He is deemed the most innovative and successful business leaders in our era; she is an outstanding writer, with over 100 million copies of her books sold since the first of the decade-defining series was published in 2007. Born in 1955, in San Francisco, California, he committed his life to designing and in “making the best product” he could. 10 years later, she was born in a town with a population of about 20,000 people and was starting to exploring the literary world.

Later in their lives, both encountered their own fair share of life-defining failures, and just like any famous people who’ve “made it”, they cited their failures like badges of honor in their commencement speeches in Stanford and Harvard respectively.

Many may not make direct comparisons between Steve Jobs and J.K. Rowling, because they came from very different backgrounds, expertise, and industries. I only started noticing the similarities in the two successful individuals after browsing through their commencement speeches, one after another, in hope of finding motivation for a paper I was supposed to submit 24 hours later.

Freedom

The common denominator in both the speeches is how the word “freedom” was being brought into the picture.

They had said it after describing their failures.

Jobs mentioned his career failure and how it had become his most defining moment as a leader of Apple.

“I didn’t see it then, but it turned out that getting fired from Apple was the best thing that could have ever happened to me. The heaviness of being successful was replaced by the lightness of being a beginner again, less sure about everything. It freed me to enter one of the most creative periods of my life.”

On the other hand, Rowling described her life’s failure as a divorced parent and penniless.

“So why do I talk about the benefits of failure? Simply because failure meant a stripping away of the inessential.

I stopped pretending to myself that I was anything other than what I was, and began to direct all my energy into finishing the only work that mattered to me.

Had I really succeeded at anything else, I might never have found the determination to succeed in the one arena I believed I truly belonged. I was set free, because my greatest fear had been realized, and I was still alive, and I still had a daughter whom I adored, and I had an old typewriter and a big idea.

And so rock bottom became the solid foundation on which I rebuilt my life.”

Both cited freedom as a gift that only came after the biggest failure they could possibly have. To me, it was a refreshing way to look at the curveballs life threw their way. It is as though both of them were saying that the worst consequence of pouring one’s heart into one’s calling in life is unavoidable, but also an important lesson in courage and determination.

Imagination

Digging deeper, I found another similarity — imagination.

Both are highly creative individuals and had depended on their imagination to create their work.

In Rowling’s speech, the word “imagination” was explicitly mentioned:

“Imagination is not only the uniquely human capacity to envision that which is not, and therefore the fount of all invention and innovation. In its arguably most transformative and revelatory capacity, it is the power that enables us to empathize with humans whose experiences we have never shared.”

Jobs had not directly used the word in his speech, but we all know that without his imagination, some of us would not be holding an iPhone while scrolling this:

“You can’t connect the dots looking forward; you can only connect them looking backward. So you have to trust that the dots will somehow connect in your future. You have to trust in something — your gut, destiny, life, karma, whatever. This approach has never let me down, and it has made all the difference in my life.”

Two very different individuals had come to the same conclusion while giving advice through their life experiences. Can we extend this principle to life in general? Is this the secret to success?

Most importantly, why are we taught the exact opposite in most schools – to avoid these two biggest lessons in life – by “doing well in studies” and standardizing our way of understanding?

Failure: As a student vs in Silicon Valley

In Malaysia, I was the kid who could not comprehend the requirements of certain keywords in order to gain full marks, nor could I grasp the idea of learning by rote memorization, as we were tested on the ability to regurgitate answers. I could vividly remember being sent to the ‘B’ section of the class during my primary school days based on the class rankings (which was based on the aggregate examination results).

As a typical careless person, I made every mistake you could imagine – from spelling, calculations, to forgetting to bring my textbooks or completing my homework. I was once being caned for spelling “lion” as “lino”. Instead of feeling shameful, I thought that was a hilarious experience.

Yet as I grew up, I slowly learned how NOT to ask a lot of questions, and to NOT challenge assertions made by the ‘ones who know more’ – teachers, employers, etc. I remembered the sudden transition of requirements in education as I proceeded with college and university, where students were needed to be more vocal in their opinions.

Eight months into my journey as a National University of Singapore (NUS) Overseas College student here in the Silicon Valley, I started to question myself on the notion whether one is ever ready before crafting a solution, making a change, or creating a dent in the universe: is there such a thing as knowing enough before doing it?

Many of us have flirted with multiple ideas, yet the ideas stayed as ideas simply because we could not find a way to start them. Some may understand this as procrastination, but others may just sabotage themselves — “Am I even good enough to do this?”

Here in the Valley, there is a strong culture of people creating and documenting their portfolio online, a nascent display of their potential, and a substitute for the traditional resume. I am witnessing expressions of creativity and talent in different fields through a plethora of avenues – blogs, hackathons, open sourced projects, etc. Most of what is published aren’t perfect, but it was generally accepted as such, with some of these content creators even openly admitting to the imperfections.

Yet, it was still celebrated as a milestone to achieving something better in the next attempt.

Ending thoughts

People are encouraged to do the things they want to try and are reminded to make as many mistakes as they could. Interestingly, mistakes are considered badges of honor, and learning from them is the only way to learn how to be more efficient.

I was taught that only by having ‘skin in the game’ and starting on something one loves, only then can one truly master the requirements of a certain subject. Hence, there are projects, portfolios, and even personal ventures. These subjects do not have a fixed curriculum, nor do they have deadlines. As a contrast to school work, these are simply expressions of creativity, without the boundaries of marking schemes and formats. Sometimes, certain mistakes were prevented without certain ventures. That, to me, reflected what Rowling said in her speech – that by not doing anything because we thought we don’t know enough, and forgetting about it, we fail “by default.”

This stretches across the big idea on the contrast of education and innovation – if innovation is born out of mistakes and failures, could our education encompass the same concept by embracing imperfections in our projects, business cases, and presentations? Could education celebrate creativity instead of results?

Most importantly, could the culture of creativity drive the organic growth of innovation and support a country which is stepping towards the idea of being a Smart Nation?