101 questions to ask yourself

Asking questions is the basic and most effective tool of creativity, productivity, and happiness. When we question ourselves, we may find our true purpose. What questions should we ask? Find some examples below. For more reading see here, here, here, here, here, and here.

Annoying 101 lists

To be honest the 101 lists slightly annoy me. I provide some in the links above. They feel like a sort of endless poking with arbitrary stop rules.  In creativity exercises, there is a tool for judging the quality of a question. The question should generate a complex thought process, that like was missing from the previous considerations.

Suppose you ask yourself “What are your biggest goals and dreams?”. And the answer is “I want to be a millionaire” or “I want to be famous”.  Now what? Good questions should not enable your less creative behavior.  A marginally better question: “If this was your last day on the earth, what would you do?”  may be an opening for an all-you-can-eat feast with all-you-can-drink alcohol. Also, it looks like you asked yourself something like that.

Let us find ways to improve the perspectives…

Change the timeframe

Usually, we either consider a very short time frame, like a day or a very long one like the entire life. What if we modify the timeframe?

“You have a perfectly ordinary day three months from now. But you want to make it special, and you have these three months to prepare.  What would you like to do?”

There is no infinite amount of time or resources, and you cannot run away from responsibility. The day is not a special birthday or holiday with a commonly accepted routine, yet you want to make it different. Now you should think creatively. A similar question.

“A week from now you will wake up in the morning and decide to change one and only one habit. What will that habit be?”

You have time to decide and make some preparations, but not procrastinate.  The milestone is close, and you cannot build too many prerequisites or make complex preparations.

Change the perspective

Instead of asking “what would I want” try to projecting the wish on somebody else.

“If your child would do something for free for the rest of his life, what would you want him to do?”

Somehow this immediately shifts the perspective to legacy. What would we like to give our children? Maybe we envy something or were too afraid to try something, but our children can do this. I would like my children to play guitars because great music is a wonderful gift for everybody. Would I love to play guitar all of my life? Not really. as I prefer writing. Are my standards for myself different from the standards I want for my children?

“If your parent would die tomorrow,  what would be his biggest regret?”

I ask myself how well I know my parents. My father occasionally regrets he did not pursue anything long enough to reach true mastery. As for my mother, she always wanted to work in medicine but such a career seamed intimidating for her. I do not think I would ever regret my job, but I might regret not doing enough sports and taking good care of my body.

“How important is his job for my mentor?”

This is a classical work-life balance thing. Most mentors I know a preoccupied with their jobs and wish they had more time for other things. Yet each one is passionate about something else, and all would recommend me to pursue my passion. I am passionate about my job. What do I miss?

Change the area of application

Let us take a provocative question “Are you settling for less than what you are worth? … Why?”

We are likely to apply it many times to work, to the spouse, possibly to the place where we live. Where is it least likely to be asked? Say, volunteering activities? What is the least likely direction for this question?

In my case, I do not get as many rejections as I deserve. People generally accept and approve of what I have to offer. Maybe I am too mainstream? Should I become a bit edgier? How can I make small changes in this direction? Whom I can possibly make angry without risking my reasonably pleasant existence?

Another question “Who inspires you the most?“. Usual suspects include role models, mentors, parents. In my case, my students. What is the least plausible direction?

Most people I know are inspired by their competition, yet they hate to admit it. Our competitors share similar core values and goals and do certain things better than us. We want to improve and we are driven to change…

“Are you living your life to the fullest right now?”. I have my pleasures which I enjoy and my purpose that drives me forward. What is the unexpected thing that I miss most? Whom do I know to have it?

I am addicted to comfort, and I do not accept opportunities that are uncomfortable. For example, I would not go to a poor country with poor hygiene, and I do not seek people who suffer. But this is exactly what drives Bill and Melinda  Gates who can afford everything. Maybe there is something I miss there?


Take two unrelated questions, and try to combine them into one.

What limiting beliefs are you holding on to  [AND] who are the 5 people you spend the most time with?

Somehow this makes me think that people I am with are holding me back. Maybe I need a wider more diverse social circle?

“What are the times you are most inspired, most motivated, most charged up [AND] what are the biggest things you’ve learned in life to date?”

That’s a tough combination. How do the biggest thing I learned correlate with the things that I am motivated about? Each of these questions is hard enough, together they are impossible, unless… I love the creative feel of flow when I build something new, and I learned that boundaries are crucial for creativity. How can I change my boundaries to become more creative?

“What has always been your most natural ability [AND] what is it like to mentor others?”

I definitely do not feel comfortable lecturing others. Teaching is one of the hardest and most frustrating things for me. At the same time, I am natural in acquiring and manipulating knowledge. It would be unethical for me not to share. So mentoring for me is not a calling, but an ethical choice, which I learned to enjoy. Can I teach someone to mentor for me? Are my children old enough? Are they even interested?


Take two unrelated questions, and try to push them against each other.

“Name a subject you can speak about with genuine authority because you’ve lived it [BUT NOT] what would you do if you cannot fail?”

If I am an authority in a subject, do I feel vulnerable in it? Do I want to do something simply because I do not know what it’s like to feel there? Are my fears stopping me from becoming an authority in something new?

“How to live consciously each day [BUT NOT] how can you create new opportunities?”

The combination deals with being contained with what I already have and focusing on the opportunities that already exist. Am I too busy chasing new opportunities? What in my “low priority” list should be promoted?

“What is the most prominent quote you know [BUT NOT] when are you true to what you are?”

These subtraction questions often look like total nonsense unless I get creative. What quote do I tell every day, without actually following it? What stops me from following it? Possibly “god is in the details”. I find details frustrating and defocusing. Maybe I need to deal with that creatively. How?


Questions and confirmations are different formulations of the same thought. We can transfer one into another and still get the same result.

“What book are you in the middle of reading right now?” vs

“Read the subjects you are curious about.”


“Create your own opportunities.” vs

“What is stopping you from seeing infinite opportunities?”

As we transform confirmations into questions and vice-versa we interprete and clarify abstract ideas. We may notice something. For example, I do not really feel that opportunities are infinite as I do not have the patience for the perfect timing. If I had more patience I would create better opportunities.


How can I transcend a question? Which new dimensions can I open to do this? I will do the exercise with confirmations rather than questions.

“What is the meaning of life”

Really? How do I transcend THAT? Is there a place with no life and no meaning? There is a new scientific theory that all of our Universe is projected through a small pinhole where the big bang occurred. This reminds me Plato’s story about the shadows on the wall of the cave. The cosmologic talk takes me too far from what is relevant here and now. Maybe the truly important things are so simple and abundant that we do not notice them, like the air?

What is the most important thing missing from your life?

I feel very insecure and vulnerable. If I make a small step in the wrong direction or get unlucky, I will lose the things most important for me. This feeling is a basic part of human experience. Even the subject observing the experience changes. The only thing that does not change: I am a part of humanity with all its flaws and challenges. This makes me feel belonging and warm inside. Still very vulnerable, but in a very esthetic and positive way like a flower or a jewel. And I feel that everybody else is equally vulnerable and hence valuable.


In the links of the first paragraph, I put some sources of questions and confirmations. You can find many more online. Create 101 interesting questions for yourself using the methods above. What did you learn from this exercise? The exercise can be repeated 3-4 times per year.

questions and confirmations
questions and confirmations

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