The 12 Most Important Questions to Ask Yourself

The 12 Most Important Questions to Ask Yourself

Recently, a friend of mine reminisced about how smooth and easy life had felt when he was in his late teens and early twenties. He used to think he had the right answer to every question. Now, he said, he’s resigned to knowing that he just doesn’t know all that much and misses the old days when the answers were clear. More often than not, I’ve felt the same, and I’m sure you have too. We’re prone to reflecting and wishing we’d known then what we know now. That regret is central to our human essence. There is no way of ever knowing all the mysteries of life. Maybe, instead, we can continue to be guided by the questions.

Humans, like yours truly, have too often focused on thinking we need to have the right answers when, instead, we should focus on asking the right questions.

Questions that have different answers and different meanings at various stages of our lives. Questions that force us to have honest and difficult conversations with ourselves. Questions are windows that can help us truly see when we feel trapped, limited by the constraints of our mind. Breaking through that window can lead us to our greatest potential and fulfillment.

Over the years, I’ve learned to ask myself more and better questions. In today’s blog, I share the 11 questions that have helped me most.

#1 Is This Essential And What If I Said No?

Personal bandwidth has been at the heart of my midlife assessment. Saying yes to things is easy. The harder choice, for me, is knowing when to say no to something. There is no end to the number of Boards we can sit on or charities we can volunteer for. Work is a bottomless pit and social media never turns itself off. Our friends, family, colleagues, and those random people who email or message us on LinkedIn, will always want something from us.

Maybe it’s fear of repercussions that drive us into doing more than we want (or have bandwidth) to do. Maybe keeping busy helps mask our fear of unworthiness or being alone with ourselves. Maybe we’ve bought into the belief that doing more equates to achieving or producing more. Or, maybe we’re just influenced by a time in western culture that idolized those who appear to be insanely productive. As a result, we live in a prosperous and glorious era of money, yes, and burnout, stress, and anxiety.

I’ve stopped buying into this ideal. So, the three questions I ask myself when faced with an opportunity are:

  • Do I have to do this (i.e., is this essential)?

  • Do I want to do this?

  • What would happen if I said “No”?

The hardest to answer is: “What if I said no”? One could deliberate for days or weeks, creating pros and cons charts along the way. Fear of missing out on an opportunity can wreak havoc on our psyche; however, I’ve come to believe that (assuming the answer to the first question is “no”) trusting your intuition will lead you the rest of the way. Saying “no” can just mean saying “no for now” – or it may mean that what you said “no” to is gone forever. Remember, youare allowed to change your mind; what you say “no” to helps shape what you can say “yes” to.

Saying “yes” to something you truly don’t want to do: A) potentially limits your ability to do something else later; B) can cause regrets and an uneasy sense of self-distrust can sink into your bones because you’ve done a disservice to yourself. Deep down it was “you” that told yourself not to do this thing in the first place – and it never feels good not to listen to yourself.

Trust me, saying “no” will become one of the more powerful tools you learn. You won’t really be missing anything. From where I’m standing, after so many years of saying “yes” (and a few of saying no), there are endless things to say “yes” to. So, wait for what feels right. Some tips and ideas to help frame the “no” decision:

  • Would I travel to a place if it wasn’t a vacation?

  • Would I have dinner with this/these business associate(s) outside of work?

  • Would I take on this project if I didn’t have to?

  • Would I buy this thing if my neighbor or colleague hadn’t recommended it?

Your time is the most valuable asset you have. The way you spend your time directly correlates with your mental health. If you practice giving out more “no’s”  you’ll eventually settle into the pure joy and clarity that comes from doing less.

 #2 What if I Just Held the Cat?

Sometimes when I’m working from home, our family cat will slowly but surely make its way over to my lap. I can see her coming a mile away! Eventually, she plops herself strategically between me and my laptop – making typing a near impossibility.

Now, I almost always pause what I’m doing just to hold the cat.

