60 Deep Questions to Ask Yourself for Real Self-Awareness

Voltaire wrote: "Judge a man by his questions rather than by his answers." There is a lot in that. A good life is not determined by what you know so much as by how willing you are to keep learning, and the most direct way to learn is to ask.

You do that all day without thinking about it. It is how you get through work and understand the people you love. The harder question is whether you are as curious about your own inner world as you are about everyone else's.

If you are, here are sixty deep questions to ask yourself. Nobody else can answer them for you. They will not produce final answers, because self-awareness does not work that way. Every time you think you have found the bottom, another layer shows up. Treat them as a compass, not a test.

What is self-awareness, and why should you care?

Self-awareness is a word people throw around as if everyone agreed on what it means. Most of us also believe we already have it. Tasha Eurich, who has studied the subject for years, found that while most people in her research rated themselves as self-aware, only 10 to 15 percent actually were.

One reason is that self-awareness has two sides, and people tend to develop one and ignore the other. Eurich describes them like this:

• Internal self-awareness is how clearly you see your own values, passions, aspirations, fit with your environment, reactions (thoughts, feelings, behaviors, strengths and weaknesses), and impact on others.
• External self-awareness is understanding how other people see you on those same points.

Knowing yourself is not only how you see yourself. It is also knowing how you come across. You need both to have an accurate picture, and the second one is the one almost everyone skips.

Daniel Goleman calls self-awareness the keystone of emotional intelligence: the thing that has to be in place before you can manage your emotions, set real goals, or handle relationships well. He breaks it into three competencies:

• Emotional awareness. Recognizing your emotions and the effect they have on you and on other people.
• Accurate self-assessment. Seeing your strengths and limits without flattering or punishing yourself.
• Self-confidence. A sense of your own worth and competence that does not collapse when circumstances change.

Each of those gets stronger when you ask yourself the right questions. And each gets stronger again when you take your answers to someone who knows you and ask whether they see it the same way. That second step is the external side. Skip it and you get the 85 percent.

60 deep questions to ask yourself

The questions are in three sets, one for each of Goleman's competencies. There are no right or wrong answers. There is only your answer, and that is the one that matters.

20 questions for emotional awareness

1. Who are you most jealous of, and why?
2. How comfortable are you talking about your feelings, and with whom?
3. What upsets you about other people's behavior, and what does that say about you?
4. How do you handle difficult but necessary conversations?
5. What demotivates you, and what helps you regain motivation after you lose it?
6. When was the last time you felt disappointed or hurt? How did you respond?
7. What is your definition of happiness?
8. In what ways are you preventing your own happiness?
9. How do you typically feel just after waking up, and when you go to bed?
10. Has insecurity ever been useful to you? What about overconfidence?
11. Are your actions mostly guided by love or by fear?
12. Do the people you surround yourself with lift you up or bring you down?
13. How often do you treat yourself with love and respect?
14. Is there someone who hurt you in the past whom you still need to forgive?
15. What regrets do you have about the past, and what worries you about the future?
16. What social situations make you uncomfortable?
17. When you look back at the past month, what was the most joyful moment you experienced?
18. When you can't sleep at night, what do you usually think about?
19. How do you feel when you see yourself in the mirror?
20. What has the fear of failure stopped you from doing?

20 questions for accurate self-assessment

1. What positive qualities do you bring to your close relationships?
2. What tasks and responsibilities do people at work trust you with?
3. What skills do you want to learn in the next five years?
4. In what ways are you contributing to your family, organization or community?
5. What activities make you feel content, energized and fulfilled?
6. What are your strategies for bouncing back after a failure?
7. What threats and opportunities do you currently see in your life?
8. What are you most likely wrong about?
9. What could you give a 30-minute talk on with no preparation?
10. Do you have any addictions? What are they?
11. What do you spend too much time doing? What do you not spend enough time doing?
12. What do you love about yourself?
13. When people come to you for help, what do they usually ask for?
14. When you ask others for help, what do you usually ask for?
15. What do you think about when you're alone?
16. What are three questions you wish you had definite answers to?
17. What is your biggest strength, and your biggest weakness?
18. If you could change one decision you made in the past, what would it be?
19. How would you describe yourself in one sentence?
20. What limiting beliefs do you hold about yourself and the world?

