Beyond PEAK COLLEGE: 4. Charting Your Own Path

He who has a why to live can bear almost any how.

~ Nietzsche

Just a few years before he died of cancer, Steve Jobs, one of the most iconic business leaders of our time, shared with us how he understood his own life story. He was famous for having dropped out of college, seeking spiritual enlightenment in India, and then returning to the U.S. to start Apple Computer (with Steve Wozniak), which revolutionized personal computing. Before Stanford’s graduating class of 2005, he tried to make sense of the many twists and turns that his education and career took (including a very dramatic and very public firing from the company he founded).

The seemingly accidental and unrelated events in your life, he offered, are dots that eventually connect. As an example, he talked about how dropping out of Reed College allowed him to audit a calligraphy class that later made the Macintosh distinctive as a personal computer. “You can’t connect the dots looking forward,” Jobs said. “You can only connect them looking backward. So you have to trust that the dots will somehow connect in your future.”

As one of the leading iconoclasts of our time, why was it important for him that the dots connect? What was he trying to say to the younger generation of “crazy ones, the misfits, the rebels, the troublemakers, the round pegs in the square holes?” What did he believe it really meant to chart your own path in life, which he so famously did?

His insights may be useful for young people who will have to chart their own path, post-peak college.

First, we should consider what “charting your own path” typically means for a young person about to leave high school. You find yourself at a crossroads where you need to decide whether to do what your parents (and society) expect of you, or something else. Do they want you to go to college? If so, which college? Do they want you to join the family business or go into the military?

Their expectations have been pounded into your head for years and they often have the weight of history, tradition, and duty behind them. Your decision, as you’re about to leave high school is whether to meet those expectations or rebel against them. Many of you will find yourself having to react against parental and societal expectations, even if you don’t know for sure what you would do instead.

In my case, I went to University of California at Berkeley thinking I would major in something science-related. That was as specific as I got. It wasn’t because my parents told me I should. It was simply a cultural norm that I had accepted as a foreign student from Taiwan. My parents were paying a fortune to send me to go to school in the U.S. and I wanted to take the education seriously. I did well at Berkeley and maintained a B+ average. I even volunteered in a lab to get some hands-on experience in scientific research.

But in June 1989, right before I had to declare my major in my junior year, I went to visit my parents in Taiwan. On mainland China, students were gathering at Tiananmen Square to protest and demand democratic freedoms. As their numbers grew and talks broke down, the government sent in tanks and brought the protests to a bloody end. CNN carried the whole event live on TV until it was forced to end its coverage. I remember being glued to the TV day and night to watch the drama unfold.

Something sparked in me. I realized for the first time that there were these era-defining stories playing out in the world and I wanted to be part of them somehow, not holed up in a lab doing experiments that take years to bear fruit.

When I returned to school, I decided to volunteer at the news department of Berkeley’s radio station, KALX. It involved waking up every morning at 5:30 and biking to the station in the dark to produce the morning newscast, which would go on air at 8 o’clock. My new interest would consume many hours of my free time but I loved every minute of it. Very soon, I knew that journalism would be my path and proceeded to declare English Literature and Rhetoric as my majors. I turned away from cultural and family expectations. I was doing what I loved and following my passion. Or as the mythologist Joseph Campbell would put it, I was “following my bliss.”

I never regretted that decision. It led me, coincidentally, to work for CNN, the very news channel that had derailed me from my original path. I started as a writer and soon became an on-air reporter for the network’s educational newscast and then a producer for one of its primetime newsmagazines. Working out of CNN’s headquarters, I got to be involved in many of the biggest stories in the 1990s and even circumnavigated the world by ship to produce a 10-part series on some of the key issues we faced at the end of the millennium. It was as interesting a job as I could ever expect.

