Why? 3 Ways Asking Questions Transformed My Life

Why Me?

Why am I here?

For many months, I set aside a few minutes every day to ask myself this question, Determined to discover the source of my soul, I entered further into my inner awareness, cutting through confusion and uncertainty with the sharp blade of concentration.

First, I was a writer. Then, I was a teacher, and then I was an entrepreneur. I was a creative artist, a self-sacrificing builder, and a visionary leader. I was a thinker. I was a doer. I was both. I was everything. I was nothing. I was confused.

My existential excursions always circled back to this original ambiguity; over and over again, I shattered my identity as I searched for an unreachable, unreal version of myself. Instead of paralyzing myself inside of a familiar caricature, I surrendered and accepted my fate. I would never discover who I was. For the rest of my life, I would float through the fog like a wandering gray blob.

My despair hardened into frustration. Why couldn’t I squeeze myself into a standard, labeled box like everyone else did? Why couldn’t I accept a simple, surface-level reality? Why did I always dig deeper? Why did I always ask questions?

Finally, I understood. Emerging through this anguish, I tasted the sweet realization; rising up from a dungeon of doubt, I unraveled the riddle to reveal the answer hidden in the question. In a moment of insight, the light of truth flickered. I was here to ask why.

Through asking why, I transformed. Through asking why, I broke through layer after layer towards the source of life and growth. Through asking why, I accepted limitation, redefined my relationships, and generated wisdom.

Accepting Limitation

Asking why was my first step to real humility. Buried in every “why” is the critical admittance of “I don’t know,” and thus every why implies vulnerability.

A few summers ago in upstate New York, some friends and I went out to a field to lie down flat on the grass, and stare up at the night sky. As a patch of clouds broke up, thousands of stars spotted the black emptiness. Shrinking, sinking into the soft soil, I felt small and powerless. Swallowed up by the infinite darkness, I encountered the hard truth. I knew nothing. ​


​ We, humanity, know nothing. Physicists don’t know what 80% of the universe is made of. They call this “dark matter.” Biologists don’t know how organic life sprang into existence. They call this “prehistoric soup.” Evolutionary geneticists don’t know how Homo sapiens developed two nostrils. They call this “random selection.”

Science, I supposed, described how the universe worked, not why the universe worked. Logic was limited. I couldn’t map my life experiences over a grid; I couldn’t upload my consciousness onto a hard drive. I was more than a robotic monkey. I was a human. I was a questioner.

For many years, I wrote down all of my questions about life, truth, self, and anything mysterious. With the guidance of my teachers and mentors, I pushed past the periphery of my understanding to absorb and digest ancient insight.

Fortunately, during my mission to define the metaphysical, I uncovered a foundation of faith. By embracing the necessary cycle of confusion and clarity, paradoxes no longer slowed my progress – on the contrary, uncertainty fueled my curiosity. Reaching for my unanswered questions, step-by-step, I climbed up higher into the rabbit hole.

I accepted limitation. I would never fully understand the complexity of even one ant or raindrop or musical note. I would never understand the absolute truth. I would only taste a trace. I would only catch a glimpse of light between the passing patches of cloud and fog.

Entering the mystery, I ascended into a world of infinite awe and wonder. Although my life was a mere speck of ink on the cosmic portrait, each day of my life contained its own universe – each moment was pregnant with purpose. After twenty years of watching the night sky, I understood a fundamental insight. My soul – like a star – was an indestructible fire of truth illuminating the vast void of chaos and darkness.

Redefining Relationships

Asking why was also my first step to real relationships. By questioning assumptions, I uncovered deeper dimensions in my personal service to others.

After my first year in yeshiva, I returned back home to an alien environment. My friends and family had changed; they expressed unfamiliar values, concerns, and motivations. American culture had changed; constantly barking into colorful, rectangular boxes, people guzzled this strange, oil-black, liquid fuel. In truth, I was the one that changed. After hundreds of hours of analyzing complex, profound texts, I had forged and refined a clearer lens to interpret the language of life.

With a deeper understanding of my own intuitive, moral conscience, I reevaluated my relationships. What did my friend really want? Where was he coming from? Which attribute motivated and sustained his challenges and goals? With patience, I decoded what he said into what he meant.

How would I help? Often, listening was enough. One word or sentence at the right time was enough. Instead of spitting out ambiguous opinions and familiar clichés, I calculated my responses. My intention shifted completely. No longer did I ask myself, “What should I tell my friend?” Now, I asked, “What does he need to hear?”

