June 10, 2019

Whenever we start learning new things, there’s often way too much to cover. For me, I think this was most pronounced when I started software engineering as a recent college grad. With almost no prior industry experience, I was trying to understand the product, how our systems fit together, our tech stack, and coding best practices. It’s actually quite easy to forget how much surface area you get exposed to.

Faced with all of this stuff to learn, we tend to approximate. We figure out rules of thumb and invent our own patterns that allow us to get something done. We copy what others have done, treating it as the proper thing to do. Something is considered correct because simply because “that’s the way it is.” Sometimes others are the ones telling us how things are, sometimes we’re making assumptions as to how things are.

This is okay, and a completely natural part of learning. However, over the weeks, months, and years, these assumptions eventually become engrained as habits. Whenever we perform a task, we’ll default to our autopilot —the way we’ve always done things.

This autopilot is useful when our habits continue to work. In other words, when our underlying assumptions continue to be true. We don’t have to worry about the details—things will be okay because they’ve always been okay.

This autopilot can become annoying, tedious, or harmful when our habits no longer apply. Maybe our underlying assumptions weren’t completely correct. Maybe our situation or environment has changed, making our original assumptions irrelevant.

An Example

Whenever I cross the street, I check if there are any cars. I was taught to look left, then right, then left again. If things are clear, I cross the street.

However, this is intended for two-way streets where cars drive on the right side. When I look left, I’m really looking for oncoming cars on the side of the street closest to me. In country where cars drive on the left side of the street, such as in Japan, I should actually be looking right, then left, then right again.

In this case, it’s just a minor inconvenience. My autopilot will have me look left first, and I’ll just have to remember to pay more attention to my right.

Gaining Depth

There’s many situations where it’s useful to reevaluate and fine-tune your autopilot. The one I’m most interested in is when you’re trying to deepen your skill or knowledge in an area.

Regardless of what area it is, I’ve always found that improving my autopilot requires questioning why I do or believe the things that I do. That’s because I originally had to make assumptions and learn heuristics in order to reduce the complexity of what I was trying to learn. But once I’m ready to handle more complexity, I’ve often forgotten the assumptions that I made.

A natural conclusion here is that you can deepen your knowledge by challenging your assumptions. However, this is quite hard, almost by definition. If it’s an assumption you’ve engrained, it’s difficult to uncover it. Here are a few strategies that I use.

Ask Why, Relentlessly

In other words, the toddler strategy. Ask why you do things a certain way, and ask for everything you can think of. You want to uncover the areas where your answer is “I don’t know”—these are the places you’ve made assumptions. Investigate those.

Not everything you investigate will teach you something new. Sometimes your answer will be “it has to be done this way” or “there’s no better way to do this.” These are acceptable answers, if true. Be aware, however, that these are sometimes “I don’t know” in disguise.


One of the coolest and most frustrating things about people is that they learn things in different ways. When it comes to assumptions, it’s likely that others have made a different set of assumptions than you did. You want to contrast how you approach things to how others approach them, paying the most attention to where and how you differ.

From there, figure out why you differ. This might reveal ways in which your assumptions were wrong.

If you have access to the other person, you can also ask them why they do things the way they do. This is especially helpful if you can’t figure out why they do things the way they do.

Finding Annoyances

Sometimes, your bad/inaccurate assumptions have annoying or painful side effects. Pay attention to these! Don’t accept the tedious or frustrating things you do as just “things that have to be done”—figure out why they have to be done. Identify what sucks about your current situation, and backtrack to figure out why it happens. This helps lead you back to the assumption that you can improve.

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