Self-questioning: Why Should We Practice It on a Daily Basis?

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Explore the transformative potential of self-questioning as the cornerstone of self-mastery. Discover how introspective inquiry fuels personal growth, enhances self-awareness, and empowers us to navigate life with clarity and purpose!

We often overlook the transformative power of a simple question: “Why?” Self-questioning, though easy to understand, is rarely practiced consistently. Yet, this act is a true catalyst for positive change. It’s more than just introspection; it’s a “magic move” that has the capacity to unlock massive growth and empower us to navigate life’s complexities with greater clarity.


  • Self-questioning is the act of objectively examining your actions, motivations, and assumptions to gain self-awareness and improve future decisions. It is a curious exploration for growth – unlike self-doubt, which is just a paralyzing fear of inadequacy.
  • Many people find it hard to adopt this practice due to reasons such as lack of awareness, resistance to change, and negative thought patterns. However, you can overcome this issue by cultivating a growth mindset.
  • Self-questioning involves starting with basic questions, then delving deeper with open-ended prompts, considering opposing viewpoints, reflecting, and being kind to yourself throughout the process.

What is Self-questioning?

Self-questioning involves an objective and non-judgmental examination of one’s actions and the underlying motives behind them. At its core, it is about asking thought-provoking questions that delve into your core values and beliefs, with the aim of fostering self-awareness and personal growth.

Examples of self-questioning prompts:

  • What was I thinking at that time?
  • Did I react based on rational thought or emotional impulses?
  • Could I have handled the situation in a different way?
  • How do others think about my actions?
  • etc.

Self-questioning is more than just a retrospective analysis of past actions. Its main focus is to explore the assumptions and motivations that drive those decisions. Why did you think your course of action was the most optimal? Are there alternatives you haven’t yet considered? Have unconscious biases been influencing your choices? Are there other solutions that you might have overlooked? These are just some of the questions that self-questioning seeks to address.

decisions in life

Benefits of Self-questioning

Enhance self-awareness

Consider this scenario. You’re at work and have just finished a presentation. A colleague offers a negative comment. In response, you find yourself bristling with defensiveness and anger.

Upon reflection later, you may ask yourself:

  • “Why did I react so strongly?” Perhaps you then recognize that the criticism tapped into feelings of insecurity about your presentation, or that the colleague’s tone of voice was disrespectful.
  • “What prompted my emotional response?” It’s possible that your sensitivity to criticism, coupled with a reluctance to accept feedback, was the thing that fueled your reaction.

As you may see from the example above, through self-inquiry, one may unearth the underlying emotional and habitual triggers behind their behaviors. Such self-awareness empowers them to make more informed choices in the future. For instance, you might decide to revisit the situation with your colleague to gain a deeper understanding of their perspective.

Release emotions

At various points in life, we all encounter emotional hurdles that leave us feeling “stuck”. Whether triggered by significant events like the loss of a loved one or the end of a relationship, these emotional upheavals may prompt us to retreat and shield ourselves from the pain. While this coping mechanism offers temporary respite, over time, it will result in the establishment of “invisible psychological barriers” that isolate us from others and render us numb in terms of emotions.

Self-questioning is a potent tool for navigating through such emotional impasses. Being aware of our present state, we can pose probing inquiries like:

“Why do I find myself emotionally immobilized?”

And then after introspection, we may respond with something like:

“I realize I’ve lost touch with my emotions – sadness, anger, joy. In avoiding the pain of loss, I’ve inadvertently stifled my ability to process and release these feelings.”

Through self-interrogation, we open avenues for emotional release and healing, thereby gradually dismantling the barriers that encase our emotions and fostering a more authentic connection with ourselves and others.

Challenge assumptions & broaden your horizons

The practice of self-questioning serves as a catalyst for challenging our assumptions and biases. Instead of being reluctant to embrace new perspectives or regularly indulging in negative self-talk like “I can’t do it,” we shift our mindset to one characterized by openness, multidimensional thinking, and optimism. Indeed, studies have revealed that those who engage in the practice of self-dialogue demonstrate a 3x capacity to learn compared to others.

By actively questioning our own beliefs and preconceptions, we create space for alternative viewpoints and possibilities to emerge. This process of cognitive exploration broadens our horizons, as well as fosters a deeper understanding of ourselves and the world around us.

Promote critical thinking & problem solving

By examining situations through various lenses and addressing questions such as “Is there evidence to support this claim?” or “How can I counter this viewpoint?”, we not only deepen our comprehension of the subject matter but also sidestep cognitive pitfalls. In addition, this practice prompts us to break down complex issues into manageable parts, which facilitates more effective decision-making.

Gain insights into your core values

Many of us (I myself too) often fall into the trap of multitasking; we are too eager to check off tasks on our to-do lists while inadvertently neglecting meaningful interactions with others. But is this truly the path we wish to pursue?

Honest introspection allows us to uncover deeper insights into our core values and priorities. We may then come to realize that our true worth cannot be measured by the completion of tasks alone. Work, wealth, fame, accolades, etc. do they truly matter to you? Or is it familial love, meaningful relationships, life balance, and altruism that you truly hold dear?

