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Breaking the Success Myth – Being the Relentless Iterator 
 

By Perry C. Douglas,
February 2, 2020

 
What’s your long-term plan? Where do you see yourself in five years? You need to quickly decide on your major in university. In order to get a good job and succeed, you need to specialize.  How many times have you heard those words, or how often have you told this to your own kids? Well, it’s all wrong! Evidence shows that most wildly successful people often try-test-and-continuously-learn and are prime time opportunists. 

As a student of history, I always tell my kids (while they roll their eyes…here comes another one of dad’s lectures) that most of the answers and wisdom they seek about the future can be found in history. Vincent van Gogh, for example, was a Dutch post-impressionist painter who was among the most famous and influential figures in the history of Western art. However, his most famous works were produced during the last two years of his life. Have you ever asked why? Was he a late bloomer? Vincent van Gogh failed miserably at many jobs before he took up painting. 

At age 16 he started as a trainee to become an art dealer in The Hague, he went on to do stints in London and Paris before he was fired in 1876. Next, he worked briefly as a schoolteacher in England, and then went back to the Netherlands to work at a bookstore.  In 1878, he went to the Borinage, a mining district in Belgium, and worked among the poor as a lay preacher. Less than a year after that he became a pastor, however the religious organization he worked for decided that he was not cut out for the job. His next career choice, artist; in brief, he began experimenting with sketches as he was now exposed to Impressionist and Neo-Impressionist artists, and started using lighter and brighter palette brushstroke techniques. The rest, as they say, is history. 

Facebook founder and CEO, Mark Zuckerberg, was certainly no genius or leader, evident in his current fumbling leadership of Facebook. However, he will go down as a legendary opportunist! Taking advantage of an opportunity put in front of him, in a fluid situation as two brothers essentially first came up with the social networking concept, while at Harvard. The brothers were slow-moving planners, arrogant and privileged. Zuckerberg was fast, shrewd and opportunistic. In the end, the two brothers received a $60M settlement for their trouble, and Zuckerberg went on to change the world and become a billionaire. You can comb through history, from Bill Gates to Muhammad Ali, greatness is primarily achieved from test-and-learning or seizing the moment, through the opportunities that appear in front of you or the ones you create yourself. Most of the great ones never set out to become technology billionaires or champion boxers, or iconic civil rights leaders; instead, time and place, and the courage to leap are what defined their success trajectory. 

Therefore, instead of telling our kids to live a structured life and follow the “success-norms” society has laid out, let them ask themselves the simple question: if it were so simple, then why isn’t everyone rich?  It is the curious and venturous that make things happen, the ones who see opportunity in complex problems; so, don’t be in a hurry to pick a major, explore different courses from the arts to science. Most critically, focus on your own very personal journey…after all, it’s your individuality that sets you apart from the crowd. Never follow that crowd, the crowd  is seldom right. The economy needs more free thinkers, those not afraid to step out of line, call injustices as they see them, the ones who are compassionate, and looking to succeed in the best interest of the common good. 
If you can do that, then you are already successful.  
 
It is really impossible to define one’s self from an early age. The reality is, the world has changed dramatically; we are in a new digital era, so, if you’re thinking the old way, then someone else will surely eat your lunch. Flirt with many versions of yourself which you want to become; don’t get tied down to the old conventional ways and thinking – work and society is different today. Recognize the change taking place around you; don’t be afraid to ditch the grand plan, strive to be opportunistic. Life is about time and place, the moment, so be well prepared when that moment comes; your entire life may be defined in what you do in those very moments.
  
Paul Graham, investor and one of the early funders of Airbnb and Dropbox and several other successful enterprises, said: “Most of the work I’ve done in the last ten years didn’t exist when I was in high-school…In such a world it’s not a good idea to have fixed plans.”

What he’s telling us is not to be complicit in NOT living your best life, by sticking to plans that may no longer be relevant to the new economy. One of the key attributes of highly successful people is adaptation and reinvention; this is also one of the basic principles of Darwinism…natural selection. Evolve and adapt, or die, or…settle and live an unfulfilled life. Graham goes on to say “…Instead of working back from a goal, work forward from promising situations. This is what most successful people actually do anyway.”
  
The depictions of genius, entrenched and specialized, making long-term plans, and executing without deviation is not an accurate image of how most very successful people succeed. Sculptor, Michelangelo, did not figure out in advance his final piece before he started chipping away, he actually tried and tested different things, and constantly altered his sculptures, and made many mistakes through curiosity and innovation. Art historian William Wallace points this out, as he tells us Michelangelo left three-fifths of his sculptors unfinished, every time moving to the more promising situation. 

We would be wise to advise our young people similarly, and ourselves too frankly, that in order to raise our game, we must constantly be learning and testing; and not from theory, but from practice. Start with ideas but don’t be afraid to ditch those ideas if circumstances change and new knowledge comes through discovery…opening up more ideal opportunities or better prospects. Don’t allow conventional wisdom to paint you into a corner, walk away, mess up the paint job. Try, test, and fail forward if you must…it will only be temporary. According to the author of the best selling book Range, “Michelangelo might have fit well in Silicon Valley; he was a relentless iterator.” This is how you find the best version of yourself, and only then, will you be able to master your game. 
  
Most people forget that having fun and enjoying what one does is a recipe for high achievement. In one of my favourite books of all time, “Relentless,” the story of how billionaire Ted Rogers built Rogers Communications; Rogers points out: “I have long been labelled a risk-taker, even a riverboat gambler, I don’t take myself too seriously. And I think more people in business should have fun....” However, to have fun you have to do the work first, in order to do what you really love. Accordingly, you must have the courage to think differently and stick to your convictions to get to the fun part. Find your authentic self, your true path; as the great leader Winston Churchill said: “Attitude is a little thing that makes a BIG difference.” “Success is not final, failure is not fatal, it is the courage to continue that counts.” Besides, “The only thing we have to fear is fear itself.”

Your greatness awaits…through relentless iteration and innovation in the pursuit of self. This is where the fun happens. Mahatma Gandhi so eloquently put it: You must be the change you wish to see in the world…happiness is when what you think, what you say, and what you do are in harmony.” In other words, if you are not happy about anything in your world or society, be willing to change it within yourself first. Don’t complain. Complaining won’t take you anywhere. Happiness comes when you find your own path, and the fun happens when you refuse to settle for others' expectations of what you should, and shouldn’t be doing, and instead live the life you know that is right for YOU. When your actions in life back up your words, when you know inside you are living true to yourself; that is when you can’t be anything but happy. Happiness lies in authenticity and integrity. This is also called freedom! 
 

What we think or what we know or what we believe is in the end of little consequence. The only thing of consequence is what we do”
                       
 – John Ruskin           


Perry Douglas,
Entrepreneur, Innovator and
Believer in Social Responsibility, and the
Good in Progressive Capitalism



 
 







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