Connecting the Dots of Our Lives

“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.”

Steve Job’s Stanford commencement address is one of those talks I rediscover perhaps once a year, watch twice in a row, feel that my life has changed, and then forget about a few days later. As much as I want to hold onto all that wisdom and let it change me, life always seems to get in the way.

I wrote recently about the difficulties with wanting to go abroad to do something different, to discover new interests and passions. To go abroad for study, for instance, requires an application that forces you to outline how this experience “aligns with your academic and career goals”. To be honest—to say simply that it doesn’t align, and that’s precisely the point—is to put you in a prisoner’s dilemma scenario with other applicants.

But I think that’s applicable not just to going abroad, but to what we want to do with our lives. Perhaps part of the reason I forget again and again about Jobs’ speech after feeling so deeply moved is that the daily reality of thinking about my future forces me to connect the dots looking forward.

Yale’s Office of Career Services recently asked me to send them my latest resume in order to talk through how it will set me up for the type of work I want to do over summer and after graduation. Through even requesting a resume, the question asked of us is not what do you want to do, but what can you do. The entire conversation is framed from there, with possibilities built on who we were rather than what we want to be and what we could be. We are incentivised by college career offices and employers to connect the dots looking forward, to extrapolate our pasts into our futures as if we were unchanging. That is a fallacy, an ever so costly one, and we must recognise that change is the point of our education. To leave college on the same path as one began leaves me wondering again what our time here was for.

A resume is the ultimate dot-connecter, and it requires that those dots are perfectly linear. I’ve heard from other students who went to their college career services office, who sat down with an adviser and were instantly labelled. “I can see from your resume that you will go into public policy”, the adviser says confidently, going off two previous public sector summer jobs the individual had listed.

Those summer jobs themselves were chosen by happenstance and serendipity! At age 20, to be told what career options are open to you based on a cumulative four months’ work! You wanted to be home one summer, you knew someone who offered you an interesting job, so you took it. Chance, fortuity; taking opportunities as they are presented: this is the right thing to do, and it is not connecting the dots forward. But to then be told by someone, supposedly a professional who knows how to best set you up for a career, that your dots will align only with a limited range of others… Your life’s work decided by happenstance!

I exaggerate, but perhaps only slightly.

And we know the answer were we to say, no, that’s not what I want to do with my life, in fact I want to be an artist and work on climate change. “But what experience do you have?” Job applications list as a requirement “former relevant work experience”. Your adviser tells you, “You’re competing for this museum curation job with other applicants who have spent the past three summers in that type of work. Why would they take you over them?” Friends and family say about your public policy job offer, “it’s a fantastic opportunity and a prestigious career, you should be pleased.” Resignedly, you decide that perhaps the public policy job wouldn’t be so bad. And so you connect one more summer’s dot, and as that line becomes longer it becomes yet more difficult to begin a new set of dots entirely. Each dot acts as a magnet, drawing yet more similar dots to it, and the more there are the stronger the magnetic field becomes. Two dots connect on your resume and decide the next fifty for you.

I exaggerate, but perhaps not much.

In class with David Brooks this semester we spent a few sessions discussing how to choose and shape a career. We were discussing careers in the traditional narrative of “needing the stars to line up”, in the same way that Jobs talked about your dots connecting. Someone frustratedly said “It’s not about how well the stars line up, but how creatively you draw a constellation between them.” I hadn’t heard that before, and it hit home.

The same advice is embedded in Jobs’ talk. From India to calligraphy to Mac OS is no path that a career adviser could ever have seen, or which Jobs could have put on a resume. “So you have to trust that the dots will somehow connect in your future.” He did what he felt was right, and later, after working out what he wanted to do, realised how these past experiences could make him better at whatever work he wanted to devote himself to. Had Jobs met with a career adviser or needed to apply for a job through a resume, where would he have ended up? What creativity, passion and talent would have been wasted?

We need to be aware of how our personal narratives and the lives they lead to are shaped by the structures of resumes and career thinking. Without understanding this, well-meaning career advice may hold us back from drawing a constellation between the dots of our lives, forcing us instead to draw an all-too-straight line between them.