We should ask ourselves this question: “What if I just did nothing instead of taking action?” This is akin to saying “No.” Always the one to push through, I’ve routinely found myself stressing over decisions, working myself to exhaustion, and feeling a general sense of congestion or overwhelm. This results in, among other things, me making mountains out of molehills and sending emails I should have waited a day to send (or not sent at all). MOST things are only molehills, and we can see that when we just take a moment to pause and hold the cat!

“It takes practice to willingly miss out on all the possibilities. But if you take steps to recondition yourself – and withdraw from these demands to consume and change – there is a lot of pleasure that can be derived from disengagement. It can open you up for deeper connections to the world and deeper relationships to other people, and ultimately, bring you more joy.”

Dr. Brinkmann

 #3 What Am I Willing to Struggle For?

This question is a carryover from the first question. Generally speaking, nothing is really as easy as it may appear on the surface. To achieve success, happiness, physical fitness, and healthy, thriving relationships requires struggle. Let’s be clear, I’m specifically choosing the word struggle and not suffer as there is a world of difference between the two. Suffering usually means what we’re doing isn’t right for us and it’s time for a change while struggling implies that there is resistance, but that resistance positively shapes us…not hurts us. We can struggle elegantly, gracefully, and with reverence.

So why does happiness have to be “struggled” for? Because, for a great many of us, happiness usually comes with the difficult committed work of letting go of expectations, fears, limiting beliefs, and concepts and becoming aware of who we are deep down inside. That journey can take a lifetime.

If you want to be a successful person, either as an entrepreneur or by climbing the corporate ladder’s long work weeks, risk and sacrifice are part and parcel.

Successful relationships are born of time spent listening, working through differences of opinion, finding balance, releasing past pains and, often, choosing to keep this relationship over and over again.

Those who meditate and spend years in spiritual practice and contemplative reflection, battling their demons and egos along the way, are usually the ones who achieve self-actualization and freedom from suffering.

Those who spend the most time pushing themselves physically by lifting weights or running or swimming or climbing giant rock faces are the fittest.

As Henry David Thoreau said, “The price of anything is the amount of life you exchange for it.” If it turns out you’re not willing to struggle for the thing you wanted, you don’t really want it. Move on.

I think you get the idea. The point is, struggle is a basic component of our lives, and part of determining our success. And, by nature, struggle comes with great sacrifice. So what are you willing to struggle for?


#4 Why Am I Doing This?

Does the spirit move you? Why?

This question is often overlooked yet correlates with the first two: “Why am I doing this? Do I love this thing (be it a job, a relationship, a place you live) or do I love what it provides me? Is this something I would do if I had the choice not to? Is the reason I’m doing it satisfactory to my soul? The trap we must try to avoid is doing things because they have become a habit, an obligation, or because we think we have a choice: someone told us it was required or the right thing to do.

Once a day, once a week, or once a year…whichever suits you, take the time to pause and ask yourself why you are doing something. Dig deep and uncover the real reason behind it. Why am I building this business? Why am I dating this person? Why am I spending time with these people? Why do I have this hobby? Why do I put my kids in so many activities?

Asking this question isn’t about overcomplicating the decisions we’ve already made tough enough. This is the simplest question we often have the hardest time asking and answering… “Why am I doing this?” A related question could be, “Why am I doing it this way.” There could be an easier or more efficient, productive or rewarding way of doing the same thing. What about the question, “What if I did the thing I wanted to do?” How often are we guilty of delaying or postponing the things we want to do (the things that give us the best answer to our WHY) until much later in our lives.

“I’ll do that (what I really want to do) when…” is an all too common refrain. This doesn’t just have to be a dream vacation either, this can be starting a business or leaving a business. As I said above, we can certainly find the love in what we do. It’s just important to ensure that love (aka our WHY) is still there.

A man who does not have something for which he is willing to die is not fit to live.”
Martin Luther King Jr.

#5 Is It Kind, Necessary, Or True?

Look no further than the beloved internet to see that our precious world is a wasteland of words that are unkind, unnecessary and untrue. This is why the questions I ask my daughters are the same simple questions I ask myself before I say or do anything.