It so happened that the story that got me the most attention at CNN was a profile of photojournalist, Dan Eldon. After his tragic death in Somalia, his mother published pages from his 17 volumes of artistic journals. They showed the life of a unique individual who lived passionately and used his creative skills to help people in need. Although he died young, he had made a real impact on the world stage and inspired countless young people to rebel against the norm as well. His motto: The Journey Is the Destination.

I may have been drawn to his story because it validated my choices and inspired me to keep taking risks.

Soon, though, I began to face the complexities of “following your bliss.” For some, it means choosing one well-trodden path for another (i.e., becoming an engineer instead of a doctor). For others, including me, there didn’t seem to be a clear path in sight. Not anymore.

What often happens, I learned, is that either the world changes or you change.

The longer-form journalism I did at CNN made me want to do more in-depth storytelling. So I left to produce a new series for PBS — coincidentally, with Dan Eldon’s mother and sister. (Many more dots in my life have flowed from this one story.) That series, GlobalTribe, opened my eyes to a new world of people known as “social entrepreneurs.” I was enamored by the possibility that one could devote one’s life to solving social problems with an innovative rather than a charity mindset. I was especially moved by the young people who were stepping up to lead adults in their communities.

One group in particular called themselves Eco-Punks, or more formally Tierra Viva. What brought them together is their love for punk rock, which they performed regularly. But in their free time, they also used permaculture practices to make Mexico City’s urban slums less polluted and more livable.

After getting to know many leading changemakers around the world, social entrepreneurship became my new North Star. There was just one small problem: there didn’t seem to be any defined pathways to social entrepreneurship. I had to make my own way.

I started by creating a new charity, Global Youth Fund, in Vancouver, Canada, and introduced a new democratic approach to how young people engage in social change. Rather than rely on their teachers to tell them how to create change, students taught one another and learned to harness their collective wisdom to design world-changing projects. We piloted the program in three countries and demonstrated that young people can lead more effectively when they learn to be inclusive of diverse perspectives.

My work got the attention of Ashoka, the world’s largest network of social entrepreneurs, and I decided to join their global team and help them expand their youth program. That in turn led led me to work for one of the most innovative funders in youth empowerment, Fossil Foundation.

It’s not easy to give my path a name or to recommend the steps I took to anyone else. Another person in my field, social innovation, will have a very different story.

I do believe, though, I have learned a few lessons that are common to others who have charted their own path in my or any field.

1) You unlock new opportunities with passion, not credentials.

In 2001, when I produced the PBS documentary series on social entrepreneurs and decided to follow their steps, there was no school I could go to and no credential I could earn for social entrepreneurship. Few people even knew what the term meant. But there were more and more organizations funding social entrepreneurs through grants and fellowships. What I had to demonstrate, first and foremost, was a strong commitment to the new practice. I had to have a clear sense of WHY I do what I do and what I had to contribute.

People who take a risk on you — your funders, employers, clients, and partners — want to know when the going gets tough (and it will), you are committed enough and capable enough to see things through. They also want to know your passion will keep you learning so you can continue to improve what you’re offering. They’re not just betting on your idea, which can change. They’re betting on you. So it has to be evident you are passionate about what you do.

It’s now in vogue to criticize passion. You will hear many successful people dismiss passion as nonsensical or even misguided. They believe you need to get good at something and then passion will follow, if it ever does. It’s true that just loving something isn’t enough. You need to have skills. You need to be able to do add value, however that’s defined in your field. Passion can’t just be a feeling.

But it’s also true that you can’t persist if you don’t like what you do or don’t feel strongly about it. However you arrive at passion, it’s important you get there. Passion is not all you need. But you can’t not have it.

2) You move forward by teaching yourself new knowledge and skills.

If you are working in a field that’s truly new (and you haven’t simply chosen an alternate well-trodden path), then you will have to teach yourself. You have to be insatiably curious and learn all you can to achieve your goals. No one can give you the definitive curriculum for what you need to learn. You will have to construct the curriculum as you go and fill in gaps of knowledge when you see them. As the popular saying goes, you need to build the plane while flying it.