As you can see, by probing our motivations and aspirations, we gain clarity regarding the values that truly resonate with us. Are we driven by external validation and material pursuits, or do we prioritize intrinsic fulfillment and genuine human connection?

Track personal progress

Let’s say you decide to learn a new language, with the goal of achieving conversational fluency and basic reading comprehension. Along the way, you pause to reflect and think: “Can I confidently greet others and introduce myself now?”

Upon introspection, you may realize that while overall you are doing fine, there’s an issue with vocabulary retention. At this moment, you wonder: “Is my current method of memorizing word lists effective, or would utilizing flashcards be a better approach?”

As you can see from the example above, continuous self-questioning is crucial to keeping track of your own development, identifying your current strengths and weaknesses, and deciding on strategies for adjustment accordingly.

Improve interpersonal relationships

Self-questioning serves as a valuable tool in nurturing emotional intelligence and fostering meaningful social interactions. By engaging in introspection, one may uncover the root causes of their negative emotions and come up with healthy coping mechanisms. On the other hand, the process also facilitates a deeper understanding of the impact of one’s actions on those around them.

For instance, you are enjoying a cup of coffee with a friend, who appears distant and subdued. Rather than hastily attributing their demeanor to personal offense, you pause to ask yourself:

  • Have I inadvertently said or done something that may have upset my friend?
  • Could there be external factors that impact their mood?

With genuine concern and empathy, you then extend a supportive hand:

“Is everything alright? You seem a bit preoccupied.”

Just one subtle shift from reactive assumption to empathetic inquiry like that can profoundly enhance the quality of our relationships.


The role of questioning yourself in life

Self-questioning vs Self-doubt

Self-questioning is often mistaken for self-doubt; however, there are key differences between the two concepts. The former is like sharpening a pencil; you assess the current state (blunt tip) and take steps (sharpening) to improve its function. On the other hand, the latter is like snapping the pencil in half; it renders the tool unusable and hinders your ability to write (achieve your goal).

Here’s a more detailed breakdown:

FocusExamines your actions, motives, and beliefs
Questions your abilities and worth
GoalGain a deeper understanding and potentially improve
Often negative reinforcement, can lead to inaction
FeelingCuriosity, openness to new perspectives
Uncertainty, insecurity, anxiety
OutcomeFacilitate growth, better decision-making, and emotional intelligence
Paralyze you, hinder performance, and damage self-esteem
Example“Why did I say that? Maybe I could have phrased it more kindly. Next time, I’ll try a different approach.”
“I’m not good enough to apply for that job. They’ll see right through me.”

Types of Self-questioning

  • Situational: Examining our motives and thought processes in a specific situation. (e.g., “Why did I react that way?” “Could I have handled this differently?”)
  • Belief-based: Questioning the underlying assumptions behind our beliefs. (e.g., “Is this belief truly serving me?” “Are there alternate perspectives?”)
  • Goal-oriented: Evaluating our progress towards our goals and making adjustments if needed. (e.g., “Am I on the right track?” “What obstacles are hindering my progress?”)

Challenges of Self-questioning

  • Lack of awareness

One significant hurdle is the lack of awareness regarding the advantages of self-questioning. Many of us may not fully be aware of the transformative potential of this practice. Educators, coaches, and mentors play a pivotal role in disseminating knowledge about self-questioning and encouraging its application in daily life.

  • Resistance to change

Humans are creatures of habit; we are inherently resistant to embracing new behaviors or perspectives. Integrating self-questioning into one’s routine requires overcoming inertia and embracing a willingness to explore unfamiliar territory. For some, this transition may require time and patience before they can truly acknowledge the value of self-inquiry.

Read more: Habits in Personality Development – A Comprehensive Guide

  • Negative thought patterns

Our minds are susceptible to negative and self-defeating thought patterns, which undermine the efficacy of self-questioning. Too often, we are plagued with questions that cause feelings such as anxiety, doubt, and insecurity. For example:

  • “What’s wrong with me?”
  • “What is going to happen?”
  • “How can I get out of the current situation?”
  • etc.

Instead of getting stuck with those negative thoughts, it’s essential to identify the underlying motives behind them (e.g. fear of failure or uncertainty) and address them through techniques like building self-confidence and cultivating mindfulness.

For instance, let’s say you just got out of a disappointing job interview. Rather than succumbing to self-criticism, reframing the experience should allow for constructive self-dialogue:

  • Negative thought: “Why couldn’t I answer the employer’s question? I was such an idiot.”
  • Positive reframe: “I realize I wasn’t adequately prepared for that question. I’ll use this experience to better prepare for future interviews and focus on areas where I need improvement.”

By shifting the focus from self-blame to constructive reflection, we can harness the power of self-questioning to navigate challenges and propel ourselves forward on the path to personal and professional fulfillment.

Self-questioning Strategies & Activities

  1. Start from the basics

Embarking on the journey of self-questioning begins with simplicity. By asking straightforward questions about our experiences or thoughts, we lay the foundation for deeper introspection and personal growth.