Is it kind? I try to fill people’s buckets with loving kindness, not tear them down. Brutal honesty is sometimes required, but more often than not, kindness is the way to serve it up. Our world is filled with enough things to make us feel pretty shitty about ourselves, so be the one person that spreads the love.

Is it necessary? Aside from the occasional bullshitting session with your mates, we still tend to say too much (and listen too little). We learn a helluva lot more from listening than talking and, often, most of what we say doesn’t really move us – spiritually, mentally or intellectually – in a better direction; take it from someone who talks too much! So, before you share, ask: Is this necessary? It may be VERY necessary but maybe it’s something best left unsaid, or at least said after further consideration.

Is it true? 1)You shouldn’t tell lies (not even to yourself) and, 2) Your truth deserves to be shared – particularly if it hits both kind and necessary.

But let’s face it, the world is filled with lies (or at least filtered,  photoshopped, curated , contradictory and highly subjective truths). So, be a speaker of truth.

For all three, ask yourself, “Could I look myself in the mirror and say that what I just did or said was genuinely kind, necessary and true?”

The mind, once stretched by a new idea, never returns to its original dimensions.”― Ralph Waldo Emerson

#6 What If All The Concepts I Believe Aren’t True?

 From birth onwards, our beautiful mind is jam-packed full of concepts. Concepts we learned from TV shows and advertising; concepts our parents taught us about right and wrong, and how to live our lives; cultural concepts about how much to work or what are the right jobs to do; concepts about relationships, gender and sexual identification; concepts about political views, money, and … literally EVERYTHING.

But what if they aren’t true?

Our concepts become the first filter from which we perceive the world and thus make most of our decisions. Whether we do something or not is likely driven by our concept of the thing. This can certainly provide structure and organization to our decision-making process and life choices. But then there are the moments and decisions that just don’t “feel right.” Sure, we think we know what should do (or at least what our parents, professors, or other favorite influencers have directly or indirectly suggested we should do) in any given situation, but what if our guts are churning and we just want to go a different way? Our OWN way!

This is the time to ask ourselves: Are our concepts A) Actually true (which they are not because they only represent one aspect of a potentially infinite number of truths); B) Are they true for me?; C) If they are no longer true for, me what should I do?

The answers, I’m sure you will find, will always help align you with who you truly are and where you are, and set you free on the road to the life YOU are meant to live.

That’s not to say, however, that it will be easy. Which leads to the next question:

#7 What Is The Worst Thing That Can Happen And Am I Okay With That?

This life question dating, back to somewhere between 121 CE and 180 CE, comes to us from the great philosopher and leader, Marcus Aurelius.

It is a simple, yet powerful, question with a related practice that helps us make key decisions. Answering the question truthfully for ourselves removes anxiety about the great unknown future. If we CAN be okay with the worst-case scenario, then what is there to worry about? If we can’t, then maybe we should re-think our next action.

This teaching, and many other stoic philosophy teachings, remain as relevant today. They can be found in Meditationsby Marc Aurelius and The Obstacle is the Way by Ryan Holiday.

#8 What Would I Think About This Twenty Years From Now? 

Once, while deep in a guided meditation to meet a spirit guide, I was genuinely surprised to meet my future self. Happy, content, radiant, calm – all the things I wasn’t feeling at the time. Yet, there I was living my best life in the spirit realm. Casting aside the “spirit realmness” of my example, why did I later realize that meeting my future self and having him as a teacher made so much damn sense? Because he knows me best!

Digressing for a moment back to point number 5, we experience the world through the concepts we’ve been taught. As I said, these concepts, bred from the modern consumer culture and pressures of marketers and people of influence, taint our present thinking with clouds of confusion, guilt, shame, and doubt. They create false concepts that make it seem impossible to reconcile the answers to our own questions. Often framing these questions to a spiritual deity in the form of “why” or “what” should I do, we quietly and anxiously wallow in a feeling of helplessness. Yet, deep down, the answer is already present inside of us. Posing the question to yourself, 20 years from now, detaches your current ego and helps you see the answer inside. Think about it this way, if we ask ourselves the question: “Should I be spending more time with my children or working…because there is so much work to do?” What do you think your future self would say?

