How to Think

Bad Questions Create Bad Thinking

A lot of people think more than enough. The issue is that their thinking is organized around questions that are too vague to be useful.

When you ask a bad question, you usually get a bad answer because the question does not give your mind anything clear to work with. It sends you searching for certainty inside a concept you have not even defined yet.

A good question gives your thinking a direction. A bad question turns thinking into rumination.

Why “Am I in Love?” Is a Bad Question

Take a question like: “Am I in love with her?”

The problem with this question is that love is too broad to answer cleanly. One person means chemistry. Another means peace. Another means attachment. And yet, we act like everyone is talking about the same thing.

So when someone asks, “Am I in love with her?” they are usually trying to answer a question that has not been defined well enough to be answered.

The word "love" is doing too much, which makes the thinking cloudy.

Better Questions Define the Thing

A better version would be:

Do I see my life with this person?

Do I respect them?

Would I want my future kids to be raised by them?

Do I enjoy speaking with them?

Am I attracted to them?

Do people I respect and admire also like and respect them?

These questions are better because they break “love” into parts you can actually evaluate. Love is not one feeling. It is made up of desire, respect, admiration, compatibility, trust, friendship, shared values, and a hundred other things.

The better question helps you see the thing more clearly.

The Same Problem Happens With Career

People ask, “How do I know if this career is right for me?”

Again, too vague.

“Right for me” can mean money, status, freedom, meaning, stability, creativity, identity, lifestyle, or avoiding the disappointment of your parents.

Better questions:

Does this work give me energy more often than it drains me?

Does this career fit the kind of life I actually want to live?

Am I willing to tolerate the boring parts of this job?

Do I respect the people who are five to ten years ahead of me in this field?

Does this path make use of my strengths?

Would I still want this if nobody was impressed by it?

“Am I Happy?” Is Usually Too Vague

Another one people ask all the time: “Am I happy?”

Also not a great question.

Happiness is too slippery. Some days you are tired. Some days your nervous system is fried. Some days your life is objectively good but your brain is being dramatic.

Better questions:

Do I like how I spend most of my days?

Do I feel proud of the way I am living?

Do I have people I can be honest with?

Am I avoiding something I know I need to face?

Do I have enough challenge, connection, rest, and meaning?

Is my life aligned with what I say I value?

These are better because they move you from mood to structure.

How to Ask Better Questions

Start by noticing the words that are too vague and ill-defined.

Love. Happy. Successful. Ready. Right. Enough. Toxic. Fulfilled. Confident. Worth it.

These words are not useless, but they are usually too broad. When a question depends on one of them, define the word before you try to answer the question.

Instead of asking, “Am I successful?” ask, “What would success require me to sacrifice, and am I willing to make that trade?”

Instead of asking, “Am I ready?” ask, “What information or skill am I still missing, and can I begin without it?”

Instead of asking, “Is this worth it?” ask, “What will this cost me, what might it give me, and which tradeoff can I live with?”

Rumination tends to grow when the question is too vague. Once the question gets sharper, the answer usually becomes easier to face.

The quality of your thinking is often limited by the quality of the question you are asking.

Hack of the week: Flip a Coin

If all the advice in this newsletter fails, flip a coin.

While it is in the air, pay attention to which outcome you are hoping for. A lot of the time, the decision becomes clear before the coin even lands.