I liked this book, even if it's not super practical, it's thought provoking, which I guess is the intent.


Two kinds of environment: kind and wicked. Kind has clear rules and repeatable patterns (chess, tennis), wicked has no clear rules, complex arrangements, and is hard or impossible to predict. Most of the world is wicked.

The orthodoxy wants that people get specialized and start specialization young. However, evidence shows that generalization provides more ideas and better results in wicked environments.

Some strategies and benefits of generalist thinking

Accept some uncertainty, detours, exploration, as an investment to discover. If you want the sky highs, you have to tolerate a lot of lows.


Two types of education - specialized (e.g. Tiger Woods who trained from a very early age on just golf) and generalized (e.g. Federer who trained in a large variety of sports including a ball and developed a range of corresponding skills)

Two types of learning environments - kind where things are somewhat predictable, and deliberate practice brings recognition of patterns and better results. Wicked, where rules are not clear, complex behavior is less predictable, and experience brings limited certain outcomes.

In kind environment (e.g. chess, tennis, golf), excellent tactics (i.e. raw skills) + basic strategy bring you a long way. In wicked environments, they matter less. Most environments are wicked

Specialized training in kind environment produces narrow skills. Training in more areas allows recognizing different patterns and more adaptability. these are intuitive experts. They recognize patterns, then can think about them, but usually intuition is good

Fermi approximations: approximations based on little data you know (e.g. How many Piano tuners in Chicago)


Analog reasoning is applying analogies from other fields to a problem. To be able to reason analogly requires a diversity of experience and learnings.

Diversity of experience is necessary to understand what we like. Diversity of training and jobs is desirable before committing. Advice against quitting something that does not fit with us is common and wrong. Test and learn, rather than plan and implement. Instead of working towards a goal, work from a promising situation. Avoid sunk cost fallacy.

Careers tend to go to specialization, however the concentration of experts means that all questions answered within the fields are answered, and the questions from out of the field are not.

Lateral thinking with withering technologies is looking for new uses of well understood technologies. It allows escaping the brute-force race to always try and find newer technologies, which has a lot of competition, and instead focus on actually fixing a problem (think: Nintendo).

Beware of expertise

In the face of unfamiliar challenge, don't hesitate to drop your familiar tools. Extend the set of data you consider, look for approaches you didn't consider, change the way you process data.

Deliberately reserve time for experimentation and doing different things or things in different ways

Accept some uncertainty, detours, exploration, as an investment to discover. If you want the sky highs, you have to tolerate a lot of lows.