Five Techniques To Help You Think More Deeply

Posted on June 27, 2014


I recently stumbled across a great engineering blog post:

Speeding Up Your Engineering Org, Part I: Beyond the Cost Center Mentality

that got me thinking about the various techniques I’ve come to appreciate as strategies for deep thinking. By “deep thinking” I mean “the exploration of a topic beyond superficially available information”, so instead of thinking about education by simply saying “how do we make schools better”, you ask yourself what the overall point of education is and whether schools should exist at all within that framework. Or if you were investing in startups, you may just try to evaluate each idea as it came through, or you might start to look for larger patterns and approach your investing from a specific thesis as YCombinator did, structuring an organization around the thesis to fundamentally change how you approach investing.

Now I’m not saying we should think deeply about every topic. There’s just not enough time and frequently more superficial and readily available information is good enough. When I do come across a resource where someone has thought deeply about a subject, though, I appreciate both the resource and the “deep thinker” a great deal.

In the above blog post on “speeding up your engineering”, Edmund specifically notes one strategy for thinking deeply:

One method to expose some of these invisible economic effects is to take them to an absurd extreme. For example, if your business is currently paying a half million in rent a year for a Boston office, with a workforce who lives in nearby suburbs, it’s clearly not a smart economic decision to move to a snow-cave in Juneau, Alaska—even if it’s wired for Ethernet and your annual rent would drop to $1. We’ve managed to magnify the invisible costs to a size where they can’t be easily ignored.

Taking an idea to an absurd extreme is just one of the methods I’ve found to be really helpful when thinking through ideas. Here are a few others:


This post is filled with examples for a reason. I don’t think there is any better way to talk about an abstract idea than to provide concrete examples that people can examine more closely. Another example of this is when I talk to people about how I have a certain degree of pessimism for the idea of “personalized learning”, which is frequently discussed in edtech circles. One of the arguments I provide is that it is a very difficult problem to effectively predict what someone should be learning at any given time. As an example of this I note how difficult it would be for a person to predict what kind of food another person is in the mood for or how difficult it is for Netflix to predict what movie you might want to watch right now. It’s much easier to debate the nuances of these examples and examine them for flaws than it is to examine the abstract idea in the same manner.


I recently blogged about how traditional education is like arranged marriage. The analogy provides an interesting new perspective to leverage as you think about a subject. Just like with extremes and examples, it helps to poke at the idea more effectively.

The website Better Explained also leverages analogies effectively in an attempt to make it easier to understand abstract math concepts. In this example he compares Sine, Cosine, and Hypotenuse to a movie screen hanging down from the top of a dome, providing a means of thinking about the trigonometric relationships in a more concrete manner that may be easier to visualize and manipulate in your mind.

Historical Similarities

History offers a great deal of lessons and they can be very beneficial when thinking through ideas. This is not to say that history repeats itself, but it can offer insights in to what is going on today, such as this talk about how the LGBT movement compares with the Civil Rights movement. It can be easy to draw definitive conclusions from historical similarities, such as the idea that a tablet computer isn’t a viable product because companies like Apple tried to create one in the late 1980’s, but it can also offer insights in to how such an idea may be more viable today (e.g. the tablet would be viable if it were lighter).

Experiments (including thought and blind experiments)

Let’s say you had the hypothesis that the hiring process at your company wasn’t working well. One thought experiment you could do would be to ask, “would I hire myself” to try and identify any problems in the process. An even better thing to do would be to engage in a blind experiment where you actually were given your resume but thought it was someone else’s:

Similarly, if you suspected that auditions for an orchestra seat were being influenced by the physical appearance of the person playing the instrument (especially the gender), then you might try an experiment where people auditioned from behind a screen. Such an experiment revealed that:

Using data from audition records, the researchers found that blind auditions increased the probability that a woman would advance from preliminary rounds by 50 percent.


This certainly isn’t a definitive list, but each of these five techniques (extremes, examples, analogies, historical similarities, and experiments) can make it easier to deeply analyze an idea. They can help us explore ideas from different perspectives and remove biases that may be blinding us to certain insights. Personally I deeply appreciate it when people engage in these exercises as they often lead to conclusions that I would not have recognized based on more easily accessible information.