Thought Provoking Questions About Life and Work

There’s always another level, and good questions can help you get there.

How do you get to the next level in life? It’s a question that makes you think. Sadly, not many people bother to ask thought provoking questions.

The only way to get better at anything is to ask better questions. No one knows what they’re doing. Everyone from your parents, teachers, scientists to politicians and ultra-successful are just trying to figure it out.

Before “Game of Thrones” and Jon Snow, who knew nothing, there was Socrates, who’s known for knowing nothing, “I am the wisest man alive, for I know one thing, and that is that I know nothing.”

Only by detaching yourself from the ego and embracing the unknown you can learn. Nobel Prize winner and world-renowned physicist Richard Feynman summarizes it perfectly:

I think that when we know that we actually do live in uncertainty, then we ought to admit it; it is of great value to realize that we do not know the answers to different questions. This attitude of mind – this attitude of uncertainty – is vital to the scientist, and it is this attitude of mind which the student must first acquire.

Over the years, curiosity led me to unexpected places, interesting people, life-changing books and some powerful thought provoking questions.

Here’s my collection of questions that make you think about life and how to get to the next level.

There’s always another level.

Thought Provoking Questions

Gary Keller, the author of The One Thing, claims that great questions are clearly the quickest path to great answers.

Voltaire once wrote, “Judge a man by his questions rather than his answers.” Sir Francis Bacon added, “A prudent question is one-half of wisdom.”

Indira Gandhi concluded that “the power to question is the basis of all human progress.”

What Is the Source of Your Unhappiness?

This powerful question comes from one of the most influential self-help books, Think and Grow Rich by Napoleon Hill.

What connection, if any, do you see between the people with whom you associate most closely, and any unhappiness you may experience?

Sometimes you have to make the hard decision and cut people off. Trust me, it will be better for both parties.

What’s the ONE thing I can do, such that by doing it everything else will become easier or unnecessary?

It's counterintuitive but maybe that's why this question by Gary Keller is so powerful.

Why Worry About Anything Else Than Now?

Practicing meditation is one of the most rewarding experiences in my life. The Power of Now by Eckhart Tolle completely shattered my perspective on life and offered practical frameworks to cope with the reality as it is.

Ask yourself what “problem” you have right now, not next year, tomorrow, or five minutes from now. What is wrong with this moment? You can always cope with the Now, but you can never cope with the future — nor do you have to.

Cultivating a habit of constantly asking yourself how do you feel right now can radically transform how you cope with the problems, that mostly exist in your mind and never materialize.

Who Do You Compare Yourself To?

The following question comes from Ego Is the Enemy by Ryan Holiday which offers an array of stories illustrating how throughout the history ego ruined lives, families, nations, and empires.

The question we must ask for ourselves is: Are we going to be miserable just because other people are?

Comparison is your number one enemy and the main reason humans are so unhappy and lost.

What’s the Proper Way to Pray?

One of my readers, Thomas Haladner, an Analytical Psychologist shared the following question that makes me think about my attitude.

What is the proper way to pray i.e. does one pray for a better outcome or a better attitude and how does one find and stay on one’s true path?

There’s so much in life you can’t control but you still need to figure out how to navigate through life without a map. I bet on praying for a better attitude and resilience to bounce back from the inevitable hardships.

Is This a Good Idea?

How do you know if your idea is a good idea? Put it to a test, before you even lift a finger. This powerful thought experiment comes from Justin Jackson.

First, ask yourself:

Who is it for?
What is it for?

Put another way:

What group of people am I making this for?
How will they use it to make their lives better? What superpower does it give them? (And how is it better than what they’re already using?)

These questions will give you clues as to whether your idea is worth pursuing.

What Would the World Be Like Without Me?

This simple exercise comes from Chris Bailey. Keep it in mind as you consider what to accomplish next year, and where you want to spend your time, attention, and energy:

Imagine two worlds.

The first world has you in it.

The second world doesn’t.

What is the difference between these two worlds?

Is This for Me?

The other day, one of my readers, Bruce Layman shared a provoking question that makes the decision-making process easier. Simply ask yourself “Is this (book, movie, TV show, podcast, band, etc.) for me?”

If not, it’s okay. Let other people enjoy it and continue consuming the things that surprise and delight you.

Here’s how Bruce explains it:

It keeps you from being a karma suck about things that people like. I didn’t watch a single episode of Game of Thrones (gasp, I know!) and when people would ask me, “Why don’t you watch the show, it’s the BEST SHOW EVAAAARRRRR!” I could respond that it simply wasn’t for me. I didn’t have to say anything negative about it, not even that I didn’t like it, only that it isn’t for me.

I like how using this approach allows you to say “no” in such a powerful and neutral way.

Do You Idolize Your Heroes?

It’s easy to think of your heroes as extraordinary people. But quite often you only see a small piece of the big picture. The following question comes from one of my favorite books, Mindset by Carol Dweck.

Think about your hero. Do you think of this person as someone with extraordinary abilities who achieved with little effort?

Now go find out the truth. Find out the tremendous effort that went into their accomplishment—and admire them more.

How Do You Learn?

“To know thyself is the beginning of wisdom,” wrote Socrates. Knowing yourself is within your circle of influence. The following questions come from a little yet profound management book, Managing Oneself by Peter F. Drucker.

Am I a reader or a listener? and How do I learn? are the first questions to ask.

But they are by no means the only ones. To manage yourself effectively, you also have to ask, Do I work well with people, or am I a loner? And if you do work well with people, you then must ask, In what relationship?

What Do You Do in the Morning?

Many people struggle to get up in the morning. My theory is that most people lack the purpose in life. It’s hard to get excited about waking up early when all you can think of is how to survive the day and get back to bed.

The following thought provoking question comes from a changing book, The Miracle Morning by Hal Elrod.

Why did you bother getting out of bed this morning? Think about that for a second…

The old saying, “you snooze, you lose” may have a much deeper meaning than any of us realized. Your entire life changes the day that you decide you will no longer accept mediocrity for yourself.

Are We All Not Just Two Minutes From the Abyss Anyway?

The following questions come from a short book, Two Minutes from the Abyss by Vijay Eswaran.

Do we realize how close we all are from the abyss at any time? Do we even acknowledge it? Do we live our lives in a manner respectful of that understanding?

Every day, I try to remind myself that I’ll die. Tomorrow isn’t promised to anyone.

While it may sound negative, it’s an ancient practice gaining popularity among modern Stoicism followers. Memento mori is the medieval theory and practice of reflection on mortality, especially as a means of considering the vanity of earthly life and the transient nature of all earthly goods and pursuits.

Better Questions, Better Life

I hope you found an interesting question that made you think. Make it a habit to ask better questions.

While asking better questions isn’t easy, pondering on thought provoking questions can help you live a more intentional and fulfilling life.