The Great Riddle: fostering creativity and tenacity

This essay is adapted from a speech given by the author to aspiring entrepreneurs and engineering students at the University of Waterloo in 2012. It is what a psychiatrist might term an anxious mediation – a neurotic rumination of the author’s engineering education, the opportunities of technology, and his country’s role in a competitive and cutthroat global economy.

by Sheldon Fernandez
March, 2015

The car laboured listlessly down the highway, the mood soggy, my passenger perplexed. She was not familiar with this part of my life, the dark past to which I’d alluded but never explained. As I’d confess years later, a tad embarrassed, her gender was partly responsible for the wounds and the pain.

We made our way into the city of Waterloo, Ontario, and drove past the echoes of my anguished past: the Student Life Centre, the Davis Centre Library, Ring Road, the Columbia Town Houses, and the various buildings across campus. Perturbed by my eerie silence and perhaps sensing the red flags rolling through my mental rolodex, my girlfriend-passenger and future wife finally spoke up “what did this place do to you?”

I tried to describe to her in a roundabout way was the scar of trying times. Of nights spent in solitude with difficult mathematical concepts, cryptic computer code, and intractable exam problems. Of days wishing I’d spurned the study of Engineering in favour of Religion or Anthropology so I could revel in the carefree existence that college was supposed to be. And finally, of hours spent wishing I had more skill with the opposite sex, a longing that transformed into sadness when I realized the intricate workings of a microprocessor would not enchant the ladies.

Halfway through my undergraduate degree I went to see a good friend at the University of Loughborough in England, and came home dejected because the trip was so fantastic. Their carefree and cavalier lifestyle, the happy-go-lucky swagger, and yes, the women. It was the ideal college experience, I thought. A time to enjoy and relish real life before the tranquilizing drug of adult responsibility.

But propelled by an existential anger and the promise of better times, I, like hundreds before me, persisted through Waterloo’s gruelling Computer Engineering program and then rode the river of relentless ambition: I started a software company with peers that employs 700 people today. I completed a Master’s degree in Theology to use the ‘other’ side of my brain. I volunteered in the slums of Kenya to confront  humanity’s darker challenges. And I pursued creative writing at Oxford in an attempt to catch up with a liberal arts education.

Occasionally though, they would awaken, those troubling vibrations of years past: for however much pride there was, in triumphing against Canada’s top technical institution and the success that may have resulted, it was balanced or outweighed by an acute pain.

“A tad dramatic,” expounded my psychiatrist-wife years after this incident, her face half exasperated, half amused.

She was right of course, as wives typically are. In the scheme of things, it is indeed absurd to lament about the privilege – and that is the correct adjective – of attending a top university and struggling for the hard won deposits of one’s future. It’s a woe-is-me diatribe as vain as it is futile, an ostentatious exercise in shallowness. Yet buried beneath this impulse towards self-pity there lies a worthwhile story, a gradual metamorphosis of aggravation to appreciation, a coup over university demons and trifles unfulfilled.

As my inner Yeats might muse: thinking of glory and thoughts matured, I can say it was the scars endured.


Sheldon Fernandez recalls long nights of study in engineering at the University of Waterloo, while students in other faculties headed to the campus bar. It took him a decade to appreciate that if he lost something at Waterloo, he gained a lot more. Photo: University of Waterloo.

One of the classic documentaries from the 1990s is a movie called Hoopdreams, which follows the lives of two African American boys trying retrace the footsteps of NBA superstar Isaiah Thomas. Both live in the projects on Chicago’s South Side, and at ages 11 and 12 they begin attending St. Joseph’s academy – the same school Isaiah attended – in search of basketball stardom. In one of the film’s bleakest sequences, we see the boys rise at 5am on a cold winter morning to begin the ninety minute commute to Westchester. The street lights reflect off the hard winter ice and we realize what a long road – what plain hard work – is involved in trying climb to the top of the professional sports pyramid. More than anything, the movie is about the silent sacrifices that underpin greatness.

I often summon this theme when I contemplate my college years. I think of solemn walks to the library to confront differential equations while others were at the campus bar living it up. I recall the raw exhaustion in juggling a demanding course load, internship interviews, labs, assignments, midterms, and all the rest. I remember the palpable anxiety before final exams, when I knew that every ounce of my intelligence and ingenuity might not prevail against a cruel professor and crueller exam problems. I think indeed, of what plain hard work was involved in negotiating the obstacles of the country’s toughest engineering program and others like it.

I suspect many of my engineering brethren belatedly realized what it took me close to a decade to figure out: that if we lost something at Waterloo, we inevitably gained a lot more. Two precious jewels, in fact, treasures we embraced and drew upon long after our academic incarceration.

