Significantly Improve Your Self-Esteem By Asking Yourself These 37 Self-Esteem Questions

You’ve been beating yourself up for too long, and you don’t deserve it.

So it’s time to boost your self-esteem.

Besides, self-assured people perform better professionally and socially and are generally more comfortable in their own skin.

A sense of mental peace comes along with self-esteem — in addition to a handful of physical benefits.

How do you develop a sense of self-worth?

One way is by journaling and thinking about the topic.

To that end, let’s explore some open-ended questions about self-esteem and confidence.

The Benefits of Asking Yourself Self-Esteem Questions 

The overwhelming majority of Americans — 85% to be exact — suffer from debilitatingly low self-esteem at one or more points during their lives, according to a study by Dr. Joe Rubio.

It’s a shame because self-esteem has many benefits, including:

  • Increased Persistence: People who value their self-worth are better at picking themselves up, dusting off, and trying again after a failure.
  • Decision Making: Folks who are heavily influenced by the tide often do things they don’t want to impress folks they don’t like. People with self-esteem usually have their emotions under check and make better decisions as a result.
  • Better Sleep: When we’re pleased with our life’s trajectory, we enjoy better sleep. Why? Insomnia and other sleep disorders are often a symptom of stress and worry. But people with self-esteem tend to lead more ordered lives. 
  • Stronger Friendships and Relationships: Maintaining relationships is hard enough — but the task becomes even rockier when we’re contending with insecurity. Uncertainty often leads to foolish behavior, resulting in strained personal and professional relationships.
  • Improved Physical Health: Self-esteem helps us eat better and exercise more. Fueling the body with healthy options allows it to function better — including your brain.

37 Questions To Ask About Self-Esteem 

How does self-esteem work? Is it easy to develop?

Your exact situation dictates a lot. Some people need intense therapy to find a healthy place. Others do best with coaches, and others prefer the self-help route.

In the meantime, journaling about the topics, questions, and prompts below may help you on the path to mental health.

1. What do you do well?

We’re taught not to brag, but some people take that lesson too far and spend a lifetime berating themselves — which is equally detrimental. Positive self-talk does wonders for your self-esteem. 

2. What activities and actions give your life purpose?

Delineating your life’s purposes helps you keep moving in a productive direction.

woman looking sadly at her reflection questions to ask about self-esteem

3. How do you make others feel confident and capable? Do you grant that same grace to yourself?

We feel good about ourselves when we help others. Moreover, we can better control our emotions when we extend the same kindness to ourselves.

4. When was the last time you felt self-assured?

Recalling a time when you felt self-assured puts that feeling within reach. 

5. What are your fundamental beliefs? Have you come to them on your own, or are they an amalgamation of what others told you to think?

Autonomy bolsters self-esteem. When our beliefs are our own, we’re more comfortable in our skin.

6. Do you have a positive mantra with which you can soothe yourself when anxiety or depression descend?

Mantras can be wonderfully relaxing. Implementing one can go a long way in keeping you on an even keel.

7. How frequently do you doubt your capabilities? What about when it comes to other people?

Does a negative internal voice plague you? Staring down the demon can diminish its power.

8. What could you do to make yourself proud today?

We spend so much time worrying about what other people think of us that we forget to check in on our own opinions about ourselves.

That’s no good. After all, self-awareness is a critical component of self-esteem.  

9. How do you define personal success?

It isn’t easy to define social and personal goals without understanding what success means to you.

10. How do you define professional success?

Personal success and professional success are slightly different emotional animals. Think about your professional goals.

11.  What do other people tell you you’re good at?

How do you handle compliments? Do they go in one ear and fly out of the other? Use this prompt to remember when other people have noticed your skills and talents.

12. How do you feel about mistakes? Think about how errors can be positive and helpful.

Unpacking your relationship with mistakes is a worthwhile task. Many people discover that their fear of messing up holds them back.  

man writing on his journal questions to ask about self-esteem

13. Which people in your life improve it? How?

No rule says you must like everyone. Sometimes, there are folks with whom we don’t get along.

And then there’s the opposite side of the coin — the truly wonderful people in our lives. Considering how the second group fits into your life can boost one’s mood.

14. What are three qualities you want to have?

Visualizing who and how you want to be is an essential component of shaping your life.

15. Who embodies your ideal amount of confidence?

Having role models isn’t a bad idea, no matter your age. Think about who you admire and why.


