Whatever Works

A toolkit for self optimization

5.4 Asking “Why”

Cultivate curiosity about the reason things happened.

Motivation

We all interpret the meaning of events, but unless we sincerely ask “why,” we’re bound to be blind to the circumstances leading to our present situation. At times, the reasons are obvious—you cut your finger, so you bandage it. Other actions stem from more complicated causes. Let’s say the dry cleaner ruins your favorite shirt, and you threaten to sue them. Your unexpected rage, however, might not be purely about the shirt itself but more about the memories tied to the shirt, which belonged to your recently deceased best friend.

Asking “why” requires you to be curious (Tool 5.3). Your brain is wired to explain everything that happens to you and to eliminate gaps in your understanding. When you encounter a situation, it immediately spits out a model of what has occurred, as well as how and why. Even though this model is by definition probabilistic, your lizard brain doesn’t know this. It often clings to one option and sees it as objective reality.

By taking the time and energy to dig deeper and question your initial interpretations, you open yourself up to see a larger picture and consider options that would otherwise have been hidden from your sight.

Benefits

By challenging our innate assumptions and continuously asking “why,” we expand our knowledge and illuminate blind spots in our comprehension, fostering a deeper understanding of the world around us.
This approach helps us better comprehend the perspectives of others, deepening our empathy and encouraging more meaningful, compassionate interactions.
Asking “why” allows us to defuse conflict by breaking through negative cycles of assumption and blame.

Challenges

Some assumptions and beliefs are so deeply embedded that it's hard to move beyond them.
Sometimes, people may not be able to fully explain their actions, or their account may not seem entirely trustworthy or comprehensive, leaving you to wrestle with ambiguity.
Use this tool judiciously—in certain contexts or cultures, asking “why” may appear intrusive or inappropriate.

Application

The first step to a better understanding of a person’s motives is relaxing the assumption that you already know them or that it’s ever possible to know them for sure. When confronted with a situation that you don’t fully understand, take a moment to pause and ask why things are the way they are. If you are engaged in an argument, for example, instead of responding based on your immediate assumptions or beliefs about the other person's behavior, pose a question—ask them why they chose to act or speak as they did. This response allows you to step back from your preconceptions and approach the situation with an empathetic and curious mindset, which can lead to a more nuanced understanding and foster effective communication.

If someone appears upset or angry with you, resist the urge to become defensive. Instead, gently ask them why they feel the way they do. This approach has two key benefits: it defuses the immediate tension and also provides valuable insight into the other person’s perspective, facilitating a more constructive path through the conflict.

As Socrates wisely said, “The only true wisdom is in knowing you know nothing.” This is not to encourage self-deprecation but to serve as a reminder to remain humble in our pursuit of understanding. When we question our assumptions and seek the “why,” we acknowledge the limitations of our knowledge and open ourselves to continuous learning. This humble curiosity paves the way to deeper wisdom and insight, and it all begins by asking “why.”

When asking “why,” remember to adopt an attitude of curiosity, not aggression. You’re not asking people to justify their actions; you’re seeking greater understanding of their behavior. Ask “why” as a means to encourage dialogue, enhance understanding, and nurture empathy.