On Living Authentically: Part II

Click here if you missed Part I

I left you hanging last time, sorry, but it was for the better, I think. You get more time to absorb the last post and I get more time to draft this one. Win-win.

I’ve already cleared up what my version of living authentically is, and why it’s important to live authentically, true, but so where do we go from here? What’s next? Armchair philosophizing is fun, but even better if I can inspire at least one person reading this to stop what they’re doing, rethink the direction of their life, and transform into a better version of themselves.

I’m looking to uncover the subtle influence of creeping normality that has gradually picked away little chunks of your soul, year by year, little by little, forcing you to give up the things you truly love in life in favour of what’s ‘easy’ ‘safe’ or ‘conservative’. So stop neglecting about those dormant goals left idling in the backburner of your brain, take my guidebook, and walk with me on the path of self-improvement.


Let’s get started

Now that we’re fresh again, I’ll begin by asking you a simple question. This is important: note what comes up into the chamber of your thoughts right away. Don’t rationalize, don’t second guess, just allow whatever comes up to surface freely. Write it down immediately. Yes, on that scrap piece of paper laying in the corner of your desk. Please don’t make it into a mental exercise, allow your intuition to guide you. Alright? Let’s do it.

Ask yourself, as in right at this very moment, with absolutely sincerity: “am I living an authentic life?”


It’s a tough question to answer, right? Good, it should be, it means you’re taking this seriously enough.

I can’t answer this question for you. If I did, I’d be imposing my ideals and values on your life. My attempt to persuade you on how to live your life–detailing what my version of authenticity is, and undoubtedly, not yours–goes against the very basic tenant of authentic living. Because the only person who can answer the “am I living an authentic life” question is you. That’s the beautiful and challenging thing about today’s theme; there is not one universally correct definition of what an authentic life is, and the answer can and does vary wildly for each person.

The huge variance and inconsistency in the possible spectrum of answers to the previous question is a little intimidating. Why? We’re obsessed with absolutes and certainties in society, always attempting to quantify the incalculable and objectify the mysterious. Sorry to say, there’s no mathematical formula here. No fundamental answer to the ultimate question of life, the universe and everything. You must be the one to invent your own meaning, your own purpose, and it is you who must act on it. All I can offer is some lubricant for the turning gears in your head. I’ll buy you a swimsuit, friend, but you’re the one who has to take the plunge.



The previous question was only a warm-up, something to get the wheels turning. If you felt the previous question was too generic (it was), and your answer all over the place (it should be), rest assured that what follows will make more sense.

I’ll ask you a puzzling array of open ended questions, broken up in 5 convenient categories. It’s up to you to answer them honestly and critically. Take the time to think about each one, spending less or more time on each question, depending on what feels right. These are simple questions, yet, taken together, they have profound implications. We’re looking for that visceral gut reaction, that odd confusing epiphany, that unexplainable whirlwind of emotions… not reasoned justifications from the rational part of your brain.


There’s only 1 rule.

Be as sincere as possible. That means, I want you to ignore all the comforting filters that make uncomfortable questions easy. Rip off the blindfold your ego has tightly nursed around your precious psyche. Body slam that aura of complacence that’s so often convinced you to take the road more travelled. Take out your wire cutters, and liberate yourself from the fishing net of doubt you’ve cast over yourself your entire life. Get your shovel ready (or jackhammer, if you please) and dig down deep with me into the unexplored crevices of your deepest darkest corners of your mind.



5 Pillars of Authentic Living


  • Do you feel like you truly know who you are?
  • Do you struggle with matters of personal identity?
  • What greatly frustrates you about yourself? What are you doing about it?
  • What human qualities do you deeply value in others? In a partner? In a significant other? In family? Are you acting in alignment with them?
  • What qualities make your best friend(s) your closest allies?
  • Do you make yourself vulnerable to others (thanks Carla)?
  • Do you have a mentor or role model in your life, someone to aspire to?



