10 Philosophical Questions that Challenged Me to My Core

Challenge yourself with these 10 questions

The Socratic method of asking questions is what leads you to learn and experience powerful personal growth. The man himself is famous for saying, “The highest form of human excellence is to question oneself and others.” The goal of this questioning is to get to the core of who you truly are, why that matters and what you can do with that new information.

Throughout my adult life, I’ve continued asking myself the philosophical questions that have led me to become a full-time entrepreneur, bestselling author, keynote speaker, husband and father of three. In the coaching work I do with exceptional leaders, I’ve found their success is tied to asking very difficult questions and coming up with answers that lead to their purpose and direction forward.

Herein are 10 philosophical questions that have changed my life and challenged me to get uncomfortable, grow, move and make progress without making excuses. I hope you find enormous benefit in these.

This is a question about a process of elimination and identifying things that do not fit your lifestyle or definition of success. It’s also a deeper dive into limiting beliefs you may have that are affecting your thoughts and words and thus inhibiting your actions. Here’s the thing — life isn’t always a game of offense and adding things onto your plate.

It’s about removing, eliminating and mitigating things that are holding you back from happiness, fulfillment and achievement of your goals.

The quicker you can identify these things, analyze them and process them, the better you will be. They become the threats and obstacles to success you want to avoid. In some cases, this can be as simple as an excuse. They can also be habits, indulgence in vices or things that just aren’t a good use of your time. Identify them and get rid of them by committing to positive habits.

“If you are depressed you are living in the past, if you are anxious you are living in the future. If you are at peace, you are living in the present.” — Lao Tzu

True presence is peace of mind that comes from knowing you are fully engaged in the moment you’re in. Peace of mind breeds confidence, self-assuredness and clear thought. Isn’t that what we all want? When we’re in that space, we’re fully optimized and actualizing all of our potential.

I think about this in both professional and personal terms, although both are deeply personal to me. I always wanted to do work that helps other people live their best life. Because this is exactly what I’ve wanted for myself. I made it the passion of my life, and thus, the calling for my career.

The true cost of not doing what you love is a life with less enjoyment, happiness, fulfillment and perhaps even, success. It’s honestly a misdirection of your talents and skills.

Find the things you love to do the most and incorporate these into your life. Maybe if you’re lucky enough, they become your career.

Core beliefs, along with values, form our foundation for making smart decisions, building relationships and creating opportunities. They are the key to building a powerful mindset. Beliefs become declarations that we speak over our lives and become a powerful testament to our true self.

There’s an unmistakably magical power of writing and speaking your beliefs over your life. They fuel our psychological and evolutionary growth. Get deep on what you really believe about yourself, about life and about the purpose of what you want to become.

Speaking of purpose, self-worth comes back to your values, purpose and how you live your life. You can start by The Golden Rule: Do unto others as you would like done unto you. By doing good works for others, it washes over us and brings us enjoyment and fulfillment. When we’re doing things in alignment with our values and purpose, we’re living a rich life.

So, go to the source: what do you derive your self-worth from? I’d posit it comes from your character, which is really the aggregate accumulation of the many deposits you make into your figurative piggy bank of good deeds.

“The secret of happiness, you see is not found in seeking more, but in developing the capacity to enjoy less.” — Socrates

Read these incredibly powerful words above. My belief is this is a call to action to get very specific about the things that will enrich our lives. It’s that simple. It’s a call to specificity and minimalism for being our best and experiencing the things life has to offer that are meant for our own enjoyment. Don’t worry about doing more or living someone else’s life. Live yours.

“The greatest blessings of mankind are within us and within our reach. A wise man is content with his lot, whatever it may be, without wishing for what he has not.” — Seneca

This one is very simple. It’s how I begin all of the work I do with my clients:

What do you want?

When you can answer this question rooted in desire, your path will open up to you.

At this point in my life, if I had to answer this question “Yes” or “No” my answer would be, Yes. It’s hardly a binary question, but the truth is, we should care to some degree how others perceive us. Now, before you go ragging on me hear me out on what I believe:

  • I believe we should NOT let the opinions of others hold us back from making decisions or feeling good about ourselves
  • I believe we should NOT let other people dictate our actions or ever reduce our self-worth
  • I believe we should always seek the truth and not let the opinions of others prevent us from living the life we want

That said, the key to successful relationships is empathy. Empathizing with someone is putting ourselves in their shoes. When we can build relationships with empathy, we show that we care. People respect, admire and love when we care about them. And frankly, we should care about comporting ourselves that way.

“No amount of anxiety makes any difference to anything that is going to happen.” — Alan Watts

I believe fear is a compounding effect of subconscious and conscious thoughts that challenge our security and safety and make us feel imperiled or endangered. Fear is an incredibly important emotion and fear can absolutely be real. But it can also be imagined.

The key to an emotionally intelligent life is living with a cognizance and self-management of knowing whether each fear we encounter is real or imagined. So, how we we accomplish this?

We must assess each thought for what it is and analyze it. Is their sensory evidence that it is real? What proof do we have that it is real? Through our self-awareness we can determine how vulnerable or emotional we feel in a given moment to know whether we’re more susceptible to fear.

Write down the way you feel. Speak out loud the way you feel. Through discernment you’ll know whether your belief about your current state is accurate in dealing with real or imagined fear.

Faith is truly belief in what we do not see and certainty toward the hope we have for present and future outcomes. Faith is among the most powerful emotive engines in all of the world. It imbues our thoughts, words and actions and leads to optimism and belief.

I truly believe faith is at the center of living a fulfilled life. You have to believe that your life is going to go in a positive direction. That is so much of a secret toward living with greater perseverance, hope and love.

Learn more about my journey and get great tips on living your best life: http://chrisdconnors.com


Literary Comfort Food for the Soul

Christopher D. Connors

Written by

Author, Executive Coach & Emotional Intelligence Speaker; Seen on Fox, ABC, CNBC, etc.; http://chrisdconnors.com



Authentic, inspirational stories of growth with practical guidance to help you live a happier, successful and more fulfilling life. No fluff. No filter. R3AL.

Christopher D. Connors

Written by

Author, Executive Coach & Emotional Intelligence Speaker; Seen on Fox, ABC, CNBC, etc.; http://chrisdconnors.com



Authentic, inspirational stories of growth with practical guidance to help you live a happier, successful and more fulfilling life. No fluff. No filter. R3AL.

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