The Two Yale-NUS Colleges

I’m sometimes asked what it is like to attend a university that is frequently in the headlines because of controversy. And it’s true: Yale-NUS College, where I am a member of the inaugural class, has been continually questioned and debated in public right from the start. Yale-NUS has been seen as a herald of the corruption of liberal values, where those poor students are censored and must be regretting their fated decisions to go there rather than Yale. We have been compared to blind puppies, and people have pitied our apparent lack of freedom.

But having spent this past semester at Yale in New Haven I’m struck by the fact that there are really two Yale-NUS Colleges. There’s the one that I attend, where student life is really just what I’ve had at Yale, where students have no need to take notice of the dire predictions made about our college’s fate. And there’s the other one, where Yale-NUS stands for the selling out of American liberal institutions. I read about the latter college in newspapers and online, and begin to pity those students myself. But I’ve certainly never encountered it in my three years at Yale-NUS College.

We should believe that Yale-NUS exists for an educational mission, and in that light what matters are the experiences that my classmates and I are having, over and above the abundance of interests and opinions that commentators on Yale-NUS seem to have. Each of us chose to attend Yale-NUS for very real reasons, unrelated to speculative controversy, and the College must be assessed against these reasons and hopes. For me, it was wanting a true liberal arts education in the Asia Pacific, an education that gave respect to narratives other than the American and Western European.

A recent Yale Daily News feature about Yale-NUS declared that “equally, if not more, important than how Yale-NUS’s watchers in New Haven view the partnership is what insiders — Singaporean politicians, peers at other local universities or patrons at Singapore’s signature food markets — think of the school.” Perhaps—but once again, this misses the point that Yale-NUS exists not for political and higher-ed insiders, let alone aunties and uncles at Singapore’s hawker centres. To juxtapose this with an equally crass stereotype, the equivalent would be a reporter from Singapore asking patrons of a Bojangles in Tennessee what they think of Yale. The response may not be quite what Yalies were hoping for, and ultimately those perspectives matter little to students’ lives.

The focus on the views of everyone other than students at Yale-NUS belies the false premise from which American commentators, as well as many students at Yale, approach the College. The frequent comparison between liberal Yale and authoritarian Singapore shows how Yale-NUS is often seen as a civilising mission, a grand scheme to indoctrinate Singapore from the inside, to end those restrictive chewing gum laws and ultimately allow gay marriage. These concerns demonstrate the confusion of liberal values with a liberal arts education, and I for one came to Yale-NUS for the latter.

Yale may believe it is exceptional, yet I’m inclined to read this exceptionalism as restricted to the realm of liberal arts education. As Yale’s own prospectus on Yale-NUS describes, “Creating an entirely new liberal arts college in Asia would allow Yale to extend to other parts of the world its long tradition of leadership in shaping liberal education.” One may disagree with even this goal, but it is a mistake to read it—as most critics of Yale-NUS seem to have done—as synonymous with a mission to inculcate liberal values in Singapore.

Within the realm of liberal education, however, the best people to ask about how Yale-NUS is shaping up are students themselves. The education I am receiving at Yale-NUS is practically identical in structure to that I’ve received this past semester at Yale: great professors from the world’s top universities, small seminars, a focus on debate and challenging other viewpoints. Where my education at Yale-NUS has differed is in the extent of those differences in viewpoints.

At Yale in New Haven the perspectives of other students that I’ve had to engage with have been centred around a common set of values. Differences of opinion on fundamental issues are really only minor differences around the edges of a topic, if those topics are even raised at all. At Yale-NUS, on the other hand, I have had to engage with viewpoints so different to my own that I have struggled to find language to respond. On topics from gay marriage and capital punishment to the role of the U.S. military in the world and the “Asian values” debate, I’ve been exposed to viewpoints that I always dismissed as being held by other people. To realise that these views are held by people I call friends is an education in itself, and has taught me necessary lessons about the diversity of the Asia Pacific.

When we focus on Yale-NUS’ mission to bring liberal arts education to the Asia Pacific, rather than liberal values, the irony is that I think Yale-NUS better lives up to its mission than Yale does. More often at Yale-NUS do I find myself deeply intellectually challenged, shocked at being face to face with a viewpoint so starkly different from my own, and forced to formulate a response that can be comprehended despite deep differences in fundamental perspectives.

