help you become better. In unkind learning environments, experience may reinforce wrong lessons.
  • Specialization only works in "kind" learning environments. It does not work in "unkind" learning environments.
  • The modern world increasingly requires people to work in unkind environments. Jobs in kind environments can be automated by computers.

Tunnel vision 

  • Specializing too much might lead you to dig deeper into your own field when solutions to problems in your field might be found in adjacent fields.

Benefits of Generalizing

The key skill to learn in the modern information economy is how to apply principles/methods you've learned from one field to problems/questions in another field (e.g. applying statistical methods to answer a problem in the humanities). One is only able to do this if you have knowledge in both fields and can break down barriers across fields of inquiry.

"The challenge we all face is how to maintain the benefits of breadth, diverse experience, interdisciplinary thinking, and delayed concentration in a world that increasingly incentivizes, even demands, hyperspecialization."

By exposing yourself to different fields, you are more likely to get better at recognizing similarities across domains that seem not to be connected. This is the key to innovating (more on this below).

"Deep analogical thinking is the practice of recognizing conceptual similarities in multiple domains or scenarios that may seem to have little in common on the surface."

Advice on Finding your "Purpose" 

Flirt with your possible selves

Keep sampling and experimenting in order to find things and people that match you well. This provides support for my belief in the benefits of failing like a scientist!

"Learning stuff is less important than learning about oneself. Exploration is not just a whimsical luxury of education; it is a central benefit."

There isn't one you, there are many you-s. Get to know each one of them!

"Rather than expecting an ironclad a priori answer to “Who do I really want to become?,” ... it is better to be a scientist of yourself, asking smaller questions that can actually be tested—“Which among my various possible selves should I start to explore now? How can I do that?” Be a flirt with your possible selves."

Know when to quit and when to persevere

  • There's a tension between escaping the sunk cost fallacy (wisdom here says: don't stick to an activity just because you've invested time/money in it) and the virtue of perseverance (wisdom here says: you should stick to things and persevere).
  • Epstein argues that knowing when to quit is a big strategic advantage. This is because finding something that matches you well (has a "high match quality") is more difficult than persevering in something that doesn't match you well.
  • The key is to know the difference between whether you're quitting because you can't be bothered to persevere or you're quitting because there's a better match available.
  • Be systematic and develop a decision system for when to quit. Before undertaking an endeavor, you should write down the conditions under which you would quit and give reasons for those conditions! 

Don't make long-term goals

It's hard to predict what our future selves will value.

"Our work preferences and our life preferences do not stay the same, because we do not stay the same."

Advice on Being Innovative

Use analogical thinking

  • Bottom line here is that to spur creativity, you want to find stimuli that are as distant as possible from the field you want to innovate in and then let ideas from the two fields collide.
  • Learn how to find various types of relations between things that seem to be unconnected. People are particularly bad at finding causal relationships between two things that have not been grouped together.

If you are an outsider, take advantage of that position rather than be ashamed of it

Being an outsider is a good thing some times.

"Knowledge is a double-edged sword. It allows you to do some things, but it also makes you blind to other things that you could do."

Combine lateral thinking with withered technology

  • Lateral thinking = drawing together disparate concepts or domains that can give old ideas new uses.
  • "Withered" technology = tech that is old enough to be extremely well understood and easily available so it doesn't require a specialist's knowledge.

Be a fox, not a hedgehog

  • Hedgehog experts have a deep but narrow focus. They spend their career studying a single problem.
  • Fox experts "draw from an eclectic array of traditions, and accept ambiguity and contradiction".

Learn to drop your tools and use new ones

  • "Dropping one's tools is a proxy for unlearning, for adaptation, for flexibility."
  • This is difficult to do for experienced professionals who rely on over-learned behaviour.

Be a deliberate amateur

  • Creative thinkers have an enthusiastic, childish, playful streak.

Advice on Learning

Figure out what it is you are trying to learn

  • Before tackling a problem with a given strategy, you need to figure out what the problem is. Understanding what is required to solve the problem is 25% of solving the actual problem. So, understand the problem first and then carefully choose the strategy that is best suited to that strategy.
  • "Successful problem solvers are more able to determine the deep structure of a problem before they proceed to match a strategy to it."

Effective learning is hard learning

  • Making mistakes is the best way to learn.
  • Hypercorrection effect: The more confident a learner is of their wrong answer, the better the information sticks when they subsequently learn the right answer.

Force yourself to retrieve information in different contexts

  • Struggling to retrieve info primes the brain for subsequent learning.
  • Interleaving: The more contexts in which you learn, the more you are able to take abstract ideas to apply to different fields.