When sinking in worry about a bill or being fired, do you think your future self would say, “Relax… It will all work out. You don’t have to get caught up worrying about every little thing.”

Or, when you ask yourself “Why am I doing this” (question 3)…or, am I, as Joseph Campbell said, “following my bliss,” who is the best person to ask for guidance? YOU – twenty years from now. Because seeing yourself, living your “Why,” living in peace, helps you to believe that the thing IS possible. You are your own beacon to becoming your best self.

Lastly, this practice, if done regularly, helps you learn to trust and connect with yourself.

#9 What Am I Grateful For And What Can I Be Proud Of?

Small wins, big wins, they’re all the same! To create positive momentum, happiness, and a true appreciation for the gift that is your life, think about what you can be grateful for and proud of every single day. Make reciting, recording, re-visiting, re-feeling and remembering your “What am I grateful for?” the one habit that rules them all.


#10 What Would I Bring If I Was Trapped On A Deserted Island?

This question isn’t actually about the five “things” you’d take if you had to go live on a deserted island. Although that question certainly provides a valuable exercise in what you truly need and/or cherish, this question is about the desires you would take. Now, scrap the island metaphor as this one desire you actually get for your real life. But choose wisely because as Naval Ravikant says, “Desire is a contract you make with yourself to be unhappy until you get what you want.” The ever insightful Naval continues by remining us to “ keep that in front of mind… Pick your one overwhelming desire. It’s okay to suffer over that one. The universe is rigged in such a way that if you just want one thing and you focus on that, you will get it. But everything else, you gotta let go.”

There will be a lot of things in your life that you desire to do, see, accomplish, and overcome, but what if it were just one – what would that be?


#11 What Do I Need To Know Right Now?

Usually, of all the things spinning around in our minds, there is only one single thing we need to figure out or understand at any moment. This may be a big thing or it could be a little thing. In our company, we call this blocking and tackling. But I’ve come to think about this in a larger way. Maybe the thing I need to know is something I had to learn. For example, maybe it’s just figuring out effectively how to send a mass email blast or maybe its needing to learn computer programming because that is where the opportunity is. Maybe we need to know Spanish because we’re about to spend a year in Spain. Maybe we need to know how to forgive ourselves or how to be more compassionate. Maybe it’s truly learning and better understanding a current moment in time – such as #metoo or #blacklivesmatter or who to vote for in a presidential election. Usually, it’s just one thing that, when known, moves us forward. Once we know it, then the question will present itself again, and again, and again. By homing in on the one thing we need to know to achieve we can achieve anything we want in this life one thoughtful and powerful step at a time.


#12 What if I could live this day again?

This is one of my favorite questions! For whatever reason, I really, really liked the movie, “About Time.” I guess it made me think about my father and cherishing the time I have left with him. The men in the fictional family can time travel. At one particular point, the father advises his young son to go back and live the same day over again. He wanted him to notice how different it feels when you experience all the stresses and worries for the second time; in effect, they go away and we are left with the gift of the realization that each moment is precious.

It reminds me of two quotes:

Every person has two lives, and the second starts when they realize they have just one.


Live as if you were living a second time, and as though you had acted wrongly the first time.
Viktor Frankl

This question is connected to question #8: What would we say 20 years from now? In other words, when it comes to the events of our day, how would we “do it” and “feel it” again, knowing what we know now? So, for all outbursts, fear-based thinking, stress, and rushing that we left in our wake – the following morning may bring the hangover of awareness of “why did I do it that way when I could have ___________ (you fill in the blank).”

Memento mori (Latin for remember death) is another way of posing this question to ourselves. If I knew I were to die tomorrow, how would I live this last day? So naturally, we can practice this two ways: First, we can contemplate this in the morning, cultivating the idea that tomorrow may never come and thus we should act, presently, full of love and free of worry; and two, as reflection on the day, we just had and how we may have done things differently.

 In this sense, hindsight does not need to be 20/20. Because we take the learning of our personal history forward into every moment and, with new awareness, live each day as if we had got to do it again.

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