  • Do you feel you fit in a preconceived label/box within society?
  • Do you share your values with a majority opinion?
  • Do you derive a sense of community within the neighbourhood or district you’re living in?
  • Are you content with the direction your country is steering towards?
  • Do you benefit from or are handicapped by the dominant culture in your city/country?
  • Do you revel in or suffer from the community/religion/culture you were born into?
  • Are there social stigmas that you live in defiance of?
  • What ‘big’ causes do you truly identify with?



  • Do you feel “stuck” or “in a rut”?
  • Have you ever considered alternative ways of living day-to-day?
  • From the second you wake up to the minute you pass out at night, are happy with your daily schedule?
  • How many times this past month did you dread waking up in the morning (hangovers and Mondays excluded)?
  • Do you feel like you’re living to impress other people? To keep up with appearances?
  • What do you spend the majority of your disposable income on? Do you prefer buy goods or experiences?
  • What’s the minimum amount of material possessions you need to feel ‘comfortable’?
  • Are there situations or certain groups of people where you feel the need to behave differently, not being 100% yourself? How often?



  • Do you feel your job defines an integral part of you who are, or is it merely an extrinsic activity to support yourself?
  • Are you a completely different person, an “actor,” at your workplace?
  • Are you expendable? Do you feel you hold a bullshit job, being a hapless cog in a ruthless machine, or are your efforts noticeable, appreciated or integral?
  • Are you doing what you always wanted to be doing? What did you want to be when you were a child?
  • Does your job bring you fulfilment in some form or another?
  • What external pressures are holding you back from achieving your ideal career? Family? Friends? A significant other? Debt? Health?
  • What internal pressures are holding you back from achieving your ideal career? Self-confidence? Motivation? Fear of change? Fear of failure?



  • Where do you see yourself in 10 years? This is a timeless interview question, but ignore your career for a second and answer it in the context of the other areas of your life.
  • What kind of activities give you the greatest sense of purpose?
  • From what do you derive meaning? What drives your will to continue living?
  • What are you passionate about?
  • Does the future appear bleak and uneventful? What are you doing about it?
  • Or full of possibilities and potential? What are you doing to make sure it plays out that way?
  • What motivates you? Money? Altruism? Family? Stability? Leaving a legacy? All are perfectly valid, but are you sure you know what you want?


What to do about it all

Phew. A lot to digest, right? Truthfully, I don’t yet know the answer to some of these myself. And let’s be honest here, it’s damn near impossible to. I designed the questions to be stimulating, get you thinking, and channel your thoughts to ‘big picture’ ideas. My list of questions is by no means exhaustive, and by no means is every question applicable to the entirety of the human race, but it’s a start.

If any of the questions made you feel uneasy, uncomfortable or puzzled, good. That’s exactly what we’re looking for. There are deep-rooted reasons for explaining why you feel the way you feel, and the longer and more frequently you practice introspection, steered by questions like the ones above, the more acquainted you’ll begin to feel with your true self.

If you’re serious about living more authentically, I recommend writing down your answers to the list of questions above, and make these answers as accessible as possible in your daily life. Or create your very own ‘pillars of authentic living’, with personalized thought-provoking questions that you feel are more relevant to you.

Print your answers out. Sharpie them on a bathroom stall. Add them into your favourite mobile ‘list’ app. Make sticky notes on your fridge. Tattoo them on your ribs. Read them on the subway. Glue them on the wall beside your bed so it’s the first thing you see when you wake up in the morning. Or, better yet, create an authenticity journal that logs your progress in answering these questions. Whatever you have to do, do it. Refer back to your list with diligent regularity, eventually so the answers are permanently etched in your brain. Everyone is different, so I won’t suggest an ideal method here, but the most important thing is to act, in one form or another.

Make it a daily goal to do one tiny thing, no matter how seemingly insignificant, that is in accordance with your answers. Buy a fruit from a local food vendor. Spend 20 minutes researching alternate careers paths. Book a plane ticket for a weekend getaway. Message an old friend. Invest into a new pair of running shoes. Meditate. Think about what truly makes you happy. Take half an hour to carve out your deepest desires and formulate a rudimentary definition of your meaning of life. Then write it all down. Then revisit it a month later, adding or subtracting to it as you see fit. Most importantly, don’t get stuck overthinking, make sure to actually act on your answers. We often get sidetracked, as I do, in romanticized bubbles of thoughts, yet forget to actually materialize anything we daydream about. Intentions are nothing without action.