20 questions for building self-confidence

1. What compliment do you most like to hear, and why?
2. What challenges have you faced that you're proud of overcoming?
3. What is the mistake you learned the most from?
4. When do you say "I can't" most often, and is it actually true?
5. When was the last time you did something that scared you or made you uncomfortable?
6. What difficult problems have you solved that you first thought were unsolvable?
7. When was the last time you said "no" and felt good about it?
8. What is the one thing you would do if success were guaranteed?
9. If you could offer advice to your teenage self, what would you say?
10. What would you do differently if you knew nobody would judge you?
11. Are you on the right path in life? How can you tell?
12. What accomplishments are you most proud of?
13. When it's all said and done, will you have said more than you've done, or the reverse?
14. What changes have you undergone that seemed impossible five years ago?
15. When was the last time you felt empowered?
16. What do you need to tell yourself today?
17. What will you never give up on?
18. What is the best decision you've ever made?
19. What was the best thing you did for yourself today?
20. When was the last time you surprised yourself?

The catch: you are not a reliable witness to yourself

Here is what the research on self-awareness keeps turning up, and what twenty years of sitting across from leaders confirms. The person answering these questions is the same person whose blind spots you are trying to find. The ego is reporting on itself. A driven person believes they are authentic because their performance of authenticity has fooled even them. An easygoing person reports no strong opinions while frustration leaks out sideways.

This is why the external side matters so much, and why we work with the Enneagram at Big Self School. Not the nine-type quiz version. The Enneagram at the level of motivation: the thing that fires before you have chosen anything and then hands you a reason afterward. It gives you a map of exactly which of these sixty questions you are most likely to answer dishonestly, and in which direction. If you want to know where your own answers are least trustworthy, find your subtype. It takes about five minutes, and it will tell you which questions to take to someone else.

How to answer a deep question so it actually changes something

Asking is the first half. A question sets something in motion; answering it is what peels the layer back. How you answer matters, and each way produces something different.

Talk to someone

The hardest way, and often the most revealing. Bring a question to a friend, a partner or a colleague, or have them ask it of you, and let them watch you answer. You learn from what you say and from how you say it. Are you nervous? Proud? Bracing for a reaction? Then ask them whether they see it the way you do. That is the external self-awareness Eurich is talking about, and it is the step that turns a private insight into an accurate one.

Record it

An audio journal gets you the benefit of saying it out loud without an audience. Talking is faster than writing, and hearing yourself think when nobody is listening is its own kind of information. You can also go back and listen later, which you will find surprisingly uncomfortable and surprisingly useful.

Write it down

Writing by hand slows the mind down and makes it choose words. Do not censor and do not edit. Then leave the page for a few hours and read it back with fresh eyes. Most people find at least one sentence they did not know they believed.

Sit with it

Ask the question and then stop trying to answer it. Go for a walk, take a shower, do something with your hands, and watch what your mind produces without pushing for a result. This asks you to let go of what you think you already know about yourself, so be ready to be surprised.

Sleep on it

The chess and tai chi champion Josh Waitzkin asks himself one question right before bed, what he calls the Most Important Question, and then lets it go. The answer often arrives in the morning. Keep a notebook by the bed and write first, before the day starts talking.

Closing thoughts

A large part of how your life goes depends on how much of yourself you can actually see. If you know what makes you tick, what you are afraid of, which moments set you off and what you do next, you make better decisions and you spend your time on the right things. Not because you have become wise, but because you can finally see the consequences of your own patterns while they are happening.

The deeper you go, the clearer it becomes that you will never fully know yourself. That is fine. The answers were never the point. The looking is.

Viktor Frankl put it this way: "The meaning of life differs from man to man, from day to day and from hour to hour. What matters, therefore, is not the meaning of life in general but rather the specific meaning of a person's life at a given moment."

Ask the question that matters right now. Then take your answer to someone who will tell you the truth.