Unmasking My Shadow

Most people hate long haul flights. I love them. Why? Because until the wifi gets good enough, which I hope it never does, long haul flights are one of the last vestiges of disconnection from the world. While we can indeed partake in a digital detox at ground zero, having no choice but to disconnect while giving those on the outside no way to contact us, is liberating, and allows us to engage in guilt-free ‘me time’. Not only do long haul flights give us an opportunity to disconnect from the world, but more importantly, an opportunity to reconnect with ourselves.

My long-haul ‘me time’ consists of reading, listening to a podcast episode or two, watching a movie, stretching, walking up and down the flight of stairs at the rear of an A380, and perhaps most importantly, taking time to reflect on my personal and professional life (usually over a glass of Shiraz, cheese, crackers and the somewhat questionable salami sticks — a simple guilty pleasure of mine).

The Mask and the Shadow

On a recent flight from Melbourne en route to Bangkok for the Innov8rs Conference, I was reading author Robert Greene’s new magnum opus, Laws of Human Nature. I had the honor of speaking with Greene on my podcast Future Squared recently and was struck by something he said during our conversation about the notion of masks and shadows. Greene says that each of us wears a mask in order to gain social acceptance. This mask hides our dark side, or, our shadow, which can be a true but suppressed representation of our personalities.

“People tend to wear the mask that shows them off in the best possible light — humble, confident, diligent. They learn to conceal their insecurities and envy. Fortunately, the mask has cracks in it.”

The concept of the shadow comes from psychiatrist and psychoanalyst, Carl Jung, and refers to ‘the unconscious aspect of the personality which the conscious ego doesn’t identify in itself’. Someone’s shadow is prone to making an appearance under conditions of high stress, intoxication, when triggered by an external event, when underslept or fatigued, when willpower is depleted (often late at night), or in the dream state.

As a result of suppressing our shadow, as adults, we have a proclivity to become boring, unadventurous, devoid of play and creativity, and wind up seeking a reprieve for the suppressed part of our personalities through sex, drugs, and voyeurism. Greene says that various Machiavellian characters enthrall us and that we lap up news of those who have been caught acting out in some way because it helps us release our own tension.

By becoming aware of our deepest secrets, we can master our natures.

Unmasking Shadows

Greene put forward a number of signals in the book to help decode both your own and other people’s shadows, including the following:

  • Contradictory behavior: actions that belie the carefully constructed front people present
  • Emotional outbursts: suddenly losing one’s habitual self-control and saying something biting and hurtful
  • Over-idealization: charged with emotional conviction and glossing over the faults of our cause, seeing things only in black and white (see moral righteousness and activism)
  • Projection: we can’t admit to ourselves certain desires (eg. for money, sex or fame) so we project those desires onto others (“he’s so self-important”)
  • The Tough Guy: rough masculinity concealing emotional vulnerability and tenderness
  • Passive Aggressive Charmer: amazingly nice and accommodating, with a tendency to smile a lot to get what they want, and likely to stab you in the back later on
  • Snob: a tremendous need to be different and assert superiority
Like, Spotify is beneath me.

I invested a couple of hours on this particular flight towards getting to know myself better. Of course, I don’t think that two hours or personal reflection is enough to truly understand my deepest, darkest drivers, but it is on the back of ongoing introspection which makes it easier, and if nothing else, it’s a lot more than what most people invest in getting to understand themselves better.

So why not just keep this to myself?

Showing vulnerability is something I am comfortable doing. We all have our shadows. We are all a byproduct of biological evolution, genetics, upbringing, past experience, social conditioning, and our immediate environments. If we can all be a little more authentic and vulnerable, we can get to know each other’s true self better and have more rewarding personal relationships. We can accept people for who they truly are, rather than the people that society would have them be.

Contradictory Behaviour

Over the years, some might say I’ve built an identity around discipline. Whether that be the early rising, the daily workouts, or the focus and energy I put into my entrepreneurial ventures. I also try to maintain a stoic demeanor and be deliberately responsive when things go wrong, rather than emotionally reactive, as much as my limited free will allows.

However, I sometimes catch myself doing the following:

  • binging on junk food
  • taking the path of least resistance, purely to avoid confrontation and friction
  • seeking instant gratification at the peril of the future
  • wasting time responding to pointless emails and surfing social media
  • being impatient with people and external circumstances, and losing my sh*t as a result
  • opting for an easy workout in the gym instead of pushing myself
  • saying hurtful things or balking at external circumstances not going my way

Emotional Outbursts

Despite my best intentions to subscribe to the Stoic school of philosophy laid down by thinkers such as Epictetus and Seneca two millennia ago, I occasionally lose my cool. More often than not, it’s at those closest to me — family members, colleagues, friends, lovers.