Let’s say you recently had a conversation with a friend. Ask yourself:

  • “What did I do to positively influence the conversation?”
  • “In what ways can I enhance my communication skills to better express myself?”

These initial inquiries serve as catalysts for heightened self-awareness; they prompt us to scrutinize our actions and thought patterns with greater clarity.

  1. Ask probing questions that encourage analysis & introspection

The next phase involves delving deeper into the underlying principles that guide our thoughts and actions. This entails posing more incisive inquiries to unravel the intricacies of our decision-making processes and behaviors.

For instance, if you make a mistake in the workplace, engage in self-examination by asking:

  • “What factors contributed to my mistake?”
  • “How did my underlying assumptions influence my decision-making?”

These probing questions illuminate the cognitive and emotional underpinnings of our actions; hence, they enable us to gain invaluable insights into our thought patterns and motivations.

It is recommended that you pose open-ended questions that foster expansive thinking and creativity. By exploring hypothetical scenarios and alternative perspectives, we stimulate innovative problem-solving and broaden our cognitive horizons.

For example, when confronted with a challenging dilemma, challenge yourself with questions such as:

  • “What if I approached this issue from a completely different angle?”
  • “How might a shift in perspective alter the outcome?”


Metacognition in self-questioning

  1. Consider opposing viewpoints

Expanding our horizons and refining our self-questioning abilities involves actively engaging with perspectives that challenge our own. Question yourself with something like:

  • “How might people in a different circumstance interpret this situation?”
  • “If someone were to disagree with my stance, what arguments might they present?”

By immersing ourselves in alternative viewpoints, we not only cultivate empathy but also uncover the limitations of our own perspectives.

  1. Reflect and learn

The efficacy of self-questioning is greatly enhanced when coupled with deliberate self-reflection. Allocating time for introspection allows us to review our responses and assess their alignment with our values and objectives. This critical self-appraisal serves as the foundation for identifying areas of growth and refining our future actions.

  1. Show love to yourself

The goal of self-questioning is not to critique or belittle yourself, but rather to embark on a journey of self-discovery and growth. Rather than succumbing to self-criticism or judgment, you should approach the process with kindness and understanding. Here are some strategies to infuse self-love into your practice:

  • Reframe negative self-talk

When faced with self-defeating thoughts, reframe them into constructive inquiries. For instance, instead of saying “I’m terrible at public speaking,” ask yourself “How can I improve my presentation skills?”

  • Embrace a growth mindset

Rather than succumbing to thoughts like “I can’t do this,” remind yourself that while the task may be difficult, you are capable of experimentation and learning.

  • Focus on solutions

Redirect your attention from dwelling on limitations to identifying proactive solutions. Rather than questioning your abilities with doubts like “Can I do this?”, shift your focus to actionable steps that increase your likelihood of success.

Read more: Learning to Love Yourself – 16 Handy Tips for Fostering Self-esteem Every Day

The Daily Questioning Process by Dr. Marshall Goldsmith

Here, I would like to introduce you to a technique named “The Daily Question Process” – which was initially proposed by world-renowned executive coach Dr. Marshall Goldsmith. This is a self-reflection tool to assist you in tracking your progress toward your goals and living in alignment with your personal core values.

  • First, list down 32 questions (this can be adjusted as you wish) every day on an Excel sheet. These can be either Yes/No questions or require you to rate on a scale of 1 to 10; and they can cover any topic (e.g. happiness in life, relationships, exercise, eating, sleeping, etc.)
  • The trick here is to start each question with the phrase “Did I do my best to…?” This way, you will ensure personal accountability for everything you do.
  • Ask someone else to listen to your answers (in a non-judgmental way).

Through this process, you will be able to identify areas for improvement and focus on what’s truly important to you.

Read more: Daily Life Hacks to Simplify & Level Up the Day

Questions to Ask Yourself

For those who are interested, here is a collection of 200 self-reflection questions that cover a wide range of topics – including self-worth and other related domains in life.

Self-questioning Quotes

Self-transformation commences with a period of self-questioning. Questions lead to more questions, bewilderment leads to new discoveries, and growing personal awareness leads to transformation in how a person lives.

Kilroy J. Oldster


The unexamined life is not worth living.



He who knows others is wise; he who knows himself is enlightened.

Lao Tzu


The greatest challenge in life is discovering who you are. The second greatest is being happy with what you find.



Doubt kills more dreams than failure ever will.

Suzy Kassem


Final Thoughts

While self-questioning may initially feel uncomfortable, it’s a practice worth embracing. By regularly turning the lens inward, we gain the courage to challenge assumptions, refine our approach, and ultimately unlock our full potential. So next time you face a decision or experience an unfamiliar emotion, remember the magic of “Why?”. It’s the key that unlocks a world of self-discovery and empowers you to chart your course with greater wisdom!


4 Questions to Stop Asking Yourself.

The Daily Question Process.

Other resources you may be interested in:

Let’s Tread the Path Together, Shall We?

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