I Wish School Taught Me That Careers Are Non-Linear


“Do not go where the path may lead, go instead where there is no path and leave a trail.” — Ralph Waldo Emerson


Steve Jobs, the former CEO of Apple, died at the age of fifty-six. During the early part of his career, Jobs was extremely reluctant to discuss his family background in public. But the commencement address he made on June 12, 2005 to Standford University graduates, gave the public a rare insight into his personal life. I must say, after listening to a recorded version the other day, I was intrigued, because this is destined to be regarded as a classic.

Steve Jobs dropped out of Reed College after the first six months. Two years later, Jobs and his partner Steve Wozniak, started Apple in his parents’ garage. In ten years, the company had grown from just the two of them in a garage, into a $2bn company with over 4,000 employees. And then he got fired. What the heck? How can someone get fired by the same company he helped found? It turns out Jobs hired John Sculley, who had been CEO of Pepsi, the drinks company, in the mistaken belief that having an experienced chief executive would free him to do what he really loved doing – which was creating great products. His pitch to Sculley to persuade him to leave Pepsi was:  “John, do you really want to spend the rest of your life selling sugared water?” Later, when their visions of the future began to diverge, eventually, they had a falling-out. When they did, the board of directors didn’t side with Jobs. He was out, publicly.

In the short term, appointing Sculley looked like the defining, catastrophic error of Jobs's life. But later on, he came to see it differently. The idea that getting fired might be a bracing idea to start something new. “The heaviness of being successful,” he said, 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.”

During the next five years, Jobs started the company NeXT, and another called Pixar. In an unprecedented turn of event, Apple bought NeXT, and Jobs was back with Apple. He then became Apple’s CEO until his death.

Life takes us to many places, and I’m certain that Jobs didn’t plan on quitting college to start Apple, nor did he plan on getting fired by the very company he found, only to become the CEO again later on in his life. Of course it’s impossible to connect where life will take you looking forward. But it will be very clear looking backwards years later. So it seems to me that the journey is truly more important than the destination.

Not many of us are as bright and lucky as Steve Jobs. But perhaps, there are a few things we should be aware about life and career that no schools would teach. Let me explain.

The Linear Myth  


The traditional career path is commonly referred to as the linear ladder. It is a series of continuous promotions in title and salary, in a specified industry over a period to time. You’ll feel an immense feeling of satisfaction and achievement when you reach some sort of career pinnacle. Plus, you’ll earn the prestige and high salary of course. However, people who’ve reached their peak, or close to it, seems to be unsatisfied with many aspects of their work.

I know people who love consultancy and adventure but are unhappy spending their working hours writing drudging letters and proposals, because a promotion in their organization means prioritizing their employer’s needs.

I know people who love research and problem solving but are now stuck managing people, because a promotion in their field means taking on a senior management role.

I know people who love writing and community building but are busy editing and sitting on committees, because a promotion in their line of work means they are now responsible for the company’s fiscal health.

Improving your career is important. Don’t get me wrong. But when we climb the linear ladder, we often end far from the actual work we love doing.

Contrary to the people I mentioned above, I’ve also met people who are able to improve their careers and enjoy their work at the same time.

Before my friend John launched his writing career, he hustled two jobs: nurse by day, copywriter by night. Fast forward, today he is a firefighter during the summer, and when winter comes, he retires in his cabin and writes full-time.

Dr. Chen was once a bored General Practitioner. In less than five years, she transformed her career by learning the techniques of Traditional Chinese Medicine, and combining it with her Western Medicine craft. Now, she practices in Shanghai from March to August, and would move to Australia during the months of September to February.

And how can I forget my mentor Ben - who’s taught me a lot. Before his family immigrated to Singapore, he had to build a new client base, spending time and energy traveling back and forth between Boston and Singapore every weekend. It took him three years before he could finally close his chapter in Boston. Today, he manages his own business.

Very few people are able to manage themselves, and importantly, their careers. Those who do will always be a minority. The majority will keep what they are doing now, that is, retire on the job, continue being bored, mindlessly following their routine, and counting the years until retirement.


Mobility: Carving Your Horizontal Path 


I believe a job that teaches you nothing, is just a job. And because it teaches you nothing, you’ll remain there. And soon, you’ll get bored - unless you do something to change it.

You know, many employers don’t give a damn about what you think. They only care about your energy. Your manual labor. The truth is, you’ll be a more valuable asset when people care about your intellectual thought. If all you’re selling is your labor, you’re selling yourself short. The modern economy is built upon knowledge.

