Probing Questions (#391)

Discover a list of inward-facing questions everyone should ask themselves

Aug 03, 2023

Since childhood, I have always been characterized by my curiosity and eagerness to ask questions. A notable response I have heard often is, “no one has asked me that question before.”

In my experience, that response has one of two tones. The positive-toned version is one of the greatest compliments someone can pay me. But the other version is more incredulous or irritated. In the latter cases, I often reply with another question: “Does that mean it’s not the right question to ask?”

As much as I love asking other people questions, I have come to realize that the most important questions are often the ones we ask, or don’t ask, ourselves. This is especially true if those questions challenge our closely held beliefs or assumptions.

I recently came across a thought-provoking list of introspective questions from Morgan Housel. Housel is the author of The Psychology of Money, one of the best books on personal finance I have ever read, and he has become one of my favorite writers and a widely respected thought leader. He published the list of questions as a fairly non-descript blog simply titled “A Few Questions.”

If you read some of Housel’s questions below, you’ll quickly see why this post has been shared all over social media.

Whose life do I admire that is secretly miserable?
What do I believe is true only because believing it puts me in good standing with my tribe?
Which of my current values would be different if I were raised by different parents?
What do I think is ambition (a good trait) but is actually envy (a terrible one)?
What annoys me about other people that I sometimes do myself?
How much of my nostalgia is a false or incomplete memory of the past?
Is this thing I’m worried about actually a problem, or am I looking for problems to worry about because they make me feel in control?
What is partially true but I believe in it so absolutely, and take it so seriously, that I’ve turned it into a dangerous belief?
Are there things going well in my life today that I will look back on and wish I had quit while I was ahead?
Is there something in my life I think I’m “passionate” about or “focused” on but I’m actually just addicted to it?

I love several things about this list of questions. First and foremost, asking them requires us to be vulnerable with ourselves, which is never easy. The questions emphasize the importance of authenticity, critical thinking, cultural understanding and recognizing the illusion of control.

More specifically, Housel’s questions are framed in a way that forces us to be honest about some of our more unreasonable beliefs or unseemly thoughts. It’s often through this type of radical self-honesty that we learn and grow the most. I spent some time thinking deeply about a few of the questions and suggest you spend time doing the same.

When we confront our own beliefs, biases, and narratives head-on, we often see discrepancies between the way we see the world—or our place in the world—and the reality of things. I have always loved the phrase “strong opinions, loosely held” and believe that if we want to avoid falling prey to group think and confirmation bias, we must constantly challenge our beliefs in order to evolve them. This is especially necessary as facts and circumstances change—it’s crucial to know when the evidence on a topic has shifted against your entrenched opinion on it.

Housel’s questions also connect to our sense of purpose and our understanding of what we want most. In particular, his first question, “Whose life do I admire that is secretly miserable?” is a great prompt to help you recognize if you are climbing a personal or professional mountain that will leave you feeling empty at the top.

Housel’s questions are designed to pull us out of our comfort zones and into the realm of the uncomfortable truths that are necessary for growth. The reward for this sometimes-painful self-analysis is a more balanced and informed perspective, and ultimately, a deeper sense of self awareness.

This week, take a few minutes to answer one or more of the questions, and encourage someone close to you to do the same. Your own answers may surprise you the most.

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