The thirtieth president of the United States got it right when he said: “Nothing in the world can take the place of persistence. Talent will not; nothing is more common than unsuccessful men with talent. Genius will not; unrewarded genius is almost a proverb. Education will not; the world is full of educated failures. Persistence and determination alone are omnipotent.”

Throughout my life I’ve listened to accomplished men sprout their secrets of success. Some enthralled with their eloquence and gusto, while others lobotomized with their torpor and cliché. Yet all their waffle and gusto could not detract from President Calvin Coolidge’s powerful point: that the recipe for achievement, significant achievement, is as simple as it is inevitable. More than equations and schematics, theory and technique, what lingers from my Engineering degree is this: the capacity for plain hard work, the propensity to persist, the strength when one is exhausted and discouraged to grind through the minutia of it all, through the obstacles, the naysayers, and all the stubborn hurdles of success. To, in the words of George Bernard Shaw, be a force of nature instead a feverish, selfish, little clod of ailments and grievances complaining that the world will not devote itself to making me happy.

Whenever I indulge in a self-righteous soliloquy on the persistence of engineers my wife shoots me an evil look, because as she often points out, we don’t possess a monopoly on determination. Doctors, lawyers, accountants and scientists are no strangers to perseverance and pluck. Which brings me to the second treasure of an engineering education.

Step back to August 10th, 1945, in Washington DC. It’s the aftermath of WWII, Japan has surrendered, and the allies have decided to split the Japanese-controlled landmass of Korea into two parts. An all-night meeting is convened at the Executive Office Building next to the White House and two young military officers – Colonel Dean Rusk and Colonel Charles Bonsteel – have been given 30 minutes – 30 minutes! – to draw a line dividing the two new countries.

For the first 10 minutes they can’t even find a map of the land, until an aide finally locates an old issue of National Geographic. And based on its out-dated atlas and their primitive understanding of the country, they choose the 38th parallel as a random and convenient way of dividing the peninsula. The Soviets, with more important things to worry about, consent to the split, and North and South Korea are formed.

There was tiny one problem, however: whereas the North got 50,000 square miles of dry and mostly un-farmable land, the South got twice the population and the most fertile rice fields. While the North suffered, the South flourished, and the division eventually led to the Korean War, a famine in the 1990s that killed somewhere between two to four million people, several periods of tension and tribulation, and many of grave challenges that confront the global community today. All because of a random line drawn by two of history’s forgotten men in an obscure office over half a century ago.

As a student of history, one sees this pattern again and again, random, happenstance moments in time that snowball into events of incredible magnitude and significance; what mathematicians and weather scientists term the Butterfly effect,1 the idea that the tiniest fluctuations in a complex system can have colossal implications. The oscillations of history cut in both directions – sometimes for the greater good and sometimes not, but at this moment, in a certain context, they are colluding to the advantage of those proficient with technology.

Somewhere in my parent’s basement is the 386 Compaq computer I first learned to program on, and somewhere inside that computer, sits the 14.4k modem that connected me to the outside world. Back then, the Internet in its modern form did not exist and some readers may recall Bulletin Board Services – or BBSs – that were like virtual electronic communities, places where one could chat with other users, download pictures and software, and generally just waste time. And from this obscurity, arose the digital world as we know it today.

It’s strange to reflect on that primitive era when the foundations of the Internet first blossomed, because I don’t think anyone thought that these tools, these hobbyist constructions, these little 1s and 0s flying over phone lines, would transform global economies and communities to the extent that they have.

Whether by chance, coincidence, or the simple evolutionary quirks of our species, technology and applied science have become the golden hammer and chisel, tools to revamp whole industries and birth entirely new ones. As I’ve discovered, proficiencies with this language can bring one to some amazing places. In my case, from the slums of Kenya to Paula Abdul’s house in Beverly Hills, from a meeting with the President of Fox Media in Hollywood to sitting with members of the royal family in Abu Duabi. Few would argue today that the technology butterfly is flapping with full force.

To return to the basketball analogy from earlier, the two jewels of engineering – technical know-how and the raw determination to wield it – make our young engineers top draft picks so to speak, our next entrepreneurs, idea-generators, architects, and dreamers. But like top draft picks, they are just beginning, still to play the game with the big boys for big stakes and big money. So what advice can I, a player half-way through his career offer our young crackerjacks in-the-making?


Not everyone is an entrepreneur, though many readers may be so without realizing it. The word itself means different things to different people, but I prefer the sentiments of the aforementioned playwright who said: “some people see things and ask why, but I dream of things that never were and ask why not?”

Stripped of the decoration and fluff, what I’ve discovered is that the entrepreneur’s soul is move by two complementary forces: refusal and audacity. Refusal to be limited by the world as presented to them, which then blossoms into the audacity to transcend it.

I often warn new graduates and aspiring entrepreneurs that this road it is difficult and exhausting because creation and change are never easy. I further inform them that comfortable jobs with six figure salaries await most of them after university. But I also encourage them to envision life many years from now when they are older.