“There is a change in the nature of economy from a material-based economy to a knowledge-based economy. The main assets in the past were materials like gold mines or wheat fields,” said history professor and best-selling author Yuval Noah Harari. “These are the types of things you can conquer through violence.” So the only way you can invest for your future is to invest in yourself.

Fortunately, we’re not holding back by the lack of ideas, rather the lack of execution. We tend to wait for someone to give us permission. Well, it’s time to give yourself permission. Learn to love yourself before realizing your employer stopped caring about you a long time ago.

There are two types of workers in the job market: manual workers and knowledge workers. Taxi drivers, nurses, and construction workers for instance, represent the manual workforce. They are the physical and mentally tired workers who are capable of functioning despite all kinds of minor complaints.

Lawyers, doctors, and business executives would constitute the other half of the spectrum: the knowledge workforce. They are good at what they do because they possess valuable skills for their organizations. Some of them are regular contributors to the community. But the most common thread: they love challenge and the pursuit of satisfaction.

In the current state of the global economy, machines are slowly taking over the manual and knowledge workers’ monotonous and laborious duties. Not to mention, everyone is dying to escape from day to day boredom and end their working life expectancy, then move on, that is, reach retirement and spend the next ten or fifteen years doing nothing, playing golf, going fishing, engaging in a new hobby, and so on. It won’t be far in the distant future until we see self-driving vehicles roaming the streets of Manhattan or Shanghai.

Because of this issue, there is a greater need for people to prepare and have mobility over their careers. Now, it would be easy for knowledge workers in their mid-thirties to explore other avenues and reinvent themselves into a completely different individual. It is another story for a taxi driver in his fifties.

Luckily, there are ways for any individual to mobilize into a new career:

First, is to actually start a totally new and different career. Typically this would mean moving from one line of work or organization to another.

There is a substantial number of middle-aged women in the United States who have worked for twenty years as a middle-level management position, and now, at age forty-five and with the children grown, enter law school. Three or four years later, they then establish themselves as small-time lawyers in their local communities.

Your author can also attest the effectiveness of this concept because he has done it. Before pursuing my passion for education, I was in an entirely different profession. As an Optometrist, I got bored really quick. It didn’t take a decade for me to realize that Optometry wasn’t my life’s calling. After a two-week visit to China, I immediately fell in love with the country. In less than a month - and armed with three teaching credentials - I then landed a job educating children.

Second, is to develop a parallel career.

There is a growing number of successful people in their forties or fifties moving from working full-time to being part-time employees and become consultants in their field of interest. One example is Dr. Mehmet Oz - the notable cardiothoracic surgeon - better known as Dr. Oz, has turned himself from attending his full-time surgical practice to a media mogul and author of many bestselling books.


Finally, the third, is to do philanthropic work.

People who are very successful in their first career as attorneys, as business executives, as university professors, and love their work, but it no longer challenges them, may start something new, and usually a nonprofit activity. In other words, they’ve turned themselves into social entrepreneurs.

Most social entrepreneurs began working on their chosen second enterprise long before reaching their peak careers. One university professor, for example, began to do volunteer consulting work in local schools when he was thirty-five. He got elected to a school board at age forty. When he reached fifty, he started his own enterprise to build and run model schools. He is, however, still working nearly full-time as senior professor in the same university he had worked since a young age.

It all boils down to this: if you work hard at your job, you make a living. If you work hard on yourself, you make a fortune. What is the reason for this truth? Success is not something you pursue. Success is something you attract by becoming an attractive person. The way you become rich is not by wishing your life were easier, but instead focusing on making yourself better.

Credentials Don’t Matter; Reputation Does 


My high school English teacher, Mr. Sidlecki, once addressed the class: “Why don’t people put their degree initials after their name? I mean, should people put 'MA' after their names?” At first, I thought he was joking because the initials meant these people were from Massachusetts.

Then I learned that the initials signified “masters of arts,” and I have never seen that degree used after someone’s name in any other milieu. I can string a few initials after my name from racking up three degrees and half-dozen certifications and licensures. Meanwhile, I still encourage my students to call me William, not teacher. I don’t even like being called mister.

The truth is, there is a plethora of degrees beyond the scope of your imagination: BBS (bachelor of bakery science), BAP (bachelor of arts in puppetry), MSW (master of social work). There is also the alphabet of certifications, memberships, and strange relationships that I think is nothing more than a desperate attempt to engage in the bizarre ritual of ACBAI (adding credibility by adding initials).

