13 Painful Questions You Should Ask Yourself

There are some uncomfortable questions that you should ask yourself to get to know yourself better. However, these are the kinds of questions that can uncover certain psychological areas that you've been neglecting. Will you dare to ask them?
13 Painful Questions You Should Ask Yourself

Last update: 10 August, 2022

Some questions hurt and you prefer to avoid and not address them because they question a part of who you are. In fact, we all have sensitive areas that we don’t want anyone to touch, let alone discover. It’s as if the armor that allows you to be strong and even functional in the face of others is removed, and behind that shield hides a fragile and vulnerable self.

However, it’s healthy to bring those spaces you’ve left in the psychological shadows to light. Indeed, it’s a good idea to become aware of your fears, insecurities, emotional problems, and thought biases.

Curious as it may seem, this type of exercise was first proposed by Wilhelm Wundt, who’s considered to be the father of scientific psychology. He claimed that asking ourselves questions and practicing introspection makes it easier for us to delve into dimensions such as thoughts, emotions, and mental images that shape our narratives.

So why not make a start today? You might find these 13 simple questions really useful.

Practicing self-talk and asking yourself tough questions from time to time allows you to become more self-aware in the midst of an ever-increasing fast-paced world.

Bored boy on the sofa
Asking yourself certain questions allows you to get to know yourself better.

Painful questions that are worth asking

Reflecting on yourself and your surroundings is healthy. That said, you must get it right.

Timothy D. Wilson, a social psychologist at the University of Virginia (USA) and an expert on the unconscious mind, self-knowledge, and decision-making, makes an interesting point in his 2004 book, Strangers to Ourselves.

He claims that knowing yourself doesn’t only require you to ask yourself painful questions. That’s because you’re not only what you think, you’re also what you do. Therefore, it’s also important to ask your friends, family, and partner how they see you. It’s quite possible they may reveal aspects of you of which you’re unaware.

We suggest you begin this journey of self-knowledge and revelation by asking yourself a series of questions. You don’t have to answer them quickly. It’s not an intelligence test, it’s an exercise in reflection.

1. What aren’t you doing because of fear?

Fears are like barbed wire for your well-being and personal fulfillment. While it’s true that they often serve as a necessary survival mechanism, there are times when you give power to clearly irrational fears.

The only way to deactivate them and feel free to grow and achieve your goals is by being aware of them.

2. What’s more important to you… that others love and admire you or that you love yourself?

You might answer “Both” to this question. Of course, it’s true that happiness and satisfaction reside, in equal parts, in receiving affection from others and good levels of self-love. However, the problem is that, sometimes, you focus more on one area than another.

It isn’t healthy to depend on the admiration and affection of others to feel good. Nor should you love yourself excessively and neglect others.

3. What’s the difference between your ‘public self’ and your ‘private self’?

This is one of those painful questions that we should all ask ourselves. Do you behave the same in public as in private? Are you a social chameleon who always seeks to blend in with others to feel integrated?

Bear in mind that striving to be someone you’re not just to please and feel accepted only brings suffering.

4. Are you making an effort to meet other people’s expectations?

It never hurts to reflect on your efforts and goals and the kinds of activities to which you dedicate so much time. Nevertheless, you should ask yourself if these objectives that you’re hoping to achieve are really satisfying and thrilling to you. Or are they, perhaps, expectations of others that you’re forcing yourself to meet to satisfy others?

5. Are you idealizing someone?

You idealize others when you’re in love with them you admire them a great deal. In fact, attributing positive traits and characteristics to someone just because you like or are attracted to them is extremely common.

In these cases, there’s nothing more important than being aware of your idealization and applying a more objective look with fewer filters.

6. Do you think you’re engaging in some kind of behavior that’s negative for you?

This is another painful question to ask yourself. You may be caught up in many self-defeating behaviors right now that you don’t want to see. One example of this is stubbornly thinking that, whatever you do, nothing will improve (I won’t find a job, I won’t be able to get out of this unhealthy relationship, etc.).

Nor should you overlook behaviors such as eating disorders (ED), alcohol abuse, excessive dependence on cell phones, etc. You need to accept the fact that you’re involved in unhealthy behaviors.

7. Is there someone who doesn’t value you, but whom you can’t leave?

Friends, relatives, and even partners… In your life, there might be one or several people who don’t appreciate you as you deserve and don’t value you. Maybe it’s time for you to make a decision.

8. Do you think there’s something in your past that you haven’t yet resolved?

The field of mental health places a great deal of emphasis on the aspect of trauma. Indeed, we’re a society that carries with us many painful events from yesterday that haven’t been resolved. A childhood of abuse or lack of affection is an example. School bullying and workplace harassment are equally relevant.

Pensive woman doesn't know what to buy for dinner
Thinking about those aspects of your past that you haven’t overcome is essential.

9. Do you love and respect yourself as you really deserve?

How’s your self-esteem at the moment? How about your self-love? You must remember that these dimensions aren’t stable over time. It’s common for them to weaken or fluctuate as a result of complicated experiences. Reflect on how you feel and how you perceive yourself.

10. Do you really know how to take care of a relationship?

This is an essential question to ask yourself. Because you might be carrying dysfunctional patterns you saw in your own family. Or, perhaps you’re validating myths such as romantic love, which only brings you suffering and misunderstandings.

Relationships require daily attention, respect, good communication, and the most important ingredient of all: trust.

11. Are you blaming others for things that are your responsibility?

Not everyone will ask themselves this question. That’s because it’s difficult, uncomfortable, and isn’t always properly understood. However, in reality, you often tend to blame your family and society for what happens to you.

It may be that your low self-esteem and traumas originate from a dysfunctional family. Or perhaps you’re currently unemployed. Regardless of what’s happened to you, it’s your responsibility (and only yours) to act in the face of everything that’s happening to you.

12. Are you working on your dreams and goals or are you hoping for a lucky break?

Maybe you’re hoping that fate will bring everything that you want and desire to your door. While, at the same time, forgetting that achieving goals requires daily efforts, motivation, persistence, and planning.

13. Do you manage your emotions or do you let yourself be carried away by them?

Our list of painful questions to ask yourself wouldn’t be complete without one that delves into the subject of emotion. This is another neglected area and one in which you don’t always empower yourself as you should. It’s time to face it. How do you deal with negatively valenced emotions? Do you let yourself be carried away by anger or rage or do you know how to regulate them? Remember that effectively managing your emotions has a direct effect on your well-being.

Finally, it never hurts to have a conversation with yourself and delve into these issues. You may well realize that there are certain areas that require your attention.

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  • Galperin, A. y Haselton, MG (2010). Predictores de la frecuencia y el momento en que las personas se enamoran. Psicología Evolutiva, 8 .