Asking yourself questions is a critical part of thinking. But it’s possible to become mentally paralyzed if you ask yourself unhelpful questions. You can easily figure out that a question is unhelpful if you do your thinking “on paper” as I recommend in the Thinking Directions Starter Kit. If you find yourself staring at a question you wrote, it’s probably not a helpful question. If you find yourself going back over the same ground, you probably are not asking yourself helpful questions.

What makes a question “helpful”? It’s answerable and it’s relevant to your thinking process.

Is it answerable by you?

It is not hard to generate questions. For example, if you are considering a major career change, you can probably generate a page of questions concerning whether you should make the change, how it would affect your life, what would be involved, etc. Easy peasy. And let’s stipulate that it would be much easier to decide whether or not to make the change if you knew the answers to all of these questions. Who wouldn’t want all of their questions answered before making a major decision?

But you probably don’t know the answers to many of the questions you pose, especially if some of them require specialized knowledge or predicting the future. It might not hurt to make a list of questions to research, but when you sit down to think, you are looking for answers, not more questions.

What thinking is

Thinking starts with a purpose — something you want to figure out. Here are some possible goals for thinking:

• to infer a conclusion about something for which you have a lot of data
• to make a decision among options
• to imagine a new possibility (as in forming hypotheses or coming up with possible solutions to a problem)
• to identify the means to some end

Unanswerable questions stop a thinking process in its tracks.

This is because thinking concerns integrating new observations with your existing knowledge and values to identify some new fact. That’s what distinguishes thinking from observation, experiment, and other cognitive processes. It involves using stored content from your own mind to create the knowledge. You don’t just look out at the world. You bring your own relevant knowledge to bear.

The questions you ask yourself during a thinking process have a specific purpose: to trigger stored information that is relevant to your thinking goal. If you ask yourself a question for which your only answer is “I don’t know,” you don’t get any new information out of your mental storehouse. You have not moved the thinking forward.

This is true regardless of why you got that “I don’t know.” Some questions could not be answered by anyone — such as, “Will it rain on July 4 in Boston next year?” Such questions are just a distraction. Some questions might be answerable with research, such as, “How much rain does Boston typically get each year?” But if you don’t have that knowledge at your fingertips, such a question will not help you with this thinking process now.

Sometimes in the middle of a thinking process, you will properly conclude that you don’t know enough to proceed. You find a pocket of ignorance that can be filled only by further exploration of the world. But a lot of people sell themselves short in this regard. If you know enough to set a thinking goal and ask some unanswerable questions, you probably have some relevant information on the topic.

First aid for “I don’t know”

What you need is a way to trigger that relevant information so you have something to work with.

When I ask myself a question and go blank in answer, the first thing I do is ask myself, “What do I know that’s relevant?” For example, I don’t know the average rainfall in Boston, but I know it rains regularly in the summer and snows regularly in the winter. The annual rainfall is higher than Albuquerque, New Mexico, and lower than Naples, Florida.

Do I really need to know the exact average rainfall? It depends entirely on my purpose in thinking. If I am selecting plants for a garden, it could be important. But perhaps I could just choose plants I already know could handle a middle-ish range of rainfall. If I need to make a decision quickly, this could be a much better option than delaying the decision while I do more research to get that specific fact. By identifying what I do know, I make it possible to reach a conclusion sooner rather than later.

Marcia Yudkin, one of my longtime mentors, likes to say, “You know more than you think you know.” You do — and asking yourself “What do I know?” is one way to access your storehouse rather than get stopped by an unhelpful question.

Is your question relevant to achieving the goal?

Sometimes the problem is not that you don’t know the answers to your questions. It’s that the questions are patsy questions. When you answer them, you just rehearse a lot of facts that you already know. This can give you a sense of going in circles and not getting anywhere.

The purpose of thinking is to figure out something new.

So, if you’re trying to decide whether to make a career change, which of these questions do you think would help you move forward versus go in circles?

1. Why don’t I want to continue in my current career?
2. What’s the urgency in making a change, i.e., on what time scale do I want to shift?
3. What might be some alternatives?
4. What’s most important for me for the next phase of my life?

Your answer is likely different from someone else’s. It depends on what you’ve already thought about and already know. If you don’t already have some idea why you don’t want to continue in your current career (question #1), you probably can’t answer question #2 about the urgency. But if you have been complaining about your current career for the last six months, you don’t need to do any more thinking about why you don’t want to continue. You already know the answer.

Similarly if you have no idea of what you might do next, you do need to spend some time generating some ideas (question #3). If you find it hard to come up with alternatives, you might need to do some general research or you might simply ask yourself question #4. Identifying what’s most important for you in the next phase of your life is an introspective thinking task. If you have experience introspecting, that would be a good next step as it would help streamline your research task. But if you are not a particularly good introspector, you’d be much better off reading some books on career changes to help you come up with possibilities.

Thinking is a goal-directed activity. Like every other goal-directed activity, you need to monitor your progress and adjust as you go. If you catch that you are asking unanswerable or irrelevant questions, don’t give up on figuring things out. Ask yourself what you do know that is relevant.