Four years ago my grandfather passed away painlessly as he slept in his summer home on PEI. The summer before I had interviewed him and asked him what advice he would give to future generations. Here’s what he said:

Stay the course. If we had an example to lay down then it would be engrained in our kids, and it turned out to be the best thing since we now enjoy grandkids.

Of all the things he could have been thinking about, progress and family were the two that surfaced. My Grandfather saw his kids as the incarnation of his beliefs, and by that logic his purpose was to make the world a better place through the continuation of his family.

Eight months ago I was living a pretty static lifestyle working 9 to 5 in the shelter and protection of a large company. My identity was so tied to my job, lifestyle, and friends that it was defining me. Much of my extra thinking in the shower or on runs was pored into things that in hindsight weren’t all that important. Somehow the problems I was solving at work were getting in the way of focusing on becoming a better version of me. I was learning, but at a sluggish pace. And perhaps the scariest part is the former me perceived that pace as blistering.

Fast forward to today and I see a distant version of myself working that 9 to 5 and I think: he was pretty naive; and as I try to define the thing(s) that have changed, it’s difficult. So I look out into the world for similar patterns, and I find some. The patterns are sparse and un-connected, however a path begins to emerge, so I follow it.

It starts with small things that seem inexplicably authentic. Things that deviate from the norm, but in many ways are more reasonable. Is the software I’m running seeking new authentic experiences that deviate from its understanding of the world? What does authenticity even mean?

What is Authenticity?

The most common use of the word is in contrast to “fake” or “imitation”, however when describing a person as authentic, the word takes new meaning.

In Taoism: Taoists describe an “end state” they call the Tao, and often refer to the “Master”, an individual close to the Tao you should aspire to be like. The leading ethical concept in Taoism is Wu-wei, common translations are “nonaction”, “effortless action” or “action without intent”. The meaning is sometimes emphasized by using the paradoxical expression “wei wu wei”: “action without action”. The works of the original Taoists date back to 4th Century BCE, and seems closely tied to modern definitions of authenticity.

In Existential Philosophy: In existentialism, authenticity is the degree to which you are true to your own personality, spirit, or character, despite external pressures; the conscious self is seen as coming to terms with being in a material world and with encountering external forces, pressures and influences which are very different from, and other than, itself. A lack of authenticity is considered in existentialism to be bad faith.

In the void between psychology and biology: Perhaps what we perceive as authentic is just our expectation of “the way” someone “should” behave given the environment. If someone dies we expect people to cry, and if they do not, we perceive them as “inauthentically heartless”. In this way, perhaps our will to be authentic and seek authenticity is a hard wired instinct created out of necessity to assure our evolutionary path does not stray from morality or our sense of “togetherness”.

In mathematics: Authenticity acts as an attractor state. This state is a set of numerical values toward which a system tends to evolve, for a wide variety of starting conditions of the system. System values that get close enough to the attractor values remain close even if slightly disturbed.

“This above all: to thine own self be true, And it must follow, as the night the day, Thou canst not then be false to any man. Farewell, my blessing season this in thee!”

— William Shakespeare


There is a story told in buddhist folk lore of a monk in a village who decided to wear an off color tunic knowing he would be ridiculed for it. He willingly does this to enter a state of discomfort with his own identity. In his lack of comfort he learns more about himself than in the comfort his group identity grants him. If you ask most people who their hero is, you’ll often get answers like the single Mom who raised 2 kids with two jobs and a lot of perseverance. Perhaps some will say their hero is the olympic athlete who trained harder, suffered more, and willed themselves where others would not go.

We aspire to be more like those who thrive in discomfort, for in that discomfort lies truth.

Seemingly, the largest barrier to finding authenticity are the proverbial crutches we lean on to create our sense of identity. What’s more authentic: the corporate 9 to 5er, or the travelling backpacker? Crutches can be anything, from the people we hang out with, to the brands on our clothing, to the roles we play within our society. When you begin to kick out the crutches your safety net vanishes from under you and discomfort settles in. This discomfort may seem unbearable at first but as you remain there it slowly becomes more comfortable, bordering on pleasure. You’re forced to find your centre, the real “authentic” you.


Counter culture, deviance for the sake of deviance, and anarchy are examples of embracing the path while ignoring reason. It’s drawing a false conclusion that everything that is a norm should be reimagined. This is authenticity gone bad.

I think my grandfather found what he was looking for on his journey and his way of sharing his message with us was in his kids.

Now I’m finding my path.