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16. Have you ever overcome fears?

Fear is many peoples’ #1 nemesis. It holds many humans back from reaching their potential. Learning how to identify yours and overcome them will make a world of difference in your life.

17. For what are you grateful?

There’s something magical about gratefulness. Similar to volunteering, it brightens your day.

Plus, our outlook becomes more favorable when we focus on what we have instead of what we don’t.

18. What makes you valuable to the people in your life?

Go ahead and pat yourself on the back for the things you contribute to others’ lives. Don’t hold back. There’s no such thing as boasting when it comes to this exercise.

19. What steps can you take today to improve your tomorrow?

Thinking before acting is an excellent way to navigate life. 

20. Do you want to be a leader? What does it take to be one?

If you’re someone with leadership goals, brainstorm about what it takes and what you can tweak to get there.

21. Who is the most inspiring person you can think of? Why do you admire them so much?

Who rocks your world? Think about it and try to be as detailed as possible so you can take lessons from the good.

22. What is your favorite quote about self-esteem or confidence? If you don’t have one, do some research.

Language is powerful, and pithy sayings stick better than long prose. Having a few self-esteem quotes or mantras on hand can help you power through tough times or keep you motivated.

23. What are the differences between your actions and your thoughts?

We often don’t realize when our actions and ideals aren’t aligned. Inspecting your values under a microscope and comparing them to your actions can help rectify the situation.

24. Think about your relationship with compliments. Are you good at accepting them? Do they make you uncomfortable? If so, why?

Contemplation is a great way to expose your insecurities’ root causes. Not handling compliments well is a common hurdle. 

25. What would you do if you knew you couldn’t fail?

This is a powerful thought for many people that helps them overcome anxiety and other mental obstacles. If you’re contemplating taking a significant risk, this question is a useful one to ponder.

26. What type of music improves your mood?

Music has an outsized impact on the human psyche. Think about what genre makes you feel best and explore why.

27. What would you do if you couldn’t watch TV for a month?

Self-challenges are challenging but fun. Not only do they allow you to see how life would be if you eliminated a less-than-ideal habit, but they also help you shift gears.  

28. Do you have goals, or do you live life by the seat of your pants?

Take stock of how you’ve gone about life to this point. Has it served you well? 

29. Do you spend more time trying to impress other people or yourself?

Breaking the habit of pleasing other people instead of yourself can be a hard one to break. But doing so will alter your life for the better.

After all, most of the time, peoples’ opinions of you are often rooted in competition, misunderstandings, and implicit biases. 

30. Why do you care about other people’s opinions of you?

Think about why you’re preoccupied with other peoples’ opinions of you. Do the reasons serve you or hold you back? 

31. What is your best quality?

It’s perfectly acceptable to know your strengths and weaknesses — so long as it doesn’t morph into arrogance. Thinking about your best qualities can help build self-esteem.

32. What do you like best about your personality?

If you don’t like yourself, it’s difficult to appreciate other people genuinely. So think about what you appreciate about your character. 

33. Do you have friends that treat you like an inferior? Why do you remain friends?

Sometimes, we end up in unequal friendships where one person treats the other like an inferior subordinate.

man talking on the phone questions to ask about self-esteem

Has it happened to you? If so, take time to think about why you remain in the relationship. However, avoid confusing your prejudicial projections with genuinely lousy treatment. 

34. Are you comfortable with your core beliefs and values?

A large part of self-esteem is understanding your values. Consider if yours are a product of your belief system or someone else’s. 

35. What are you most curious about?

Think about what you’re most interested in. Could you turn it into a career? Or is it something you enjoy to escape work?

36. What kind of life would you lead if you knew nobody would ever judge you for anything?

Some types of judgment are corrosive, and fear of it holds us back. Think about how you would be and act if you didn’t have to worry about unhelpful, negative assessments.  

37. Write a love letter to your mistakes

Mistakes are fountains of wisdom and compassion. In other words, the more mistakes you make, the more you learn, and the larger your capacity for kindness expands. So go ahead and write a love letter to every misstep you’ve ever taken and learned from. Each one is a gem.

Self-esteem is as close to a magic potion as humans have. As long as you don’t let it metastasize into arrogance, self-esteem will carry you far, and cultivating it is an integral part of the success recipe.

Stop thinking you are less of a person. Ask yourself these questions to ask about self-esteem and boost that confidence of yours.