Moving forward, you have two possible paths to venture on: the bumpy, unpredictable hill of authentic living or the smoothly cemented pathway of ordinary life. You’re in the driver’s seat of adulthood now, and the rest of your life will unfold in accordance with which path you decide to take. Choose wisely.



I hope I got the ball rolling here and challenged you to look inwards, if only for a brief moment. Coming to grips with the fact that you’re living an inauthentic life is one of the hardest things you can do for yourself—yet one of the most rewarding. Most of my readers are about my age, 24, give or take, so heed this warning: Our brain becomes significantly less plastic after the age of 25, making dramatic changes to your behaviour or personality , and consequently, life, that much more difficult. This explains why most older people (though not all!) tend to be more conservative and safe.

While your precious dome is still malleable, while you’re still beaming with vitality and energy, before you lock down a permanent seat in the weekly Bridge game, and before life’s inevitable chains drag you down and solidify your place in this universe, DO SOMETHING. ACT. CHANGE. LIVE. Take risks, and reap their consequences. Learn from your mistakes, and evolve from your triumphs. Live a more authentic life!

Trust me, you have the capacity to change. Challenge the invisible paradigms that have compelled you to sacrifice the things you deeply treasure. Subvert those malicious thoughts that you’re too conservative, too unskilled, too timid, to change.  Smash your self-doubt into infinitesimal pieces. Take pride in your abilities, realize your potential, and bring your dreams into sweet fruition. Believe in yourself. It doesn’t matter if no one else does, I do.



Did all this make sense? Only some of it? Did I hit a sensitive nerve? Or am I just a big fat stupid doodoo head? All perfectly valid responses. Be bold! Let me know! I’d like to hear from you, and I mean it. Do you feel like you’re living an authentic life? Do you feel you aren’t? I’m here to guide you through one of life’s most difficult mazes, the labyrinth of authenticity. I don’t quite have it figured for myself, nor do I claim to, but having a helping hand or someone willing to listen is always useful.

I challenge you to ask yourself the questions that I laid out above. Remember, there’s no correct answer, this is entirely subjective. Take as long as you need. Just so you know, I hold an open door policy for discussing anything I publish on this blog, so message me if you want to bounce some idea off me.I hope you enjoyed your (brief) journey of self-exploration with me.

Take care, and in the words of a good friend of mine, ‘be real.’





After doing some extra homework on the topic, it turns out in existential philosophy writers like Sartre already beat me to the punch. We talk about essentially the same thing, but in different words. Sartre, in particular, describes a lack of ‘authenticity’ as bad faith, with some lucid examples on this wikipedia page to help explain what he’s talking about. Have a look if you’re interested in diving deeper about this topic.



Believe me, before, and especially, during, writing this post, I realized how fortunate I was to be wearing the proverbial shoes I am wearing today. I benefit daily from a host of privileges—‘advantages’ that I’ve been gifted with through my completely random birth in this world—that have allowed, and continue to allow me, to take on new challenges, experiment with novel thoughts or ideas, and undergo new experiences . I profit regularly from the benefits of my linguistic privilege of speaking English, allowing me to move abroad and find work super quickly as an English teacher, though I never formally studied the language in any capacity. As a native English speaker, the world is my oyster. I can spontaneously pick a multitude of countries in the world that would accept me with open arms.

I was fortunate to be born into a caring and supportive family that helped fund my tuition fees, raised in a democratic country where I could pursue any individualistic whim that I so desire, and haven’t faced racism or oppression due to indelible attributes one is born with, like gender, disabilities or race. I don’t have to fear the repercussions of acting in wild defiance of a repressive culture I was born into. I don’t have any social stigmas to overcome or biases to defend. I have a roof over my head, food to eat, water to drink, good health, and a bed to sleep on, all of which are essential needs before one can even begin to entertain the idea of authenticity.

For all this I am eternally grateful.


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