Of course there are people who will tell you that “credentialing” is the credibility statement of the future. However, it seems to me that they are empirically wrong. There are so many of these loony honorifics today that someone with a brain should be skeptical. Perhaps, my former mentor was right all along when he said, “You know what BS stands for? Bullshit! When you have an MS, it stands for more shit! And a PhD is actually short for piles high deep.”

We spoil ourselves all the time, especially when we’re privileged. Take a stroll into any private doctor’s office in Singapore, and you’ll be amazed by the graceful plaque degree assembly on the wall that should speak for itself. You wouldn't even consider consulting before thoroughly googling the good doctor's credential. But would you enquire prior to being admitted into the emergency room? Would you ask, “Hey Doc, where did you go to school?” You wouldn’t care whether or not the doctor is a resident who nearly dropped out of medical school, because you’re being put in a life threatening situation.

Similarly, don't expect to find a single credential hanging on the wall inside a Michelin Star Tokyo sushi joint which meticulously states who mentored the sushi chef and which academy he attended. You’d be stupid enough to ask. Sushi creation and presentation are the “masters of art” no word nor degree could describe.

Before I could start teaching in China, I had to pass three teaching certifications. The school I worked for didn’t even care about my previous degrees. And when I finally quit slaving for the school and began working for myself, those credentials became a thing in the past. I never had to use any of them, even when taking on a new client, because my organic relationship is built on trust.

What does matter is a track record, which cumulatively, assembles as one’s reputation. If you’ve been doing what you’re suppose to, you should have established your name as a brand, or brands. The bottom line: if your client or customer doesn’t recognize the credential, it’s worthless.

Adventure is Worth More than Money 


Throughout my career, I pursued jobs that I enjoyed doing. Love of work was my number one priority. In fact, it was more important than the job title or salary. As I discovered new challenges, I switched jobs every two years on average.

Like many American teenager, my first high school summer job was flipping burgers. By the time I finished my three months probation period, I wanted a more challenging job with greater responsibility, so I quit the burger flipping business. In less than a week, I landed a new job as a museum tour guide. But that didn’t kept me busy enough. As a result, I also picked up a volunteer position at the prestigious Boston Medical Center.

The two jobs kept me busy into the first two years of high school. In my junior year, I became interested in becoming an eye doctor, and luckily, I got an internship position with an Ophthalmologist. She taught me a lot.

After graduating from high school, I had more freedom during my college years, and was able to pursue other avenues. I became a strength coach for a division one football team to rack-up extra cash. I’ve also worked with my uncle as a dental intern. I even became a teacher’s assistant for the Veteran’s Science Program at my university. All that job hopping made my parents worried, to the point where they’ve assured me to pursue a more “stable” career. I’d still pondered about that old interest of becoming an eye doctor, so I went to Optometry school - which makes perfect sense to me at the time because my parents gave me the privilege to continue the family’s eye clinic business. Unfortunately, my pursuit for the “perfect” job turned out to be a big mistake.

Two years going into the job, I realized the many boredoms that surrounded me every day. I had no passion. I felt that I worked to fulfill my parents’ need, and the fact that I was living someone else's life. What can I do?

I began my journey with a backward glance. I scouted around my childhood. What were the things that I liked to do? What made me happy? Then I remembered that I used to fantasize about being a teacher. When I was eight, I'd bring my dad's old briefcase and filled it with books, papers, and pencils. I'd have a small blackboard with colored chalks and I'd have my bears and dolls as the students in my class. I got even more excited when I remembered I had some volunteer and teaching experience with both children and adults back in my school days.

Today, I live and work in Shanghai, China’s busiest metropolitan city. Looking from the hilltop, many of those jobs had even a hope of any practical future in my life. They were the typical mechanical jobs people often pursue on a short-term basis; Optometry being the exception. If I had never taught kids and adults back then, it would be almost impossible for me to have the slightest idea about being an educator. If I didn’t quit Optometry and took that two-week trip to China, I would have never discovered what I truly love doing.

Just as the expired taxi driver must learn to reinvent himself, we too have a responsibility to manage our lives and our careers before it’s too late.

As Bill Gates once said, “Flipping burgers is not beneath your dignity. Your grandparents had a different word for burger flipping - they called it opportunity.” And personally, for me, opportunity comes when I savor the adventure. Life is a pathless land. The most important thing is to set sail and ride the course. Because in the end, the destination is irrelevant. The point is to enjoy the journey, not predicting the correct outcome in the future.