The wisdom of why transformed my whole perspective – like an x-ray, the vision of my intellect penetrated all surfaces. Digging deeper, I traced values and philosophies back to their roots. Almost always, I observed, educated people constructed sophisticated arguments and proofs to justify an assumption based on emotion or intuition; almost no one sorted out the truth in clear black ink on blank white paper.

Through wisdom, I redefined my relationships. My goal was to give, guide, and grow through objective consideration, building trust, and selfless action. My goal was to question my role. How would I give to the other? How would I receive? How would I develop stronger, deeper, more meaningful connections? In a short time, these small, inner adjustments stimulated massive, inter-personal transformation.

Generating Wisdom

Finally, asking why was my first step to real wisdom. By exploring the questions that bothered me, I unlocked the deeper chambers of my intellect.

Where was wisdom? Where was truth? Where was insight? I needed more than answers. I needed a map. I needed a process.

I stopped consuming, and I started creating. I stopped reading books, watching movies, and travelling so much. I stopped searching, seeking, and exploring. Instead, I reversed inward the flashlight of my concentration. I started free writing, logging my daily activities, and listing my principles and goals. I started asking myself hard questions. I started thinking.

How would I think better, clearer, and faster? How would I think more positive, productive, and proactive? The more I examined my thoughts, the more I illuminated the darkness of cognitive conditioning. The more I controlled my attention, the more I shaped my reality.

Through this crystallization, I entered into wisdom. Wisdom was like nuclear physics. Every true idea was an atom, and this immense, invisible energy either would wipe out civilian populations or fuel power plants. How would I use my wisdom? Would my ideas build or destroy cities?

I entered into truth. Truth was like medicine. If administered at the wrong time, or to the wrong person, the healing drug would become a poison. Too much truth could destroy another’s self-confidence, happiness, and even sanity. How would I deliver and withhold the truth to help others?

I entered into insight. Insight was like lightning. In brief moments, bright flashes illuminated my entire psychological landscape, and I identified my emotional and intellectual assumptions. How would I hold onto these fragments of awakening? How would I convert this inspiration into action?

Through wisdom, truth, and insight, I entered into reality. As I sharpened and refined my questions, they disappeared, and the puzzle pieces of my obligation snapped into place. Clarity morphed to joy, and then solidified into habit; through habit, I upgraded into myself 2.0, wiped clean of all previous bugs and glitches.

I Know Why. But What Now?

I was here to ask why. But why was I here to ask why? Was there a downside or danger to asking why?

Sometimes, asking why was unpleasant or frightening. As I penetrated my subconscious, blocked and forgotten pain resurfaced; ugly, raw reality cracked all illusions of peace and stability. Sometimes, asking why was paralyzing. As I coordinated and calculated my direction and pace, I lost momentum – one after the other, my peers passed forward on their paths to achievement and recognition.
Although asking why was hard, it was a necessary sacrifice. I refused to remain an undefined, gray blob. I wanted purpose, not pleasure; I wanted long-term growth, not instant gratification. To plant and cultivate my questions, I gave up money, respect, and sleep. To acquire my indestructible identity, I let go of all comfortable assumptions.

I was here to ask why. But didn’t everyone ask why? How was I different?

For me, asking deep questions wasn’t a mere thought experiment, meditation, or mindset. Asking why was my life. A relentless curiosity colored all facets of my personality, relationships, and activities; I asked the questions no one else cared about. Asking why distinguished me from others.

For everyone and everything, the essential component of identity is that which distinguishes one from the rest. What distinguishes you from others? What have you gained from asking why? What are your questions? Please share.


Erin shows overscheduled, overwhelmed women how to do less so that they can achieve more. Traditional productivity books—written by men—barely touch the tangle of cultural pressures that women feel when facing down a to-do list. How to Get Sh*t Done will teach you how to zero in on the three areas of your life where you want to excel, and then it will show you how to off-load, outsource, or just stop giving a damn about the rest.

4 Responses to Why? 3 Ways Asking Questions Transformed My Life

  1. Thanks for sharing! I really appreciate the insight as we can all continue to gain perspective as we grow. Redefining relationships is especially helpful as navigating relationships can be the most difficult and the most rewarding.

  2. Tutoriage says:

    Thank you for this article. It is interesting. Everyone have to ask such questions to change lives. It could help to fix many life aspects.

  3. Alex says:

    This was really great. I had overcame some really bad habits in my life and this really would help anyone who is struggling and don’t know where to go from where their at. https://bit.ly/2LIWyWV

  4. Elisabetta says:

    Asking questions is an art and can help and help you reach your goals! Great Article!

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