Ignoring the resulting grey hair and wrinkled skin, how would they describe the first decade after graduation in hindsight if they didn’t have to be pragmatic or realistic? What adjectives would they use? What triumphs would stir their souls? Would it be an incremental contribution to a software giant, which is a practical, respectable, and comfortable road? Or would it be something more, an opportunity to look back on their lives many years from now and claim “I did that, that’s my creation”.

This is a highly personal question, but I share with budding graduates two secrets. First, there are few things in this world more professionally satisfying than seeing your own vision made real. To others it will seem like magic or luck and they will fawn over your achievements and ask how you did it. And in your heart of hearts there will reside a quiet and lasting satisfaction because you’ll know the truth: that it wasn’t magic or luck but plain hard work over several months and years; the small sacrifices, the struggles and the sweat endured in solitude.

And secondly, even if you fail in traversing this more difficult path you will succeed because of what you learnt in throughout the journey. One of the most successful entrepreneurs I know once told me: you learn business not by pursuing an MBA, but by simply starting your own business. True leaders do not step into the ideal ecosystem, it crystalizes around them because of their presence. The perfect place and time does not exist. So be somewhere, shut up, and just do it.


Beyond this call to entrepreneurship, there is an additional theme that warrants exploration, a dynamic dear to my heart.

For three years I worked at the Accelerator Centre2 near the Waterloo campus as the head of our company’s angel investment arm. One day, the owner of a large VC from New England toured the building to see what Canada’s brightest minds were working on. He was a millionaire many times over, and toward the end of his visit he made a revealing comment.

“You Canadians” he said “are so courteous and polite, but you don’t think big enough. Most of you would be happy creating a 30 or 40 million dollar company, whereas your counterparts in the America define success as a 3 or 4 billion dollar enterprise”.

Indeed, there is a lot behind his words.

During my time at Waterloo the media was abuzz over the so called ‘brain drain’ – the belief that Canada’s top minds were leaving the country and taking their talents down south, and as someone who did internships in New York City and Silicon Valley I’m proof of that fact. And yet, as the partner of a company with head offices in Manhattan and Toronto, I also know that many of our Canadian employees return to the homeland after some years abroad.

The majority tell us it’s because of family and friends or that they simply miss home: Tim Hortons, Swiss Chalet, Ketchup chips, and Hockey Nights in Canada on the CBC. Yet I would submit that the reasons are deeper and more subtle.

“Life, liberty and the pursuit of happiness” reads one of the key phrases from the American Declaration of Independence, the calculus of capitalism distilled into seven simple words. Yet take note of its individualistic flavour as it envisions a world centered on the fulfillment of personal potential: your right to a higher education, his right to equal pay, her right to choose.

Now consider the competing words from Canada’s constitution act which articulates our ideal as: “peace, order and good government”. Embedded in this phrase is the expectation that our responsibilities for the collective and for our communities are as important as the impulses we might hold as individuals. Implicit further are other words like ‘civility’ and ‘moderation’ that embody our Canadian way of life. And together they allude to Canada’s commitment to human rights, tolerance and diversity which make our country one of the most sought after destinations in the world.

That said, think about how these differences might manifest themselves in an entrepreneurial setting. America’s emphasis on the individual is tied to the belief that a person’s altitude in life should be determined solely by their effort and talent. It’s the American dream personified and the building-blocks of their more perfect union: that anyone can rise to the desired level if they would only have the courage to do so. With such a foundation, should it come as a surprise that so much invention and significant achievement – the Microsofts, the Googles, and the Facebooks – originates from our neighbours down south? If entire populace is engrained to dream without restraint, then at least a few of those dreams will come true.

But what about us Canadians? Polite, courteous, cautious Canadians? There is something to the generalization that while Americans are concerned with monetary successes, Canadians are concerned with quality of life. I see it every day at my company when our top employees forgo substantial US salaries and return to Canada for less money. I see it in our Toronto office where my best and brightest people opt for quieter careers with less travel so they can spend more time with their spouses and children.

I can’t fault my employees for these decisions, and on a human level their priorities make me proud even if they complicate our business. But how do you remain globally competitive if your killer instinct isn’t quite as sharp as the competitions’? How do you innovate and persist? Indeed, how do you foster creativity and tenacity in a moderate society? As Shakespeare said, therein lies the rub.


Six billion dollars – that is what the government of Russia is spending over the next three years3 to convert 900 acres of farmland near Moscow into a technological oasis. By the end of this year, the cows grazing on this land will be replaced with 15,000 scientists and entrepreneurs in hopes of creating the next Silicon Valley. Tunisia has made similar vibrations as they attempt to become the Arab standard-bearers of innovation. Both countries recognize – as do many others – that technical innovation in the private sector will fuel the economies of tomorrow.