When I reflect on what triggers these outbursts, it tends to be around my aversion to enmeshment or having my freedom diminished, a perceived lack of control, and impatience for what I see as irrational or childish behavior.


In today’s divisive world, many are using ideals and causes to fast-track their own moral righteousness (see social justice warriors and alt-right skinheads). This is usually tied to one’s need for identity and community.

In my case, I have a tendency to over-idealize attributes that form a large part of my own identity, such as freedom and autonomy, the free exchange of ideas, fitness and mental wellbeing, productivity, emotional awareness, learning, eating well, discipline, embracing adversity and hard work, taking ownership, and so on.


Oftentimes, what we hate about or judge in other people is a reflection of something we wish we had ourselves or something we may ourselves be suppressing.

I project onto others self-absorption, greed, poor emotional intelligence, bad manners (such as speaking loudly on the phone in public places), over-assertiveness, and laziness. Perhaps these are all things that I either see in myself or wish I possessed more of? Perhaps I wish I was more assertive or didn’t care what people thought about me when I spoke on the phone whilst on the train? Perhaps I wish I could be a little lazier without berating myself or hurting my self-esteem? Perhaps my disdain for people who are driven purely by dollars is a reflection of my being driven by the same or a justification of my own world view where one should put purpose before profit?

The Tough Guy

Whilst I like to project discipline and confidence, I like many others who may not care to admit it, am ultimately not averse to crying at the silliest of things (this includes Pixar movies such as Up!). I can be quite sentimental which makes it hard for me to part with things or people, and can often feel melancholy and succumb to moments of weakness.

The Passive Aggressive Charmer

I’d be lying if I said I’ve never said just the right things, and smiled in just the right way, and used just the right body language, in order to either attract women or secure business deals, only for my demeanor and attitude to change shortly thereafter.

The Snob

This is one aspect of my character I’ve been working hard to change for the past couple of years, engaging in exercises like ’21 days of no judging’, and other mindfulness exercises. I have a long history of consciously or otherwise thumbing my nose at people for being simpletons, for being drawn to trashy pop-culture media, for being overweight, for having a nonchalant attitude towards life, for not working out, for using their smartphones too much, for having no clear direction in life or simply, for poor dress sense.


Greene also urges readers to reflect on their childhood and young adulthood and look for traits and behaviors that defined who we were that we may have since suppressed in order to show up in the world in the most positive light possible. As a teen and twenty-something, I was adventurous, rebellious, competitive, partied — a lot — and did my fair share of what some might call, womanizing.

Learnings and Action Steps

Having synthesized the above reflections, my shadow is perhaps best characterized by insecurity, authoritarianism, judgmentalism, self-absorption, ego gratification, spontaneity, alcoholism, irrationality, envy, fear, and deception.

By becoming more aware of my shadow traits, I can:

  • More readily recognize my shadow when it appears and put the brakes on any negative tendencies such as emotional outbursts and saying things I’d come to regret later
  • Understand how my shadow may be compromising my goals or the person I want to become and take action accordingly
  • Become less judgmental of others by conceding that oftentimes, what I’m judging is either an attribute I myself have suppressed or wish I demonstrate more of
  • Entertain those aspects of my shadow that may have been suppressed, such as the desire for adventure and spontaneity, which can be derived through regularly trying new things, weekend getaways and carving out space for serendipity by saying yes to those things I’d normally say no to
  • Share this post with the people closest to me so that they can better understand me and my behavior in an effort to support more transparency and strengthening of personal and professional relationships

Final Thoughts

Having said all of this, while I have indeed demonstrated all of the negative aforementioned shadow traits at some point, they are the exceptions to the rule. The overwhelming majority of the time I am the mask, which in many respects, is who I actually am; grateful for the life I have, disciplined, confident, responsive, purpose-driven, respectful and striving to be as virtuous as possible, which is, after all, an ongoing journey. As Aristotle said, “people should cultivate virtues at intermediate levels between deficiencies and excesses”. We are never perfect or ever truly arrive at being completely virtuous, we are forever striving.

Rather than striving to be somebody we’re not, we can all become a more authentic version of ourselves, and by being more authentic we can cultivate stronger relationships, become more likeable and magnetic, and have more fulfilling lives.