Step back from the controversy, look at Yale-NUS for what it was intended to be and not what its critics say it should be, and then ask us about what it’s like studying the liberal arts in Asia. Yale-NUS is no longer an idea or an experiment, but is a real college with students who have very good reasons for attending. It’s time to start talking about the Yale-NUS that actually exists, not the one created from the minds of a small number of loud and eloquent commentators.

Why should we go abroad?: On connecting the dots of our lives

There were a few great lines about “finding yourself”, to use the cliche, in a Wall Street Journal article the other day. The article, titled “The College of Chinese Wisdom”, was wide-ranging and disparate, and I felt that the interpretations of Chinese philosophy for an American newspaper left something to be desired. But nevertheless an anecdote unrelated to Chinese philosophy in the middle of the piece left me thinking, and is worth quoting in full:

“Imagine a student who has decided he wants to become a diplomat. He’s always been great at mediating conflicts among his peers. He was involved in Model U.N. in high school, the international section is his favorite part of the newspaper, and he’s become pretty fluent in Spanish. He knows that majoring in international relations and taking his junior year abroad in Spain will give him the experiences that will propel him toward that career in diplomacy.

So he goes off to Spain, but after a month falls ill with a severe respiratory virus that lands him in the hospital. It is his first experience of hospitalization, and it plants a seed: He becomes curious about how and why doctors and hospitals do what they do.

Things can now go one of two ways. He can remain wedded to his long-term plan and let that interest in health care die out. The hospital experience will make for a few good stories for his friends, but it won’t interfere with his plan to take the diplomatic world by storm. Or he can keep diving into his new obsession, reading everything he can, maybe making friends with some of the young residents on his medical team, and eventually return to the U.S. and devote himself to a health-care field instead.

None of this has anything to do with the fact that he was in Spain; it’s just that one series of experiences led to another and opened up things to him that weren’t part of the plan. There’s nothing wrong with spending a year in Madrid or majoring in international relations. But there is something wrong with going abroad as part of a plan that fits in with a vision of who you already are and where you’re going.

Concrete, defined plans for life are abstract because they are made for a self who is abstract: a future self that you imagine based on a snapshot of yourself now. You are confined to what is in the best interests of the person you happen to be right now—not of the person you will become.” [Emphasis mine]

The difficulty comes in how the structures of our decisions are imposed on us from above. In his application to study abroad in Spain, the student will have had to outline how the experience will fit with his pre-defined goals. For instance, in my application to study abroad (I’m currently spending a semester abroad at Yale in the U.S.), I had to answer the following:

“Please explain why you are interested in studying abroad at this institution. Include in your answer a tentative list of courses that you would be interested in applying, and how might these courses help you achieve your academic and/or professional goals?” [Dodgy grammar was theirs, not mine]. 

We may well want study abroad to be a transformative experience, exposing us to new interests and ways we could live our lives, but taking this approach will make being accepted to the program far less likely. Institutions demand that we have our dots connected, so to speak—that where we are going aligns very neatly with where we have been and what we are doing at present.

A resume, for instance, which I was required to attach to my study abroad application, needs to show why the application makes sense for you. The truth could have been that I chose my study abroad precisely to do something entirely different, and yet my resume would then have had no narrative, and my responses to interview questions would have lacked the force of someone who had all their dots connected.

So I entirely agree that there is something wrong with going abroad as part of a plan that fits in with a vision of who you already are and where you’re going. And yet for students to take this advice to heart, to go abroad—or choose jobs—with ideas about what they could become and where they might go will require acceptance of this approach by overarching institutions. It is not students’ mindsets that are the problem, but rather the structures of decision making and narrative building that are imposed on students by long-standing institutions. The structure of a resume dictates the possibilities that are open to us.

Perhaps the risk should simply be taken, the questions answered honestly: I want to go abroad to do something I have never done before, something that might not make sense for my academic and professional goals but which I think I should try nonetheless. It’s prisoner’s dilemma, of course. The students who take the chance risk losing out over the students who answered the questions by connecting the dots of their lives. But ultimately losing out in an application that aligns your life along one straight path might be precisely the opportunity you needed to do something transformative that you had no seemingly good reason to do.


Thanks to Maria for sending me the link to the WSJ article.