But we return to the original dilemma: can you artificially replicate the American spirit? Can you recreate the special ecosystem of the real Silicon Valley?

After grappling with this puzzle for some time, I realized that the question might be misguided, and the inquiry we might instead ask is: how do we turn our unique Canadian values to our entrepreneurial advantage? Is it a matter of defining success differently than our American counterparts? Is it focusing our technical talents on problems that intersect with our country’s emphasis on the community and human rights? Is it also confronting the darker sides of unrestrained capitalism? For example, while many observers celebrate the incredible accomplishments of Apple Computers, few examine the thorny issue of Chinese labour exploitation4 that made these accomplishments possible.

To my fellow engineers and the entrepreneurs of tomorrow I say: your education and hard work have gifted you the wonderful option of earning a living to daydream and create should you choose. I’m not going to ask you to think more ambitiously or expansively, but I am going to implore you to think more ‘Canadianly’. You and your colleagues have considerable sway in shaping the Canada of tomorrow, so the real question, the crucial inquiry, is in fact very simple: what type of country and world do you wish to pass on to your successors?

In my last two years at Waterloo by pure coincidence I began working with a professor in the Optometry Department and using his research we devised a system that could diagnose the refractive error of individuals unable to communicate with an optometrist. This had been a long standing problem in the field especially for children and disadvantaged persons who could not read. Although the practical benefits of the system were substantial, what struck me was that the engineering work itself was relatively straightforward.

This undertaking highlighted a most discouraging reality: the industries that might most benefit from technical know-how – medical, environmental, humanitarian – will rarely profit from the fruits of engineering ingenuity. One can probably guess why, as the financial rewards of writing an iPhone app for a bank or Fortune 500 are considerably greater than doing the same for an NGO or Optometry professor.

Seven years ago I spent some time volunteering in the slums in Kenya and promised myself I wouldn’t touch or use a computer during my stay. It would be cathartic, I thought, to leave the engineering-Sheldon back in Canada. Alas, fate had other plans. The organization required infrastructure help, teachers needed PowerPoint training to better educate women on the realities of HIV and AIDS, and the orphans wanted to write not with pencils, but in Microsoft Word. Quite simply, the impact I could exert as an engineer outweighed by an order of magnitude that which I could exercise as just another helping hand. So on day two, engineering-Sheldon returned, and my colleagues in Nairobi were soon using Facebook and MySpace to draw attention to their causes.

Is there a purpose to these anecdotes, other than to perhaps highlight a unique Canadian-ism about our concern for the marginalized and persecuted? I can speak only from experience and suggest that simply acquainting oneself with the troubling aspects of our humanity – the egregious violation of human rights in places like the Congo and North Korea, for example – will in some intangible ways make you a better entrepreneur, if not also a better person. As a Waterloo alumni, it gives me tremendous pride to recall that over a decade ago two of our graduates, George Roter and Parker Mitchell, foundedEngineers Without Borders5 to address these very challenges.

Finally, I want to emphasize that while our values may differ from our neighbours down south, there is much we can learn from the tenacity of the American spirit. Thus instead of being content with a 30 or 40 million dollar venture, perhaps the goal should be a 3- or 400 million dollar one, not for the sake of wealth itself, but because of how such wealth can be exerted. Think of Blackberry founder Mike Lazaridis’ ambitions with thePerimeter Institute for Theoretical Physics6 on the Waterloo campus, or the celebrated philanthropy work7 of Bill Gates.


Towards the end of his life, Michelangelo said “the sculpture is already in the rock, it is only for me to bring out”. The creative act might be the most difficult act of all because the world does not take kindly to novelty or newness. This is true of art, philosophy, politics, and, yes, the applied sciences.

Melodramatic indulgences aside, if there is one thing I want you to take away from this anxious meditation, it’s the courage to create Canadianly.

So fear not the naysayers and doubters and just create, emphatically and with unapologetic grandeur.

Create, with the resilience of an American, the sensitivity of a Canadian, and the integrity of a gentleperson.

Dream with audacity, design with intelligence and execute with resolve as you search for that next rock, and that next sculpture to make real.

Copyright Sheldon Fernandez 2015 


1. Butterfly effect, Wikipedia:
2. Accelerator Centre:
3. The Next Russian Revolution, The Atlantic:
4. Apple ‘failing to protect Chinese factory workers’, BBC:
5. Engineers Without Borders:
6. Perimeter Institute for Theoretical Physics:
7. Gates Foundation:


Sheldon Fernandez

Sheldon Fernandez

Sheldon Fernandez is a self-described football fanatic, computer engineer, humanitarian, and aspiring artisan.  He can be reached at: His previous pieces for Facts and Opinions include One day at Wembley: a soccer fanatic reflects and  My Last Day in Kenya.















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