I’ve had to teach myself many new skills, including how to measure social impact, how to read financial statements and create them, how to calculate an organization’s growth rate, how to write grants and grant reports, etc. These are just some of the technical know-how needed in my current field of philanthropy.

There’s deeper learning as well around how to involve diverse groups of people in your work, especially when your work impacts them — in other words, how to design solutions with, rather than for. I had to learn this through countless interactions with other changemakers whose paths I’ve crossed over the years.

You are always learning from others and they from you.

I have gravitated toward fields where teaching yourself can take you places, where credentials don’t matter. So far, it has worked. Just from teaching myself, I have been able to work for leading global organizations in three different fields. Formal learning can get you started but self-directed experiential learning is how you advance.

3) What we seek, ultimately, is meaning and purpose.

Charting your own path is different from hustling, even if it can look that way to others as well as yourself. What we want from the many opportunities we involve ourselves in is that there’s a point to most of it. We want to know they are taking us to a good place and that they “add up” to something significant in our lives.

When I switched from journalism to social entrepreneurship and then philanthropy, I saw each transition as a next step toward making a bigger difference in the world and helping me better understand how I want to contribute to society. Each phase builds on the one before and paves the way for the next. Everything I do now draws on everything I’ve done. They all blend together.

In between the different chapters in my career, there were gaps that sometimes stretched months or up to two years. During those times, I did what I had to do to get by. I taught myself web design and created Flash websites for clients. I rented my spare room on airbnb and became a Superhost. I took on consulting projects with various non-profits and foundations. Whatever I did, I never lost sight of the fact that I wanted to impact young people’s lives. Those “gigs” served a purpose. They’re not random ways to make money. They don’t just pay the rent. Instead, they gave me the support I needed to work on my own projects.

It’s important that things fit together, that there’s coherence to our pursuits, even when we are rebelling against simple and logical pathways. This is why we want the dots to connect, as Steve Jobs put it in his commencement address. We want to know our lives are guided by a sense of purpose, that there’s a through-line connecting one thing to another in an understandable way. Different words are used by different people — meaning, purpose, calling — but they get at the same idea.

Ultimately, we want a story of our life that makes sense to us and that we can be proud of. There are as many different stories as there are people. Some build their life and their story around what they love to do, others focus on people they care for or a cause they believe in. Everyone is on a different journey. That’s why it’s important to learn from others — how they build a unique life and tell their unique story — in order to make sense of our own.

We don’t usually know what the story is when we start out but it will naturally emerge as time goes on. For Steve Jobs, that coherent story will materialize if we stay connected to the things we love. “The only way to do great work is to love what you do,” Jobs said. “If you haven’t found it yet, keep looking. Don’t settle.”

At this point, some of you might think, “charting your own path is nice and all but it’s not for me.” You want clarity and certainty. You just want a job and career you can depend on and build a family with. There’s nothing wrong with getting a regular paycheck and climbing the corporate ladder in just one or two organizations. But even if you want to stay fixed to that goal, the world can change around you.

Had I stayed in journalism, I still would have had to make drastic changes in my life. Starting with Craigslist, online advertisement drained the revenue that sustained much of the news business. TV journalism has become more sensational and more dominated by talking heads providing commentary rather than news. Robots now write some of the stories that reporters used to write. Everyone with a smartphone is creating content. Nothing stands still. Even if I had stayed in the news business, I would have had to rethink what being a journalist is all about and find a new path forward. I would need to become a new type of journalist not just to get a paycheck, but to assure myself that I’m devoting my life to meaningful endeavors.

When you see yourself jumping from one gig to another or one job to another, don’t mistake it for hustling. It’s not about getting paid however you can. It’s not even about learning the latest technology and jumping on the latest trends. Something bigger is usually happening. What you’re really trying to figure out is your purpose. Purpose is what guides us when we venture into the unknown. Purpose is the compass we need when we have no maps.